103965-99-7

Basic information

• Product Name: 4-(2-Bromo-phenyl)-thiazol-2-ylamine
• Synonyms: 2-AMino-4-(2-broMophenyl)thiazole;4-(2-Bromophenyl)thiazol-2-amine
• CAS NO: 103965-99-7
• Molecular Formula: C₉H₇BrN₂S
• Molecular Weight: 255.13
• Mol File: 103965-99-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 123 °C(Solv: ethanol (64-17-5))
• Boiling Point: 395.1±17.0 °C(Predicted)
• Appearance: /
• Density: 1.636±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.73±0.10(Predicted)
• CAS DataBase Reference: 4-(2-Bromo-phenyl)-thiazol-2-ylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Bromo-phenyl)-thiazol-2-ylamine(103965-99-7)
• EPA Substance Registry System: 4-(2-Bromo-phenyl)-thiazol-2-ylamine(103965-99-7)

Safety Data

• Hazardous Substances Data: 103965-99-7(Hazardous Substances Data)

Usage

Uses

2-Amino-4-(2-bromophenyl)thiazole is a useful intermediate for the synthesis and screening of 2-aminothiazoles as antimicrobials focusing on MRSA.

Upstream product

• 1073483-44-9 1-(1-azidovinyl)-2-bromobenzene 
• 333-20-0 potassium thioacyanate 
• 2142-69-0 2-bromophenyl methyl ketone 
• 49851-55-0 2,2'-dibromoacetophenone 
• 17356-08-0 thiourea 
• 2039-88-5 2-bromostyrene 

Downstream Products

• 103966-07-0 2-p-chlorobenzoylamino-4-o-bromophenylthiazole 
• 1415695-81-6 C₁₆H₁₁F₃N₂OS 
• 1415695-79-2 C₁₅H₁₁BrN₂O₂S₂ 
• 103966-21-8 1-(4-o-bromophenylthiazol-2-yl)-5-p-methoxyphenyltetrazole 
• 103966-22-9 1-(4-o-bromophenylthiazol-2-yl)-5-p-chlorophenyltetrazole 
• 103966-28-5 2-p-methoxyphenyl-5-o-bromophenylthiazolo<3,2-b>-s-triazole 
• 103966-20-7 1-(4-o-bromophenylthiazol-2-yl)-5-phenyltetrazole 
• 103966-29-6 2-p-chlorophenyl-5-o-bromophenylthiazolo<3,2-b>-s-triazole 
• 103966-27-4 2-phenyl-5-o-bromophenylthiazolo<3,2-b>-s-triazole 
• 103966-06-9 2-p-methoxybenzoylamino-4-o-bromophenylthiazole 
• 103966-05-8 2-benzamido-4-o-bromophenylthiazole 

Relevant articles and documents

Selective Access to 4-Substituted 2-Aminothiazoles and 4-Substituted 5-Thiocyano-2-aminothiazoles from Vinyl Azides and Potassium Thiocyanate Switched by Palladium and Iron Catalysts

A highly selective construction of 4-substituted 2-aminothiazoles and 4-substituted 5-thiocyano-2-aminothiazoles, respectively, catalyzed by palladium(II) acetate and promoted by iron(III) bromide from vinyl azides and potassium thiocyanate has been developed. Use of readily available starting materials, high selectivity, as well as mild reaction conditions make this practical method particularly attractive.

Synthesis and spectroscopic studies of new schiff bases

Five novel Schiff bases have been prepared from o-formylphenoxyacetic acid and a series of aminothiazoles to form a number of potentially biologically active compounds. The structures of these Schiff bases have been characterized using IR and 1

A one-pot synthesis of 2-aminothiazoles via the coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system

A series of 2-aminothiazoles is prepared in moderate-to-good yields by the direct coupling of ketones and thiourea using I2/dimethyl sulfoxide as a catalytic oxidative system. This method avoids the preparation of lachrymatory and toxic α-haloketones and the use of an acid-binding agent, thus providing a more convenient approach to 2-aminothiazoles compared to the Hantzsch reaction.

Development of 2-amino-4-phenylthiazole analogues to disrupt myeloid differentiation factor 88 and prevent inflammatory responses in acute lung injury

Myeloid differentiation primary response protein 88 (MyD88), an essential adapter protein used by toll-like receptors (TLR), is a promising target molecule for the treatment of respiratory inflammatory diseases. Previous studies explored the activities of novel 2-amino-4-phenylthiazole analogue (6) in inflammation-induced cancer, and identified the analogue as an inhibitor of MyD88 toll/interleukin-1 receptor (TIR) homology domain dimerization. Here, we describe the synthesis of 47 new analogues by modifying different sites on this lead compound and assessed their anti-inflammatory activities in lipopolysaccharide-induced mouse primary peritoneal macrophages (MPMs). The most promising compound, 15d, was found to effectively interact with MyD88 protein and prevented formation of the MyD88 homodimeric complex. Furthermore, 15d showed in vivo anti-inflammatory activity in LPS-caused model of acute lung injury. This work provides new candidates as MyD88 inhibitors to combat inflammation diseases.

Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

An efficient procedure for the synthesis of 2-aminothiazoles via DBH-mediated oxidative cyclization of styrenes and thioureas is reported. Various alkenes were successfully transformed to the corresponding 2-aminothiazoles in yields of 10–81% via a two-step one-pot manner using DBH as both the bromine source and oxidant. The method can be readily carried out in gram-scale and successfully applied to the synthesis of anti-inflammatory drug fanetizole using styrene as starting material.