2-Amino-4-bromobenzothiazole

Base Information

• Chemical Name: 2-Amino-4-bromobenzothiazole
• CAS No.: 20358-02-5
• Molecular Formula: C7H5BrN2S
• Molecular Weight: 229.1
• Hs Code.: 29342000
• DSSTox Substance ID: DTXSID10365970
• Nikkaji Number: J182.569K
• Wikidata: Q72438441
• ChEMBL ID: CHEMBL4778811
• Mol file: 20358-02-5.mol

Synonyms:2-Amino-4-bromobenzothiazole;20358-02-5;4-Bromobenzo[d]thiazol-2-amine;4-bromo-1,3-benzothiazol-2-amine;2-AMINO-4-BROMOBENZO[D]THIAZOLE;2-Benzothiazolamine, 4-bromo-;4-bromo-benzothiazol-2-ylamine;4-bromo-2-benzothiazolamine;MFCD04971840;bromo-aminobenzothiazole;SCHEMBL2748892;CHEMBL4778811;DTXSID10365970;2-amino-4-bromo-1,3-benzothiazole;STK729624;AKOS000111677;AM84701;CS-W019966;FS-2058;3-(Acetylaminomethylsulfanyl)propionicacid;AC-26748;SY016639;BB 0246313;FT-0654868;EN300-192678;A814484;J-507835;F1911-0009

Chemical Property of 2-Amino-4-bromobenzothiazole

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Melting Point: 182-184 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.783
• Boiling Point: 366.8 °C at 760 mmHg
• PKA: 2.14±0.10(Predicted)
• Flash Point: 175.7 °C
• PSA: 67.15000
• Density: 1.837 g/cm³
• LogP: 3.22220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 227.93568
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-4-bromobenzo[d]thiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Br)N=C(S2)N

Technology Process of 2-Amino-4-bromobenzothiazole

There total 7 articles about 2-Amino-4-bromobenzothiazole 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: 97.0%

potassium thioacyanate (333-20-0) + 2-bromoaniline (615-36-1) → 4-bromo-1,3-benzothiazol-2-amine (20358-02-5)

Guidance literature:

With sodium iodide dichloride; at 70 ℃; for 0.5h;

DOI:10.1055/s-0032-1317080

Reference yield: 93.0%

1-(2-bromophenyl)thiourea (5391-30-0) → 4-bromo-1,3-benzothiazol-2-amine (20358-02-5)

Guidance literature:

With bromine; In chloroform; at 0 ℃; for 1.5h; Reflux;

DOI:10.1016/j.tet.2020.130982

Reference yield: 77.0%

ammonium thiocyanate + 2-bromoaniline (615-36-1) → 4-bromo-1,3-benzothiazol-2-amine (20358-02-5)

Guidance literature:

ammonium thiocyanate; 2-bromoaniline; With acetic acid; at 10 ℃;

With bromine; at 10 - 20 ℃; for 4h;

DOI:10.1016/j.bmc.2018.02.021

upstream raw materials:

1-(2-bromophenyl)thiourea

2-bromoaniline

o-bromoaniline hydrochloride

potassium thioacyanate

Downstream raw materials:

tert-butyl (4-formylbenzo[d]thiazol-2-yl)carbamate

tert-butyl (4-bromo-1,3-benzothiazol-2-yl)carbamate

2-bromo-6-(methylthio)aniline

Refernces

• 1、 Zhu, Yu-Shen,Shi, Linlin,Fu, Lianrong,Chen, Xiran,Zhu, Xinju,Hao, Xin-Qi,Song, Mao-Ping. "Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles". supporting information. p. 1497 - 1500. Retrieved 2021/09/09.
• 2、 Nguyen, William,Lee, Erinna F.,Evangelista, Marco,Lee, Mihwa,Harris, Tiffany J.,Colman, Peter M.,Smith, Nicholas A.,Williams, Luke B.,Jarman, Kate E.,Lowes, Kym N.,Haeberli, Cécile,Keiser, Jennifer,Smith, Brian J.,Fairlie, W. Douglas,Sleebs, Brad E.. "Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2". . p. 1143 - 1163. Retrieved 2021/02/22.