4-Thiazolecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-Thiazolecarboxylic acid tert-butyl ester
• CAS No.: 1037746-91-0
• Molecular Formula: C8H11NO2S
• Molecular Weight: 185.247
• Mol file: 1037746-91-0.mol

Synonyms:4-Thiazolecarboxylic acid tert-butyl ester

Chemical Property of 4-Thiazolecarboxylic acid tert-butyl ester

Chemical Property:

• Melting Point: 81-82 °C
• Boiling Point: 254.5±13.0 °C(Predicted)
• PKA: 0.19±0.10(Predicted)
• PSA: 67.43000
• Density: 1.160±0.06 g/cm3(Predicted)
• LogP: 2.09840

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thiazolecarboxylic acid tert-butyl ester

There total 1 articles about 4-Thiazolecarboxylic acid tert-butyl ester 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: 94.0%

Thiazole-4-carboxylic acid (3973-08-8) + tert-butyl alcohol (75-65-0) → tert-butyl 1,3-thiazole-4-carboxylate (1037746-91-0)

Guidance literature:

Thiazole-4-carboxylic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

tert-butyl alcohol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 60 ℃; for 48h;

DOI:10.1021/ol801035c

Reference yield: 91.0%

bromobenzene (108-86-1,52753-63-6) + tert-butyl 1,3-thiazole-4-carboxylate (1037746-91-0) → tert-butyl 2-phenylthiazole-4-carboxylate (1037746-97-6)

Guidance literature:

With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 18h; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.tet.2013.01.073

Reference yield: 81.0%

iodobenzene (591-50-4) + tert-butyl 1,3-thiazole-4-carboxylate (1037746-91-0) → tert-butyl 2-phenylthiazole-4-carboxylate (1037746-97-6)

Guidance literature:

With palladium diacetate; caesium carbonate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 110 ℃; for 18h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/ol801035c

upstream raw materials:

Thiazole-4-carboxylic acid

tert-butyl alcohol

Downstream raw materials:

tert-butyl 2-(4-nitrophenyl)thiazole-4-carboxylate

tert-butyl 2-phenylthiazole-4-carboxylate

tert-butyl 2-(4-methoxyphenyl)thiazole-4-carboxylate

2-(4-cyano-phenyl)-thiazole-4-carboxylic acid tert-butyl ester

Refernces

• 1、 Martin, Thibaut,Verrier, Cecile,Hoarau, Christophe,Marsais, Francis. "Direct C-2 arylation of alkyl 4-thiazolecarboxylates: New insights in synthesis of heterocyclic core of thiopeptide antibiotics". supporting information; experimental part. p. 2909 - 2912. Retrieved 2009/05/30.