5-Bromothiazol-2-amine

Base Information

• Chemical Name: 5-Bromothiazol-2-amine
• CAS No.: 3034-22-8
• Molecular Formula: C3H3BrN2S
• Molecular Weight: 179.04
• Hs Code.: 2934100090
• European Community (EC) Number: 924-305-1,819-500-2
• DSSTox Substance ID: DTXSID20275455
• Nikkaji Number: J59.596I
• Mol file: 3034-22-8.mol

Synonyms:3034-22-8;5-bromothiazol-2-amine;2-Amino-5-bromothiazole;5-Bromo-thiazol-2-ylamine;5-Bromo-1,3-thiazol-2-amine;2-Thiazolamine, 5-bromo-;5-bromo-2-Thiazolamine;2-amino-5-bromo-thiazole;MFCD00016893;5-Bromothiazol-2-ylamine;5-Bromo-thiazol-2-ylamine trifluoroacetate;2-Amino-5-bromo-1,3-thiazole;5-bromo-2-aminothiazole;2-Amino-5-Bioomothiazole;2-amino-5 -bromothiazole;2-Amino-5- bromothiazole;5-bromo-thiazole-2-ylamine;5-bromo-thiazol-2-yl-amine;SCHEMBL344676;BDBM25710;DTXSID20275455;5-Bromo-1,3-thiazol-2-amine #;STK400201;AKOS005169841;AM86844;CS-W001219;SY005892;TS-02492;FT-0611153;EN300-33984;A13655;AC-907/25004245;J-640438;W-202251

Chemical Property of 5-Bromothiazol-2-amine

Chemical Property:

• Vapor Pressure: 0.00246mmHg at 25°C
• Melting Point: 165 °C (dec.)(lit.)
• Refractive Index: 1.69
• Boiling Point: 287.6 °C at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 127.7 °C
• PSA: 67.15000
• Density: 1.976 g/cm³
• LogP: 2.06900
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 177.92003
• Heavy Atom Count: 7
• Complexity: 70

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-5-bromothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=N1)N)Br
• General Description: 2-Amino-5-bromothiazole is a key intermediate in the synthesis of 2-amino-5-(thioaryl)thiazoles, which were investigated as potent and selective inhibitors of Itk (Interleukin-2-inducible T cell kinase). It serves as a foundational scaffold in the development of immunosuppressive and anti-inflammatory agents, particularly for modulating T cell activation and allergic responses. The compound's bromo substituent at the 5-position allows for further functionalization, enabling the exploration of structure-activity relationships (SAR) to optimize Itk inhibition and biological activity.

Technology Process of 5-Bromothiazol-2-amine

There total 7 articles about 5-Bromothiazol-2-amine 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: 75.0%

2-thiazolylamine (96-50-4) → 5-bromo-2-aminothiazole (3034-22-8)

Guidance literature:

With bromine; acetic acid; at 0 - 30 ℃; for 2h;

Reference yield: 70.0%

5-bromothiazol-2-amine hydrobromide (61296-22-8) → 5-bromo-2-aminothiazole (3034-22-8)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 4h; Large scale;

Reference yield:

5-bromo-1,3-thiazol-2-amine hydrobromide → 5-bromo-2-aminothiazole (3034-22-8)

Guidance literature:

With sodium carbonate; In water; ethyl acetate;

upstream raw materials:

2-thiazolylamine

2-acetamido-5-bromothiazole

phenyl N-2-(5-bromothiazolyl)carbamate

5-bromothiazol-2-amine hydrobromide

Downstream raw materials:

5-phenylsulfanyl-thiazol-2-ylamine

2-acetamido-5-bromothiazole

N-(5-bromo-thiazol-2-yl)-2-hydroxy-5-nitro-benzamide

N-(5-bromo-thiazol-2-yl)-3,5-dichloro-2-hydroxy-benzamide

Refernces

Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors

10.1016/j.bmcl.2006.04.060

The research presents the discovery and structure-activity relationship (SAR) study of a series of novel 2-amino-5-(thioaryl)thiazoles as potent and selective inhibitors of Itk (Interleukin-2-inducible T cell kinases), an enzyme primarily expressed in T cells and implicated in T cell activation and allergic responses. The study aimed to develop compounds that could serve as immunosuppressive and anti-inflammatory agents. The experiments involved synthesizing a series of aminothiazole-based small molecules and testing their ability to inhibit Itk in vitro and IL-2 secretion in Jurkat T-cell assays. Key reactants included 2-amino-5-bromothiazole, 3-carboxythiophenol, and various amines, with synthesis routes detailed in Schemes 1-3. The analyses used to evaluate the compounds' potency, selectivity, and cell activity included enzyme inhibition assays, cell-based IL-2 secretion assays, and in vivo studies in mice. The research identified compound 3 as a highly potent and selective Itk inhibitor with significant activity in reducing T cell proliferation and IL-2 production, both in vitro and in vivo, including in a mouse model of ovalbumin-induced allergy/asthma.