95-21-6

Usage

Uses

Used in Organic Synthesis:
2-Methylbenzoxazole is utilized as a key intermediate in the synthesis of various organic compounds, including bis-styryl dyes. Its unique chemical structure allows it to serve as a valuable building block in the development of new and innovative molecules.
Used in Pharmaceutical Industry:
In the field of medicine, 2-Methylbenzoxazole is employed as a precursor for the synthesis of pharmaceutical compounds. Its versatile chemical properties make it suitable for the development of new drugs and therapeutic agents.
Used in Fragrance Industry:
Due to its distinctive tobacco-like aroma, 2-Methylbenzoxazole is used as a fragrance ingredient in the perfumery and cosmetics industry. Its high strength odor makes it a valuable addition to various scent formulations.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 675, 1996 DOI: 10.1016/0040-4039(95)02240-6

Biochem/physiol Actions

Odor at 1.0%: Musty, nutty pecan, almond and pistachio-like, tobacco, vanilla-like with brown roasted burnt rubber and cooked rice-like nuances.Taste at 2.0ppm: Musty, nutty, vanilla and rice-like.

InChI:InChI=1/C8H7NO/c1-6-9-7-4-2-3-5-8(7)10-6/h2-5H,1H3

Upstream product

• 5467-64-1 2-acetamidophenyl acetate 
• 108-24-7 acetic anhydride 
• 95-55-6 2-amino-phenol 
• 141-97-9 ethyl acetoacetate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 
• 32894-07-8 S-benzyl thioacetimidate hydrochloride 
• 71607-45-9 N,N-Diphenyl-acetamidine 
• 103-79-7 1-phenyl-acetone 
• 688-71-1 tri-n-propyl borate 
• 614-80-2 2-(acetylamino)phenol 
• 51-19-4 2-aminophenol hydrochloride 
• 75-05-8 acetonitrile 
• 88-75-5 2-hydroxynitrobenzene 

Downstream Products

• 15185-40-7 bis-(3-ethyl-benzoxazol-2-yl)-methinium ; iodide 
• 68006-75-7 (3-ethyl-benzothiazol-2-yl)-(3-ethyl-benzoxazol-2-yl)-methinium ; iodide 
• 111563-19-0 (3-methyl-benzoxazol-2-yl)-(4-methyl-3-phenyl-thiazol-2-yl)-methinium ; iodide 
• 19560-88-4 2-(benzo[d]oxazol-2-yl)-1-phenylethan-1-one 
• 75220-88-1 1,4-bis<β-(2-benzoxazolyl)vinyl>benzene 
• 59066-62-5 (E)-2-styrylbenzoxazole 
• 83318-25-6 2-(β-phenylethyl)benzoxazole 
• 71907-23-8 2‐[(E)‐2‐(4‐methoxyphenyl)ethenyl]‐1,3‐benzoxazole 
• 24675-13-6 (E)-4-(2-(benzo[d]oxazol-2-yl)vinyl)-N,N-dimethylaniline 
• 32901-39-6 5-methyl-4-[(3-methyl-3H-benzoxazol-2-yliden)-ethylidene]-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 110377-14-5 3-ethyl-2-(3,5,5-trimethyl-cyclohex-2-enylidenemethyl)-benzoxazolium; iodide 
• 573-27-3 2-(N-acetyl-N-methylamino)phenol 
• 5260-36-6 2,3-dimethylbenzoxazolium iodide 
• 21598-08-3 benzoxazole-2-carboxylic acid 

Relevant academic research and scientific papers

Disubstituted Ferrocenyl Iodo- And Chalcogenoalkynes as Chiral Halogen and Chalcogen Bond Donors

Asymmetric catalysis based on halogen and chalcogen bonds (XB and ChB) is in its infancy, and the search for new chiral XB and ChB donors represents a crucial step toward its development. In this context, we designed and prepared new motifs containing three key substructures: namely, regions of electron charge density depletion centered on iodine and chalcogen atoms, the ethynyl functionality, and the planar chiral ferrocenyl platform. Nine ferrocenyl iodoalkynes were prepared as pure enantiomers by asymmetric synthesis. The XB donor property of racemic ferrocenyl iodoalkynes was demonstrated in solution in two benchmark reactions: the Ritter reaction and the benzoxazole synthesis from thioamides. In contrast, the ferrocenyl chalcogenoalkynes were far less active in these reactions. The potential of racemic and enantiopure ferrocenyl iodoalkynes as XB donors was also confirmed by X-ray diffraction analysis, showing I···C contacts between the electropositive σ-hole of the iodine atom and electron-rich πclouds for all crystal structures studied in the solid state.

A case of competitive demethylation by boron tribromide-methyl sulfide complex. A new route to oxazoloquinolines

Reaction of boron tribromide-methyl sulfide complex with 6-methoxy-5- amidoquinolines provides oxazolo(4,5-f) quinolines. In contrast under similar conditions boron tribromide gives only 6-hydroxy-5-amidoquinolines.

Acid-promoted cleavage of the C–C double bond of N-(2-Hydroxylphenyl)enaminones for the synthesis of benzoxazoles

An acid-mediated selective cleavage of C–C double bond of N-(2-hydroxylphenyl)enaminones with formation a new C–O bond for the synthesis of 2-substituted benzoxazoles has been developed. This protocol proceeds under transition metal- and oxidant-free conditions with broad functional group tolerance. The oxidative cleavage of C–C double bond of N-(2-hydroxylphenyl)enaminone is also realized using NCS or NFSI as oxidants with release of 2,2-dihalogen-acetophenone fragments.

Method for synthesizing benzoxazole through microwave radiation of benzamide compound in water phase

The invention discloses a method for synthesizing benzoxazole through microwave radiation of a benzamide compound in a water phase. The benzamide compound is added into the water phase under the microwave condition to be subjected to a cyclization reaction for generating the benzoxazole under the alkali condition, and the method for preparing the benzoxazole is environmentally friendly, easy and convenient to operate, safe, low in cost and efficient. Compared with the prior art, the method can be applied to a large number of functional groups, the yield is high, the number of by-products is small, and the method is easy to operate, safe, low in cost and environmentally friendly. (Please see the specifications for the formula).

Reusable Palladium Nanoparticles Catalyzed Oxime Ether Directed Mono Ortho-Hydroxylation under Phosphine Free Neutral Condition

An efficient, reusable and stable binaphthyl stabilized Pd-nanoparticles (Pd-BNP) catalyzed the direct ortho-C?H hydroxylation of acetophenone oxime ethers under neutral and phosphine ligand-free condition has been developed. A readily available, economic, safe and greener oxidant oxone has been used in this direct ortho-hydroxylation. The scope of the reaction has been studied with various acetophenone oxime ethers including electron rich to electron deficient system and the reaction afforded only mono hydroxylated products in a highly regioselective manner. Several control experiment results confirmed that the oxone is the hydroxyl source. The Pd-BNP catalyst has been reused up to five times. The heterogeneous test confirmed that the reaction is catalyzed by the heterogeneous Pd-BNP catalyst. (Figure presented.).

Eco-friendly syntheses of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives in the presence of imidazolium chloride

A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles and 2-substituted benzothiazoles from 2-aminophenols, 2-aminothiophenols and DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various 2-substituted benzoxazoles and 2-substituted benzothiazoles were thus prepared in moderate to excellent yields.

Synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof

The invention provides a synthesis method of 2-substituted benzoxazole, 2-substituted benzothiazole and derivatives thereof. In the method, through ortho-aminophenol/2-aminothiophenol cyclization catalyzed by imidazole hydrochloride, synthesis of functionalized 2-substituted benzoxazole and 2-substituted benzothiazole is realized; the method is simple, economical and high in practicality. No othercatalysts or additives are used, the synthesis method ensures good functional group tolerance and excellent yield and purity, the reaction time is short, no harsh reaction conditions are needed, andthe method is suitable for industrial production.

Metal free montmorillonite KSF clay catalyzed practical synthesis of benzoxazoles and benzothiazoles under aerobic conditions

An efficient method for the synthesis of benzoxazoles and benzothiazoles via montmorillonite KSF clay catalyzed condensation reaction between 2-aminophenols or 2-aminothiophenols and β-diketones is reported. The efficiency of the reaction reflects from the wide substrate scope with electronic differentiation on aryls. The reaction is metal free and proceeds without the exclusion of air or moisture, and further the catalyst can be recycled up to 3–5 catalytic cycles.

A 2 - substituted benzoxazole derivative of the preparation method

The invention discloses a 2 - substituted benzoxazole derivative of the preparation method, its reaction as follows: . The present invention can be 2 - substituted pyrrole derivatives, acetophenone derivatives can be obtained and at the same time 2, 2 - dihalo acetophenone derivatives; and through the C (sp2 ) - C (sp2 ) At the same time selectively fracture of the aromatization. The method of the invention the resulting raw materials are easy, high yield, mild reaction conditions, the reaction time is short, wide substrate range, reaction specificity is strong, easy post treatment and green environmental protection.