4-Bromo-2-isopropylthiazole

Base Information

• Chemical Name: 4-Bromo-2-isopropylthiazole
• CAS No.: 376585-97-6
• Molecular Formula: C6H8BrNS
• Molecular Weight: 206.1
• Hs Code.: 2934100090
• European Community (EC) Number: 641-173-8
• DSSTox Substance ID: DTXSID20376794
• Nikkaji Number: J1.598.421J
• Wikidata: Q82165713
• Mol file: 376585-97-6.mol

Synonyms:4-Bromo-2-isopropylthiazole;376585-97-6;4-bromo-2-isopropyl-1,3-thiazole;4-bromo-2-propan-2-yl-1,3-thiazole;Thiazole, 4-bromo-2-(1-methylethyl)-;2-Isopropyl-4-bromothiazole;SCHEMBL3959367;4-bromo-2-(iso-propyl)thiazole;DTXSID20376794;MIHUGKROHGQVQY-UHFFFAOYSA-N;BQA58597;MFCD06660118;AKOS015834964;CS-W001553;MB04003;s11446;BS-28174;FT-0685140;EN300-1077114;4-BROMO-2-(PROPAN-2-YL)-1,3-THIAZOLE;A874043;J-514662

Chemical Property of 4-Bromo-2-isopropylthiazole

Chemical Property:

• Vapor Pressure: 0.19mmHg at 25°C
• Boiling Point: 218°C at 760 mmHg
• Flash Point: 85.7°C
• PSA: 41.13000
• Density: 1.489g/cm³
• LogP: 3.02900
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 204.95608
• Heavy Atom Count: 9
• Complexity: 97.1

Purity/Quality:

98%min ^*data from raw suppliers

4-Bromo-2-isopropylthiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=NC(=CS1)Br

Technology Process of 4-Bromo-2-isopropylthiazole

There total 2 articles about 4-Bromo-2-isopropylthiazole 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: 72.0%

iso-propylzinc chloride (38111-45-4) + 2,4-dibromo-1,3-thiazole (4175-77-3) → 4-bromo-2-(propan-2-yl)-1,3-thiazole (376585-97-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/ejoc.200800203

Reference yield: 72.0%

isopropyllithium (1888-75-1) + 2,4-dibromo-1,3-thiazole (4175-77-3) → 4-bromo-2-(propan-2-yl)-1,3-thiazole (376585-97-6)

Guidance literature:

isopropyllithium; With zinc(II) chloride; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 0.5h;

2,4-dibromo-1,3-thiazole; With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; pentane; at 20 ℃; for 16h; Further stages.;

DOI:10.1021/jo025661o

Reference yield: 32.0%

3-fluoro-4-formylphenylboronic acid (248270-25-9) + 4-bromo-2-(propan-2-yl)-1,3-thiazole (376585-97-6) → 2-fluoro-4-(2-isopropylthiazol-4-yl)benzaldehyde (1240321-56-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,2-dimethoxyethane; water; at 150 ℃; for 2h; Sealed tube;

DOI:10.1021/jm1002414

upstream raw materials:

iso-propylzinc chloride

2,4-dibromo-1,3-thiazole

isopropyllithium

Downstream raw materials:

2-fluoro-4-(2-isopropylthiazol-4-yl)benzaldehyde

Refernces

• 1、 Gross, Stefan,Heuser, Stefan,Ammer, Carolin,Heckmann, Golo,Bach, Thorsten. "2,4-Disubstituted thiazoles by regioselective cross-coupling or bromine-magnesium exchange reactions of 2,4-dibromothiazole". experimental part. p. 199 - 206. Retrieved 2011/03/18.
• 2、 Bach, Thorsten,Heuser, Stefan. "Regioselective cross-coupling reactions as an entry into biologically relevant bithiazoles: First total synthesis of cystothiazole E". . p. 3184 - 3185. Retrieved 2007/10/03.