2-Aminobenzothiazole-6-carbonitrile

Base Information

• Chemical Name: 2-Aminobenzothiazole-6-carbonitrile
• CAS No.: 19759-66-1
• Molecular Formula: C8H5 N3 S
• Molecular Weight: 175.214
• Hs Code.: 2934200090
• European Community (EC) Number: 678-674-6
• DSSTox Substance ID: DTXSID80401970
• Nikkaji Number: J40.180C
• Wikidata: Q72438069
• ChEMBL ID: CHEMBL330477
• Mol file: 19759-66-1.mol

Synonyms:19759-66-1;2-aminobenzothiazole-6-carbonitrile;2-Amino-benzothiazole-6-carbonitrile;2-aminobenzo[d]thiazole-6-carbonitrile;2-amino-1,3-benzothiazole-6-carbonitrile;6-Benzothiazolecarbonitrile, 2-amino-;MFCD02664359;2-amino-6-cyanobenzothiazole;CHEMBL330477;SCHEMBL2001976;DTXSID80401970;GDFCZZHSWGWCHP-UHFFFAOYSA-N;BCP26481;BBL029734;STK946228;AKOS005642520;AS-5421;CS-W021580;AC-27163;SY102284;AM20030277;FT-0649691;EN300-249991;J-508026;F2169-0130;InChI=1/C8H5N3S/c9-4-5-1-2-6-7(3-5)12-8(10)11-6/h1-3H,(H2,10,11

Chemical Property of 2-Aminobenzothiazole-6-carbonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 216-218 °C(Solv: ethanol (64-17-5))
• Boiling Point: 399.69°C at 760 mmHg
• PKA: 2.10±0.10(Predicted)
• Flash Point: 195.525°C
• PSA: 90.94000
• Density: 1.452g/cm³
• LogP: 2.33138
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 175.02041835
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

2-Aminobenzothiazole-6-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C#N)SC(=N2)N

Technology Process of 2-Aminobenzothiazole-6-carbonitrile

There total 11 articles about 2-Aminobenzothiazole-6-carbonitrile 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: 95.0%

ammonium thiocyanate + 4-Aminobenzonitrile (873-74-5) → 2-amino-6-cyanobenzthiazole (19759-66-1)

Guidance literature:

With N,N,N-trimethylbenzenemethanaminium dichloroiodate; In water; dimethyl sulfoxide; at 70 ℃; for 1h;

DOI:10.1016/j.tetlet.2021.153388

Reference yield: 91.0%

6-cyano benzothiazole (58249-61-9) + potassium selenocyanate (3425-46-5) → 2-amino-6-cyanobenzthiazole (19759-66-1)

Guidance literature:

With trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; iodine; In water; at 110 ℃; for 6h; Sealed tube; Green chemistry;

DOI:10.1016/j.cclet.2021.08.070

Reference yield: 82.0%

ammonium thiocyanate (1147550-11-5) + 4-Aminobenzonitrile (873-74-5) → 2-amino-6-cyanobenzthiazole (19759-66-1)

Guidance literature:

With bromine; acetic acid; at 20 ℃; for 3h;

upstream raw materials:

4-cyanophenylthiourea

sodium thiocyanide

4-Aminobenzonitrile

potassium thioacyanate

Downstream raw materials:

2-Guanidino-thiazole-4-carboxylic acid (6-cyano-benzothiazol-2-yl)-amide; hydrochloride

6-cyano benzothiazole

4-amino-3-mercaptobenzoic acid

N-(6-cyanobenzo[d]thiazol-2-yl)-1H-imidazole-1-carboxamide

Refernces

• 1、 Chen, Xiran,Fu, Lianrong,Hao, Xin-Qi,Shi, Linlin,Song, Mao-Ping,Zhu, Xinju,Zhu, Yu-Shen. "Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles". supporting information. . Retrieved 2021/09/09.
• 2、 Aitken, Laura,Benek, Ondrej,Chribek, Matej,Dolezal, Rafael,Gunn-Moore, Frank,Hrabinova, Martina,Hroch, Lukas,Jun, Daniel,Kralova, Vendula,Kuca, Kamil,Lycka, Antonin,Musilek, Kamil,Prchal, Lukas,Schmidt, Monika,Vinklarova, Lucie,Zemanova, Lucie. "Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment". . . Retrieved 2020/03/26.