Methyl 2-bromomethyl-4-oxazolecarboxylate

Base Information

• Chemical Name: Methyl 2-bromomethyl-4-oxazolecarboxylate
• CAS No.: 175551-77-6
• Molecular Formula: C6H6 Br N O3
• Molecular Weight: 220.023
• Hs Code.: 2934999090
• European Community (EC) Number: 801-853-9
• DSSTox Substance ID: DTXSID00449677
• Wikidata: Q72488735
• Mol file: 175551-77-6.mol

Synonyms:175551-77-6;Methyl 2-bromomethyl-4-oxazolecarboxylate;methyl 2-(bromomethyl)oxazole-4-carboxylate;Methyl 2-(bromomethyl)-1,3-oxazole-4-carboxylate;4-Oxazolecarboxylic acid, 2-(bromomethyl)-, methyl ester;SCHEMBL346006;DTXSID00449677;MFCD08166584;AKOS015909137;CS-W004407;AMY202100041;A3899;FT-0650628;D77664;METHYL2-BROMOMETHYL-4-OXAZOLECARBOXYLATE

Chemical Property of Methyl 2-bromomethyl-4-oxazolecarboxylate

Chemical Property:

• Vapor Pressure: 0.029mmHg at 25°C
• Melting Point: 49-51℃
• Refractive Index: 1.53
• Boiling Point: 245.1°Cat760mmHg
• Flash Point: 102°C
• PSA: 52.33000
• Density: 1.656g/cm³
• LogP: 1.35610
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 218.95311
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-(bromomethyl)oxazole-4-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(=N1)CBr

Technology Process of Methyl 2-bromomethyl-4-oxazolecarboxylate

There total 6 articles about Methyl 2-bromomethyl-4-oxazolecarboxylate 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: 62.0%

2-methyl-oxazole-4-carboxylic acid methyl ester (85806-67-3) → methyl 2-(bromomethyl)oxazole-4-carboxylate (175551-77-6)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane;

DOI:10.15227/orgsyn.079.0244

Reference yield: 34.0%

2-methyl-oxazole-4-carboxylic acid methyl ester (85806-67-3) → methyl 2-(bromomethyl)oxazole-4-carboxylate (175551-77-6) + 2-dibromomethyl-oxazole-4-carboxylic acid methyl ester

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 1.5h; Irradiation;

DOI:10.1021/jm020881f

Reference yield:

t-butyl 2-(bromomethyl)oxazole-4-carboxylate (87027-39-2) → methyl 2-(bromomethyl)oxazole-4-carboxylate (175551-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA

With trifluoroacetic acid;

DOI:10.1021/ja954311z

upstream raw materials:

diazomethane

2-methyl-oxazole-4-carboxylic acid methyl ester

t-butyl 2-(bromomethyl)oxazole-4-carboxylate

Downstream raw materials:

(12E,17E,19E)-(7R,10R,11R,21S)-21-(tert-Butyl-diphenyl-silanyloxy)-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triaza-tricyclo[23.2.1.0^3,7]octacosa-1⁽²⁷⁾,12,17,19,25⁽²⁸⁾-pentaene-2,8,14,23-tetraone

virginiamycin M2

(R)-((3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(chloromethyl)-oxazole-4-carbonyl)pyrrolidine-2-carboxylate

(R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester

Refernces

• 1、 Schaeckel, Romy,Hinkelmann, Bettina,Sasse, Florenz,Kaiesse, Markus. "The synthesis of novel disorazoles". supporting information; experimental part. p. 1619 - 1622. Retrieved 2010/06/16.
• 2、 White, James D.,Kranemann, Christian L.,Kuntiyong, Punlop,Kitamura, Mitsuru,Narasaka, Koichi. "4-Methoxycarbonyl-2-methyl-1,3-oxazole: [4-oxazolecarboxylic acid, 2-methyl-, methyl ester]". . p. 244 - 244. Retrieved 2017/09/16.