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

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

Used in Pharmaceutical Industry:
4-(2-Bromo-phenyl)-thiazol-2-ylamine is used as a key intermediate in the synthesis of 2-aminothiazoles, which are known for their antimicrobial properties. Specifically, these compounds are utilized in the development of drugs targeting Methicillin-resistant Staphylococcus aureus (MRSA), a significant concern in healthcare settings due to its resistance to many commonly used antibiotics.
In the context of antimicrobial drug development, 4-(2-Bromo-phenyl)-thiazol-2-ylamine serves as a building block for creating novel 2-aminothiazole derivatives with enhanced activity against MRSA. The presence of the bromine atom on the phenyl ring allows for further functionalization and optimization of the molecule's biological activity, potentially leading to the discovery of new and effective treatments against resistant bacterial strains.

Upstream product

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

Downstream Products

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

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 antibacterial activity of bis[2-amino-4-phenyl-5-thiazolyl] disulfides

Different dimeric disulfides, having the basic skeleton of bis[2-amino-4-phenyl-5-thiazolyl] disulfides were synthesized in a straightforward manner from acetophenones. 2-Amino-4-phenyl-1,3-thiazoles were prepared by the reaction of thiourea with substitu

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

Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach

An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.

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.

Method for preparing 2-aminothiazole compound

The invention discloses a method for preparing a 2-aminothiazole compound. The method comprises the following steps: in an organic solvent, carrying out a condensation reaction on thiourea representedby a formula (II) and a ketone compound represented by a formula (III) at 50-120 DEG C for 6-24 h under the catalysis of elemental iodine, and after the reaction is finished, carrying out post-treatment on the reaction solution to obtain the 2-aminothiazole compound represented by a formula (I). According to the invention, the method has characteristics of cheap and easily available reaction rawmaterials, mild reaction conditions, simpleness, no requirement of transition metal catalysts and a stoichiometric halogenating reagents and cost reducing, and can be used for synthesizing a series of2-aminothiazole derivatives, and the prepared products can be used as important intermediates for synthesizing thiazole structure-containing drugs or bioactive compounds.

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.

SUBSTITUTED AMINOTHIAZOLES AS INHIBITORS OF NUCLEASES

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3, R4, R5, R6 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated 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.

4 - substituted -2 - amino thiazole compound preparation method

The invention discloses a preparation method of a 4-substituted-2-aminothiazole compound. The method comprises the following step: olefin azide shown by the formula I reacts with potassium thiocyanate under the catalysis of palladium acetate to obtain the 4-substituted-2-aminothiazole compound, wherein the molar ratio of the olefin azide compound to potassium thiocyanate to palladium acetate is 20:(59-61):1, the reaction temperature is 75-85 DEG C, and the reaction time is 11-13 hours; and in the formula I, R1 is phenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-methylphenyl, 4-ethyoxy-3-bromophenyl, 3-nitrophenyl, 4-methoxyacylphenyl, 1-naphthyl, phenylaminomethyl or trans-4-(3-phenylallyloxymethyl).