Day: April 7, 2022

Computed Properties of C8H8N2S. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 2-Mercapto-5-methylbenzimidazole, is researched, Molecular C8H8N2S, CAS is 27231-36-3, about Toxicity Study of a Rubber Antioxidant, Mixture of 2-Mercaptomethylbenzimidazoles, by Repeated Oral Administration to Rats. Author is Saitoh, M.; Umemura, T.; Kawasaki, Y.; Momma, J.; Matsushima, Y.; Sakemi, K.; Isama, K.; Kitajima, S.; Ogawa, Y.; Hasegawa, R.; Suzuki, T.; Hayashi, M.; Inoue, T.; Ohno, Y.; Sofuni, T.; Kurokawa, Y.; Tsuda, M..

2-Mercaptobenzimidazole (2-MBI), a rubber antioxidant, is known to exhibit potent antithyroid toxicity in rats and is a candidate as an environmental endocrine disrupter. 2-Mercaptomethylbenzimidazoles (a 1:1 mixture of 4-Me and 5-Me isomers, MMBIs), are also employed industrially as rubber antioxidants and are suspected to exert antithyroid toxicity such as 2-MBI. In this investigation, acute and subacute oral toxicity studies of MMBIs in Wistar rats were conducted. The clin. signs of acute oral toxicity were observed including decreased spontaneous movement, a paralytic gait, salivation and lacrimation, and adoption of prone and lateral positions. The LD50 was estimated to be 330 mg/kg. In the subacute oral toxicity study, male and female rats were treated with MMBIs by gavage at doses of 0 (corn oil), 4, 20 and 100 mg/kg for 28 consecutive days followed by a 2-wk recovery period for the control and highest dose groups. Body weight and food consumption, clin. signs, organ weights, clin. biochem. and hematol. parameters including clotting times and micronuclei induction in bone marrow erythropoietic cells, and histopathol. were examined Relative organ weights of lung, liver and kidney, and serum cholesterol and phospholipid significantly increased in male rats treated with MMBIs at doses of 20 and 100 mg/kg. Male rats administered 100 mg/kg MMBIs exhibited a 1.8-fold increase in thyroid weight associated with histopathol. changes but not altered serum thyroid hormone levels. Female rats administered 100 mg MMBIs/kg exhibited significant increases of liver and kidney but not thyroid weights, and serum cholesterol level. The antithyroid toxicity of MMBIs in rats was estimated to be one-tenth that of 2-MBI. No-observed-effect levels for male and female rats were found to be 4 and 20 mg/kg, resp., in this subacute oral toxicity study.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Robinson, Anthony L.; Boss, Paul K.; Heymann, Hildegarde; Solomon, Peter S.; Trengove, Robert D. researched the compound: 1-(Furan-2-yl)propan-1-one( cas:3194-15-8 ).Application of 3194-15-8.They published the article 《Development of a sensitive non-targeted method for characterizing the wine volatile profile using headspace solid-phase microextraction comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry》 about this compound( cas:3194-15-8 ) in Journal of Chromatography A. Keywords: wine flavor headspace solid microextraction GC MS. We’ll tell you more about this compound (cas:3194-15-8).

Future understanding of differences in the composition and sensory attributes of wines require improved anal. methods which allow the monitoring of a large number of volatiles including those present at low concentrations This study presents the optimization and application of a headspace solid-phase microextraction (HS-SPME) method for anal. of wine volatiles by comprehensive two-dimensional gas chromatog. (GC × GC) time-of-flight mass spectrometry (TOFMS). This study demonstrates an important advancement in wine volatile anal. as the method allows for the simultaneous anal. of a significantly larger number of compounds found in the wine headspace compared to other current single dimensional GC-MS methodologies. The methodol. allowed for the simultaneous anal. of over 350 different tentatively identified volatile and semi-volatile compounds found in the wine headspace. These included potent aroma compound classes such as monoterpenes, norisoprenoids, sesquiterpenes, and alkyl-methoxypyrazines which have been documented to contribute to wine aroma. It is intended that wine aroma research and wine sensory research will utilize this non-targeted method to assess compositional differences in the wine volatile profile.

Compound(3194-15-8)Application of 3194-15-8 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(1-(Furan-2-yl)propan-1-one), if you are interested, you can check out my other related articles.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

COA of Formula: C38H24F4O4P2. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, is researched, Molecular C38H24F4O4P2, CAS is 503538-69-0, about Pd/Zn Co-catalyzed Asymmetric Ring-opening Reactions of Aza/Oxabicyclic Alkenes with Oximes. Author is Shen, Guoli; Khan, Ruhima; Yang, Fan; Yang, Yong; Pu, Dongdong; Gao, Yang; Zhan, Yong; Luo, Yang; Fan, Baomin.

An application of various oximes as nucleophiles in the asym. ring-opening (ARO) reaction of aza/oxabicyclic alkenes resulting in cis-ARO products has been developed. The reaction was co-catalyzed by Pd(OAc)2 and Zn(OTf)2 with (R)-DIFLUORPHOS as the chiral ligand. This methodol. exhibits broad substrate scope, functional group tolerance with high enantioselectivity. A synthetic application of this method has been demonstrated.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(Furan-2-yl)propan-1-one( cas:3194-15-8 ) is researched.Category: benzoxazole.Paravisini, Laurianne; Prot, Aurelie; Gouttefangeas, Cecile; Moretton, Cedric; Nigay, Henri; Dacremont, Catherine; Guichard, Elisabeth published the article 《Characterisation of the volatile fraction of aromatic caramel using heart-cutting multidimensional gas chromatography》 about this compound( cas:3194-15-8 ) in Food Chemistry. Keywords: caramel cooking aroma volatile furan lactone acid; Caramel; Heart-cutting multidimensional gas chromatography (MDGC); Mass Spectrometry; Odorant compounds; Olfactometry. Let’s learn more about this compound (cas:3194-15-8).

The first aim of the study was to improve characterization of the volatile fraction of aromatic caramel by applying heart-cutting multidimensional gas chromatog. coupled to mass spectrometry and olfactometry (MDGC-MS-O) on targeted odorant fractions. The second aim was to compare the volatile composition of two caramel samples, which differed in terms of their carbohydrate composition and cooking process. MDGC analyses enabled identification of 37 compounds (17 with the addition of pure standard) in the burnt sugar caramel, 20 of which were reported for the first time in caramel. Fifteen compounds were identified as odor-active and described using a range of attributes such as floral, roasted, spicy and almond. Furans, lactones and acids resulting from the thermal breakdown of sugars predominated in the volatile fraction of the burnt sugar caramel, due to the harsher cooking conditions. These results have enabled a clearer understanding of aromatic caramel as well as the identification of new compounds which might make an important contribution to its aroma.

Compound(3194-15-8)Category: benzoxazole received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(1-(Furan-2-yl)propan-1-one), if you are interested, you can check out my other related articles.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Synthetic Route of C9H9NO. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Ag@TiO2 nanocomposite; synthesis, characterization and its application as a novel and recyclable catalyst for the one-pot synthesis of benzoxazole derivatives in aqueous media. Author is Maleki, Behrooz; Baghayeri, Mehdi; Vahdat, Seyed Mohammad; Mohammadzadeh, Abbas; Akhoondi, Somaieh.

A series of benzoxazole derivatives I (R = H, 3-NO2C6H4, CH2CH3, 3-CH3OC6H4, etc.) were synthesized via Ag@TiO2 nanocomposite catalyzed one-pot condensation of 2-aminophenol and several aromatic aldehydes or orthoesters or carboxylic acids or amides or acyl chlorides in water at room temperature with excellent yields. The short reaction times, high yields, safety and mild conditions, simplicity, non-toxicity and easy workup were the main merits of this protocol.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Category: benzoxazole. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1-(Furan-2-yl)propan-1-one, is researched, Molecular C7H8O2, CAS is 3194-15-8, about 1,4-Addition in the furan series. I. Condensation of benzylmagnesium bromide with α-furyl ketones. Author is Berreby, Edgar; Morizur, Jean P.; Wiemann, Joseph.

A mixture of 27.5 g. 2-acetylfuran in 50 cc. ether was refluxed 1 hr. with PhCH2MgBr prepared from 42.75 g. PhCH2Br and hydrolyzed with HCl to give 10 g. of the starting material and 34 g. of a mixture, b0.01 82-92°. This mixture was redistilled to give 18% dibenzyl, b5 115-17°, 20% 1-phenyl-2-furyl-2-propanol, b5 123°, and 30% 2-acetyl-3-benzyl-2,3-dihydrofuran, b7 131°. Similar treatment of ethyl 2-furyl ketone gave 31.5 g. of a mixture containing 11% dibenzyl, 24% 1-phenyl-2-furyl-2-butanol, b6 136°, and 24% 2-propionyl-3-benzyl-2,3-dihydrofuran, b6 131°. N.M.R. and ir data are given.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 503538-69-0, is researched, SMILESS is FC1(F)OC2=CC=C(P(C3=CC=CC=C3)C4=CC=CC=C4)C(C5=C6OC(F)(F)OC6=CC=C5P(C7=CC=CC=C7)C8=CC=CC=C8)=C2O1, Molecular C38H24F4O4P2Journal, Article, Research Support, Non-U.S. Gov’t, Journal of the American Chemical Society called Access to enantioenriched α-amino esters via rhodium-catalyzed 1,4-addition/enantioselective protonation, Author is Navarre, Laure; Martinez, Remi; Genet, Jean-Pierre; Darses, Sylvain, the main research direction is amino acid ester asym preparation; aryltrifluoroborate amino acrylate conjugate addition protonation rhodium.Recommanded Product: 503538-69-0.

Conjugate addition of potassium trifluoro(organo)borates to dehydroalanine derivatives, mediated by a chiral rhodium catalyst and in situ enantioselective protonation, afforded straightforward access to a variety of protected α-amino esters with high yields and enantiomeric excesses up to 95%. Among the tested chiral ligands and proton sources, Binap, in combination with guaiacol (2-methoxyphenol), an inexpensive and nontoxic phenol, afforded the highest asym. inductions. Organostannanes have also shown to participate in this reaction. By a fine-tuning of the ester moiety, and using Difluorophos as chiral ligand, increased levels of enantioselectivity, generally close to 95%, were achieved. Deuterium labeling experiments revealed, and DFT calculation supported, an unusual mechanism involving a hydride transfer from the amido substituent to the α carbon explaining the high levels of enantioselectivity attained in controlling this α chiral center.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reduction of α-furyl ketones by chemical methods at different potentials. Properties and physical-chemical studies of the different compounds obtained》. Authors are Morizur, Jean Pierre; Wiemann, Joseph.The article about the compound:1-(Furan-2-yl)propan-1-onecas:3194-15-8,SMILESS:O=C(C1=CC=CO1)CC).Electric Literature of C7H8O2. Through the article, more information about this compound (cas:3194-15-8) is conveyed.

α-Furyl alkyl ketones were reduced by Zn (E0  0.75 v.) in AcOH, Mg (E0 = 2.5 v.) in AcOH, and Na amalgam (E0 = 2.7 v.) in H2O. The products were characterized by infrared (IR) and nuclear magnetic resonance (NMR) spectra. The following ketones were prepared by known methods [alkyl group and b.p. (mm.) given]: Me (I), 69° (15); Et (II), 74-6° (11); Pr (III), 96° (20). To a stirred suspension of 50 g. Zn in 500 ml. H2O at 50° was added over 3 hrs. 1 mole ketone in 100 g. AcOH simultaneously with 50 g. Zn and the mixture stirred 1 hr. to give the following results. I gave 2.5 g. IV, b0.05 80-2°, m. 121-2° (benzene), and 27.5 g. 2,3-di-2-furylbutane-2,3-diol (V), b0.05 92-4°. II and III gave, resp., 25 g. 3,4-di-2-furylhexane-3,4-diol (VI), b0.05 96-8°, and 28 g. 4,5-di-2-furyloctane-4,5-diol (VII), b0.05 104-6°. To a stirred mixture of 1 mole ketone in 500 ml. H2O at 100°, 72 g. Mg was added in small portions with dropwise addition of 400 g. 90% AcOH over 6 hrs. to give (from I) 5 g. IV, 27 g. V, and 32 g. VIII (R = Me), b0.05 102-5°, (from II) 30 g. VI, 36 g. VIII (R = Et), b0.05 106-9°, and (from III) 15 g. VII, 18 g. VIII (R = Pr), b0.05 111-13°. One mole I was reduced at -35° by 34.5 g. Na as an amalgam ( CA 55, 363d) to give 8 g. IV, 7 g. V, m. 47-8°, and 3 g. VIII (R  Me). Hydrogenation of IV by LiAlH4 in ice-cold Et2O gave IX, m. 98-100° (benzene). Similar treatment of the γ-ketols gave dihydroxy compounds melting over a 30-40° range.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Saha, Prasenjit; Ramana, Tamminana; Purkait, Nibadita; Ali, Ashif Md; Paul, Rajesh; Punniyamurthy, Tharmalingam published the article 《Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles》. Keywords: benzimidazole aminobenzimidazole aminobenzothiazole benzoxazole preparation; intramol cyclization bromoaryl derivative copper oxide nanoparticle catalyst.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Product Details of 6797-13-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

The synthesis of substituted benzimidazoles, 2-aminobenzimidazoles, 2-aminobenzothiazoles, and benzoxazoles is described via intramol. cyclization of o-bromoaryl derivatives using copper(II) oxide nanoparticles in DMSO under air. E.g., cyclization of o-bromoaryl amidine I gave 95% benzimidazoles II. The procedure is exptl. simple, general, efficient, and free from addition of external chelating ligands. It is a heterogeneous process and the copper(II) oxide nanoparticles can be recovered and recycled without loss of activity.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Chain-substituted methinecyanines and styryl dyes, published in 1956, which mentions a compound: 6797-13-3, mainly applied to , Formula: C9H9NO.

Various methinecyanines carrying a substituent on the chain have been prepared and their absorption maximum compared with those of the parent dyes. The procedure of Schott [Ber. 29, 1985(1896)] in which PhCH2CO2H (I) and PCl5 were reported to give PhCH2COCl (II) could not be reproduced. Instead, to 18 cc. boiling SOCl2 was added in 10 min. 27.2 g. I, the whole refluxed 0.5 hr. and distilled to give 77% II, b17 96-8°. To 17.8 g. II and 1 equivalent o-HSC6H4NH2.HCl was added 0.33 mole P2O5, the whole heated 8 min. in an oil bath at 160-175°, warmed with aqueous NaOH, the whole cooled, extracted with Et2O, and the Et2O extracts concentrated and distilled to give 29% 2-benzylbenzothiazole (III), b0.5 157-63°. III (9.82 g.) and 1.2 equivalents EtI heated 48 hrs. at 100° and the mixture treated with Me2CO gave 57% of the ethiodide (IV), yellow crystals, m. 181° (from EtOH). In similar fashion, were prepared 73% 2-(p-nitrobenzyl)benzothiazole, m. 115° (from EtOH) [ethiodide (V), m. 249° (decomposition)(from MeOH)] and 18% 2-(chloromethyl)benzothiazole (VA), b0.2 79-91°, m. 34° (from petr. ether); VA and EtI gave no ethiodide. To 20.85 g. Zn salt of o-H2NC6H4SH in 90 cc. boiling dry C6H6 was added gradually 1 equivalent EtO2CCOCl (VI) (b21 75-8°) in 120 cc. dry C6H6, the whole refluxed 6 hrs., filtered, the insoluble residue extracted with boiling C6H6, the C6H6 filtrates and extracts combined, washed with excess aqueous NaHCO3, washed with H2O, dried, and distilled to give 2-ethoxycarbonylmethylbenzothiazole (VIA), yellow liquid, b0.5 121-26° [methiodide (VII), m. 175° (decomposition) (from MeOH-Me2CO); ethiodide (VIII), m. 190° (decomposition) (from EtOH)]. To 0.81 g. o-HSC6H4NHEt (IX) in 4 cc. dry C6H6 was added 1.1 equivalent VI in 2 cc. dry C6H6, the whole cooled to room temperature, the liquid decanted, the gum washed with C6H6, the C6H6-insoluble residue dissolved in 2 cc. MeOH, and the MeOH solution treated with a warm solution of 2 equivalent KI in 4 cc. H2O to give VIII. By the same procedure, IX and ClCH2COCl in C6H6, followed by KI gave 13-19% 2-(o-ethylaminophenylthiomethyl)benzothiazole ethiodide (IXA), m. 158° (decomposition) (from MeOH). 2-Ethylthiobenzothiazole (X) 19.93 g. and 1 equivalent neutral Et2SO4 heated 8 hrs. at 110-20°, the whole dissolved in 120 cc. H2O, the solution extracted with Et2O, the aqueous solution separated, cooled, and treated with an excess of NaOH gave 30-83% 3-ethyl-2-oxobenzothiazoline (XI), colorless liquid, b0.5 101° (a contaminant which was difficult to sep. from XI was 3-ethyl-2-thiobenzothiazoline (XII)). X (19.5 g.) and 1 equivalent Et2SO4 heated 8 hrs. at 110-20°, the whole dissolved in 100 cc. C5H5N, and the solution refluxed 1 hr. and poured into warm H2O gave 82% XII, m. 77-8° (from MeOH). Freshly prepared 2-ethylthiobenzothiazole.EtI (XIII) 0.63 g. and 3 cc. C5H5N refluxed 10 min. and the whole poured into 12 cc. H2O gave 68% XII. On standing for several months, XIII was gradually converted to XII. Distilled XI (12.1 g.) in 24 cc. EtOH and 6 equivalents KOH in 70 cc. EtOH refluxed 1 hr., cooled, the K2CO3 filtered, the filtrate evaporated to dryness, the residue dissolved in 100 cc. H2O, the H2O solution cooled and made acidic with concentrated HCl, the oily product extracted with C6H6, and the C6H6 solution dried, concentrated, and distilled gave 77% IX, b0.5 57-60°. XII (19.53 g.) in 40 cc. EtOH and 6 equivalents KOH in 105 cc. EtOH refluxed 6 hrs. and treated as above gave 70% IX. o-H2NC6H4OH (XIV) 42.6 g. was added slowly to 3 equivalents (EtCO)2O, the whole was heated 0.5 hr. on a H2O bath, then distilled from an oil bath, rejecting material b. below 150°. The residual material was washed thoroughly with 10% Na2CO3 solution, separated, and distilled to give 28% 2-ethylbenzoxazole (XIVA), b0.3-0.5 40-3°; ethiodide (XV), colorless crystals, m. 198° (decomposition) (from EtOH). XIV (10.9 g.) and 1 equivalent PhCH2CO2H heated 3 hrs. at 200-25° (H2O vapor allowed to distil), the mixture cooled, treated with aqueous NaOH, extracted with C6H6, and the C6H6 solution concentrated and distilled gave 48% 2-benzylbenzoxazole (XVA), b0.3 118-25°; no ethiodide could be prepared and the Et p-toluene-sulfonate (XVI) was a gum which could be dissolved in EtOH and used in the dye condensations described below. To 1 mole 2-ethylbenzothiazole-EtI (XVII) and 1 mole 2-iodoquinoline-EtI (XVIII) in EtOH there was added 2.1 moles Et3N. The mixture stirred and refluxed 1-30 min., the whole cooled, treated with Et2O, the precipitated gum separated, and washed with Et2O gave 54-84% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]methylmethinecyanine iodide (XIX), olive-green dye, softens 125°, m. about 148° (from Me2CO and from EtOH). XIX was homogeneous as shown by a chromatogram from CHCl3 on alumina. XIX had a slight desensitizing action toward a photographic emulsion. In a similar experiment with 2-ethylbenzothiazole-p-MeC6H4SO3Et (XIXA), the gum precipitated with Et2O and heated with aqueous KI gave 66% XIX. XVII (0.8 g.) and 2-ethylthioquinoline reacted as above gave a mixture of 12% XIX and a trace of [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]methinecyanine iodide, separated by absorption on alumina and elution with CHCl3-EtOH. In a similar fashion, XVII and XIII gave 8% bis[2-(3-ethylbenzothiazole)]methylmethinecyanine iodide, brick-red crystals, m. about 214° and a trace of the bis[2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]phenylmethinecyanine iodide (from EtOH); 2-methylbenzothiazole-EtI and 2-iodo-5,6-benzoquinoline-EtI (XX) gave 42% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]methinecyanine iodide, red-orange crystals, m. 258° (decomposition) (from MeOH); XVII and XX gave 67% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]methylmethinecyanine iodide, dark-purple crystals, m. about 225° (violent decomposition) (from EtOH); XIII and XX gave 42% [2-(1-ethyl-5,6-benzoquinoline)][2-(3-ethylbenzothiazole)]phenylmethinecyanine iodide, purple crystals, m. about 175° (decomposition) (from EtOH); XVII and 1-iodoisoquinoline-EtI (XXI) gave the dye iodide, which in hot EtOH with hot aqueous NaClO4 gave 72% [2-(3-ethylbenzothiazole)][1-(2-ethylisoquinoline)]-methylmethinecyanine perchlorate, vermillion crystals, m. about 164° (decomposition) (from EtOH); III and XXI gave 36% [2-(3-ethylbenzothiazole)][1-(2-ethylisoquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 227° (decomposition) (from EtOH); and XIXA and 4-iodoquinoline.EtI (XXII) (the reaction mixture after 2-min. reflux was treated with aqueous KI) gave 49% [2-(3-ethylbenzothiazole)][4-(1-ethylquinoline)]methylmethinecyanine iodide (XXIII), olive-green crystals, m. 185° (decomposition) (from EtOH). XVII 1 mole, 3 moles quinoline-EtI, 3 moles KOH, and EtOH refluxed 0.5 hr., the solid (XXIV) filtered, the XXIV (apocyanines) boiled with 25 cc. EtOH, the solid (XXV) filtered, washed with 5 cc. hot EtOH, the combined filtrate and washings cooled gave 8% erythroapocyanine (XXVI); the XXV represented 0.5% xanthoapocyanine (XXVII) (see below); quinoline-EtI in boiling MeOH-KOH gave 31% XXIV; the XXIV extracted with boiling EtOH left 0.5% XXVII [[2-(1-ethylquinoline)][3-(1-ethylquinoline)]cyanine iodide]; the EtOH extracts were concentrated to give 14% XXVI [[3-(1-ethylquinoline)][4-(1-ethylquinoline)]cyanine iodide], m. 215-20° (decomposition) (from EtOH), λmaximum 5160 A. (ε 31,600) (in MeOH). Quinoline-EtI (7 g.) in 140 cc. EtOH and 2.76 g. Na in 20 cc. EtOH refluxed 1 hr. and the solid filtered gave 5% XXVII, orange crystals, m. >305° (from MeOH), λmaximum 4610 A., 3620 A. (ε 19,900, 6200). To IV and XXII in EtOH was added 180-mesh anhydrous K2CO3 and the whole refluxed 2 min. to give 56% [2-(3-ethylbenzothiazole)] [4-(1-ethylquinoline)] phenylmethinecyanine iodide, m. about 222° (decomposition) (from EtOH and from MeOH). V and p-MeC6H4SO3Et heated 4 hrs. at 165-75°, the product dissolved in hot EtOH, and then treated with XVIII gave the crude iodide (XXVIII) as a gum; XXVIII in CHCl3 chromatographed on alumina and eluted with CHCl3-EtOH (99:1)gave 6% [2-(3-ethylbenzothiazole)] [2-(1-ethylquinoline)]-p-nitrophenylmethinecyanine iodide, dark-purple crystals, m. 216° (decomposition) (from EtOH). 2-Ethylthioquinoline and Et2SO4 heated 8 hrs. at 110-20°, the salt in hot EtOH, VIA, and Et3N refluxed-5 min., the whole acidified with HCl, treated with NaClO4 in hot H2O, the whole cooled, the orange tar freed of liquid, washed well with hot H2O, and while wet dissolved in hot MeOH gave 66% perchlorate salt (XXIX), red crystals, m. 195° (decomposition). XXIX triturated with aqueous NaOH, the whole extracted with C6H6, the C6H6 extracts dried and concentrated, the residue dissolved in hot C6H6, the solution filtered, and the filtrate diluted with pert. ether gave 51% ethoxycarbonylmethine[2-benzothiazole] [2-(1-ethyldihydroquinoline)] (XXX), black crystals, m. 179° (decomposition), λmaximum 5170 A. (ε 13,500) (in MeOH containing NH3), λmaximum 3290 A., 4780 A. (ε 41,500, 8100) (in MeOH containing H2SO4). Similarly, X (0.98 g.) and Et2SO4 heated 8 hrs. at 110-20° and the salt (XXXI) reacted with VIA as above gave 79% perchlorate, m. 137° (decomposition) (from MeOH), which yielded 65% ethoxycarbonylmethine[2-benzothiazole][2-(3-ethyl-2,3-dihydrobenzothiazole)] (XXXII), pale-yellow crystals, m. 127° (from C6H6-petr. ether), λmaximum 3430 A. (ε 17,500) (in MeOH containing NH3), λmaximum 4230 A. (ε 9110) (in MeOH containing H2SO4). XXX and MeI heated 24 hrs. at 100°, the product washed first with hot C6H6 and then with aqueous NaHCO3, gave 25% [2-(1-ethylquinoline)] [2-(3-methyl-benzothiazole)]ethoxycarbonylmethinecyanine iodide, red crystals, m. 206° (decomposition). XXX and EtI similarly gave 32% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)]-ethoxycarbonylmethinecyanine iodide, orange crystals, m. 190° (decomposition) (from aqueous MeOH). XXXI, as above, and 2-methylbenzothiazole-p-MeC6H4SO3Me gave 41% [2-(3-ethylbenzothiazole)] [2-(3-methylbenzothiazole)]methinecyanine iodide, pale-yellow crystals, m. 287° (decomposition) (from EtOH). XXXII and MeI gave 25% [2-(3-ethylbenzothiazole)] [2-(3-methylbenzothiazole)]ethoxycarbonylmethinecyanine, pale-yellow crystals, m. 224° (decomposition) (from MeOH); while XXXII and EtI gave 45% [bis-2-(3-ethylbenzothiazole)]ethoxycarbonylmethinecyanine iodide, yellow crystals, m. 218° (decomposition) (from MeOH). Dibenzothiazolylmethane-EtI (XXXIIA), XVIII, Et3N, and EtOH gave 20% [2-(3-ethylbenzothiazole)][2-(1-ethylquinoline)](2-benzothiazolyl)methinecyanine iodide, purple crystals, m. 232°. 2-Methylbenzoxazole-EtI (XXXIII) and XVIII gave 15% [2-(3-ethylbenzoxazole)][2-(1-ethylquinoline)]methinecyanine iodide, yellow crystals, m. 277° (decomposition) (from EtOH). XV and XVIII gave an unstable iodide dye, maroon crystals, m. 133° (decomposition) (from EtOH). XVI and XVIII similarly gave 26% [2-(3-ethylbenzoxazole)] [2-(1-ethylquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 227° (decomposition) (from EtOH). 2-Ethylthiobenzoxazole, 2-methyl-5,6-benzoquinoline, and p-MeC6H4SO3Et heated 3.5 hrs. at 150-60°, the gum dissolved in 15 cc. hot EtOH and treated with aqueous KI gave 17% [2-(1-ethyl-5,6-benzoquinoline)] [2-(3-ethylbenzoxazole)]-methinecyanine iodide (XXXIV), m. 275° (decomposition) (from MeOH), λmaximum 4630, 4450 A. (ε 50,300, 49,400); alternatively, XX and XXXIII gave 3% XXXIV along with bis-2-(1-ethyl-5,6-benzoquinoline)methinecyanine iodide, m. 310° (decomposition). XVI and XX gave 2% [2-(1-ethyl-5,6-benzoquinoline)] [2-(3-ethylbenzoxazole)]phenylmethinecyanine iodide, red crystals, m. 183° (decomposition); XXI and 2-methylbenzoxazole-p-MeC6H4SO3Et gave 37% [2-(3-ethylbenzoxazole)][1-(2-ethylisoquinoline) ]methinecyanine iodide, red crystals, m. 228° (decomposition) (from EtOH). XVA by similar reactions (a) with XXI gave 27% of the corresponding phenylcyanine iodide, vermilion crystals, m. about 180° (decomposition) (from EtOH) and (b) with XXII 4% [2-(3-ethylbenzoxazole)] [4-(1-ethylquinoline)]phenylmethinecyanine iodide, maroon crystals, m. 224° (decomposition) (from Me2CO and from EtOH). The following compounds are derivatives of XXXV and XXXVI. 2-Methylbenzothiazole-EtI, p-Et2NC6H4CHO (XXXVII), and Ac2O were refluxed 20 min., the whole poured into a hot solution of KI in H2O, and the solid filtered and washed with Et2O to give 62% XXXV (R = H, R’ = Et) (XXXVIII), indigo-blue crystals, m. 225° (decomposition) (from MeOH). Similarly, XVII and XXXVII gave 57% XXXV (R = R’ = Me) (XXXIX), dark-blue crystals, m. 197° (decomposition) (from EtOH). The Et2O washings were evaporated, the residue dissolved in hot C6H6, and the C6H6 solution diluted with an equal volume of petr. ether to give 6% 3-ethyl-2-[2-(4-iminocyclohexa-2,5-dienylidene)-l-methylethylidene] benzothiazoline (XL), yellow crystals, m. 160°, λmaximum 3840 A. (ε 15,400). 2-Ethylbenzothiazole-EtI and XXXVII gave 18% XXXV (R = Me, R’ = Et), red crystals, m. 192° (decomposition), a trace of XXXVIII and, as above, the ethylimino analog of XL, m. 137° (from EtOH), λmaximum 3930 A. (ε 13,600). IV and Me2NC5H4CHO (XLI) gave 63% XXXV (R = Ph, R’ = Me), red crystals, m. about 180° (decomposition) (from AcOH). V and XLI gave 26% XXV (R = p-O2NC6H4, R’ = Et), terra cotta crystals, m. 203° (decomposition)(from MeOH) and the 1-(p-nitrophenyl)ethylidene analog of XL, yellow crystals, m. 220° (from Ac2O). VIII and XLI gave 24% XXXV (R = EtO2C, R’ = Me), orange crystals, m. 199° (decomposition) (from EtOH). XXXIIA and XLI gave 43% XXXV (R = 2-benzothiazolyl, R’ = Me), red crystals, m. 210° (decomposition) (from MeOH). To 2-methylbenzoxazole-p-MeC6H4SO3Et and XLI in hot EtOH was added Et3N, the whole refluxed 3 hrs., cooled, diluted with Et2O, the red tar separated, dissolved in MeOH, and the MeOH diluted with EtI in H2O gave 30% XXXVI (R = H, R’ = Me), red crystals, m. 251° (decomposition) (from EtOH). XV (1.52 g.) and XLI in Ac2O as above gave XXXVI (R = R’ = Me), red crystals, m. 210° (decomposition) (from MeOH). XVI and XLI gave XXXVI (R = Ph, R’ = Me), vermilion crystals, m. 223° (decomposition) (from EtOH). The effect of structure of these dyes on ultraviolet absorption as well as bathochromic shift is discussed.

Compound(6797-13-3)Formula: C9H9NO received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(2-Ethylbenzo[d]oxazole), if you are interested, you can check out my other related articles.

Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem