6-Cyanobenzothiazole

Base Information

• Chemical Name: 6-Cyanobenzothiazole
• CAS No.: 58249-61-9
• Molecular Formula: C8H4N2S
• Molecular Weight: 160.199
• Hs Code.: 2934999090
• European Community (EC) Number: 886-262-4
• DSSTox Substance ID: DTXSID30442358
• Nikkaji Number: J984.591G
• Wikidata: Q82259592
• Mol file: 58249-61-9.mol

Synonyms:6-Cyanobenzothiazole;58249-61-9;1,3-benzothiazole-6-carbonitrile;benzo[d]thiazole-6-carbonitrile;Benzothiazole-6-carbonitrile;6-BENZOTHIAZOLECARBONITRILE;6-cyanobenzothiazol;6-cyanobenzthiazole;SCHEMBL1799071;DTXSID30442358;WYRRTJKOMZONQO-UHFFFAOYSA-N;MFCD06659656;AKOS006282132;AB26026;DS-0668;FS-2929;FT-0758592;VU0549436-1;EN300-101213;A869494;J-518671;F9995-1163

Chemical Property of 6-Cyanobenzothiazole

Chemical Property:

• Melting Point: 137-138℃
• Boiling Point: 321.4±15.0 °C(Predicted)
• PKA: -0.99±0.10(Predicted)
• PSA: 64.92000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 2.16798
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 160.00951931
• Heavy Atom Count: 11
• Complexity: 196

Purity/Quality:

98%min ^*data from raw suppliers

6-Cyanobenzothiazol ^*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
• Uses: 6-Cyanobenzothiazol is a useful reagent in preparation of heteroaryl carboxylic acids and esters via carboxylation of oxazoles, thiazoles and oxadiazoles.

Technology Process of 6-Cyanobenzothiazole

There total 9 articles about 6-Cyanobenzothiazole 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: 99.0%

zinc(II) cyanide (557-21-1) + 6-bromo-1,3-benzothiazole (53218-26-1) → 6-cyano benzothiazole (58249-61-9)

Guidance literature:

With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate; In tetrahydrofuran; water; at 40 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol5032359

Reference yield: 95.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + 4-amino-3-iodobenzonitrile (33348-34-4) → 6-cyano benzothiazole (58249-61-9)

Guidance literature:

With copper(l) iodide; potassium sulfide; ammonium acetate; water; at 140 ℃; for 10h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.0c00994

Reference yield: 93.0%

→ 6-cyano benzothiazole (58249-61-9)

Guidance literature:

With water; caesium carbonate; for 0.166667h; Microwave irradiation;

upstream raw materials:

2-amino-6-cyanobenzthiazole

acrylonitrile

4,5-bis(dibromomethyl)thiazole

4-Aminobenzonitrile

Downstream raw materials:

benzothiazole-6-carboxylic acid

4-amino-3-mercaptobenzonitrile

2-phenylbenzo[d]thiazole-6-carbonitrile

2-amino-6-cyanobenzthiazole

Refernces

• 1、 -. "Synthetic method of ammonium acetate-mediated benzothiazole compound". Paragraph 0042-0044. . Retrieved 2020/11/23.
• 2、 Cohen, Daniel T.,Buchwald, Stephen L.. "Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media". supporting information. p. 202 - 205. Retrieved 2015/01/30.