tert-butyl 2-bromothiazol-5-ylcarbamate

Base Information

• Chemical Name: tert-butyl 2-bromothiazol-5-ylcarbamate
• CAS No.: 1094070-77-5
• Molecular Formula: C8H11BrN2O2S
• Molecular Weight: 279.158
• Hs Code.: 2934100090
• Mol file: 1094070-77-5.mol

Synonyms:Urethane

Chemical Property of tert-butyl 2-bromothiazol-5-ylcarbamate

Chemical Property:

• Appearance/Colour: White to off-white powder
• Boiling Point: 294℃
• PKA: 11.83±0.70(Predicted)
• Flash Point: 131℃
• PSA: 79.46000
• Density: 1.574
• LogP: 3.32560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl(2-Bromothiazol-5-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl (2-bromothiazol-5-yl)carbamate is a useful reactant for the synthesis of imidazo[1,2-a]pyrazine deratives, which could act as Aurora kinase inhibitors.

Technology Process of tert-butyl 2-bromothiazol-5-ylcarbamate

There total 4 articles about tert-butyl 2-bromothiazol-5-ylcarbamate 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: 77.0%

2-bromo-1,3-thiazole (3034-53-5,215777-74-5) + N-chloro-N-sodio-tert-butylcarbamate (73210-14-7) → (2-bromo-thiazol-5-yl)-carbamic acid tert-butyl ester (1094070-77-5)

Guidance literature:

With [Cu(1,3-di-iso-propylimidazolin-2-ylidene)(Cl)]; sodium t-butanolate; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jacs.6b07486

Reference yield: 66.0%

2-bromo-thiazole-5-carboxylic acid (54045-76-0) + tert-butyl alcohol (75-65-0) → (2-bromo-thiazol-5-yl)-carbamic acid tert-butyl ester (1094070-77-5)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; at 80 ℃; for 10h;

Reference yield:

tert-butyl carbazate (4248-19-5) → (2-bromo-thiazol-5-yl)-carbamic acid tert-butyl ester (1094070-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: trichloroisocyanuric acid / methanol / 1 h / 20 °C

2: sodium hydroxide / methanol / 0.5 h / 0 - 20 °C

3: [Cu(1,3-di-iso-propylimidazolin-2-ylidene)(Cl)]; sodium t-butanolate / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere

With trichloroisocyanuric acid; [Cu(1,3-di-iso-propylimidazolin-2-ylidene)(Cl)]; sodium hydroxide; sodium t-butanolate; In tetrahydrofuran; methanol;

DOI:10.1021/jacs.6b07486

upstream raw materials:

2-bromo-thiazole-5-carboxylic acid

tert-butyl alcohol

2-bromo-1,3-thiazole

N-chloro-N-sodio-tert-butylcarbamate

Downstream raw materials:

1,1-dimethylethyl (2-bromo-1,3-thiazol-5-yl)((2S)-2-((((1,1-dimethylethyl)oxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propyl)-carbamate

Refernces

• 1、 -. "ANTI-HUMAN VISTA ANTIBODIES AND USE THEREOF". Paragraph 442; 507. . Retrieved 2021/10/30.
• 2、 -. "PESTICIDAL METHODS USING SUBSTITUTED 3-PYRIDYL THIAZOLE COMPOUNDS AND DERIVATIVES FOR COMBATING ANIMAL PESTS". Page/Page column 94; 95. . Retrieved 2014/01/08.