Methyl benzo[d]oxazole-2-carboxylate

Base Information

• Chemical Name: Methyl benzo[d]oxazole-2-carboxylate
• CAS No.: 27383-86-4
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.15700
• Hs Code.: 2934999090
• European Community (EC) Number: 968-776-1
• DSSTox Substance ID: DTXSID40538014
• Nikkaji Number: J2.867.043E
• Wikidata: Q82413217
• Mol file: 27383-86-4.mol

Synonyms:Methyl benzo[d]oxazole-2-carboxylate;27383-86-4;Benzooxazole-2-carboxylic acid methyl ester;Methyl 1,3-benzoxazole-2-carboxylate;METHYL BENZOOXAZOLE-2-CARBOXYLATE;methyl benzoxazole-2-carboxylate;Methylbenzo[d]oxazole-2-carboxylate;Neopentylglycoldiacrylate;SCHEMBL212819;Methyl 2-benzoxazolecarboxylate;DTXSID40538014;YDKNBNOOCSNPNS-UHFFFAOYSA-N;MFCD09701312;AKOS002659346;SB36331;DS-11438;CS-0061868;EN300-1696972;A848762;Z1198221054

Chemical Property of Methyl benzo[d]oxazole-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00614mmHg at 25°C
• Melting Point: 99 °C
• Boiling Point: 272.3oC at 760 mmHg
• PKA: 0.14±0.10(Predicted)
• Flash Point: 118.5oC
• PSA: 52.33000
• Density: 1.288g/cm3
• LogP: 1.61440
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

99% ^*data from raw suppliers

MethylBenzo[D]oxazole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=NC2=CC=CC=C2O1
• Uses: Methyl Benzo[D]oxazole-2-carboxylate is used as a reactant in the preparation of benzoxazole-based oxadiazoles as antimicrobial agents.

Technology Process of Methyl benzo[d]oxazole-2-carboxylate

There total 17 articles about Methyl benzo[d]oxazole-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.2%

benzoxazole (273-53-0,29791-96-6) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → benzoxazole-2-carboxylic acid methyl ester (27383-86-4)

Guidance literature:

benzoxazole; carbon dioxide; With Mo₂(O-t-Bu)6; caesium carbonate; In N,N-dimethyl-formamide; at 75 ℃; for 10h; under 760.051 Torr; Schlenk technique;

methyl iodide; In N,N-dimethyl-formamide; at 50 ℃; for 2h; Schlenk technique;

DOI:10.1039/c7gc03372a

Reference yield: 76.0%

methanol (67-56-1) + benzo[d]oxazole-2-carbonyl chloride (408538-63-6) → benzoxazole-2-carboxylic acid methyl ester (27383-86-4)

Guidance literature:

With triethylamine; for 3h; Reflux;

DOI:10.1016/j.cclet.2013.04.005

Reference yield: 71.0%

N-2-hydroxyphenylglycine methyl ester → benzoxazole-2-carboxylic acid methyl ester (27383-86-4)

Guidance literature:

With copper(l) iodide; C₃₀H₂₄N₆Ru⁽²⁺⁾*2Cl^(1-)*66H₂O; In acetonitrile; at 20 ℃; for 12h;

upstream raw materials:

methyl 2-benzoxazolimidate

methyl 2,2,2-trimethoxyacetate

2-amino-phenol

2-chloro-1,3-benzoxazole

Downstream raw materials:

benzooxazole-2-carboxylic acid 3-chloro-anilide

3-(3-chloro-anilino)-benzo[1,4]oxazin-2-one

benzooxazole-2-carboxylic acid 3,4-dichloro-anilide

3-(3,4-dichloro-anilino)-benzo[1,4]oxazin-2-one

Refernces

• 1、 Lee, Mijung,Hwang, Young Kyu,Kwak, Jaesung. "Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives". . p. 3136 - 3144. Retrieved 2021/09/30.
• 2、 Liu, Shan,Zhu, Zhi-Qiang,Hu, Zhi-Yu,Tang, Juan,Yuan, En. "Copper-catalyzed oxidative cyclization of glycine derivatives toward 2-substituted benzoxazoles". supporting information. p. 1616 - 1619. Retrieved 2021/03/01.