7724-12-1

Basic information

• Product Name: 6-Amino-2-benzothiazolecarbonitrile
• Synonyms: 6-AMINO-2-BENZOTHIAZOLECARBONITRILE;2-Cyano-6-aminobenzothiazole;6-amino-1,3-benzothiazole-2-carbonitrile;2-Cyano-6-aminobenzothiazole, 6-Amino-2-benzothiazolecarbonitrile;6-Amino-2-cyanobenzothiazole;6-Amino-2-cyanobenzothiazole 97%;2-Cyano-6-aminobenzothiazole, >=98%;2-Benzothiazolecarbonitrile,6-amino-(7CI,9CI)
• CAS NO: 7724-12-1
• Molecular Formula: C₈H₅N₃S
• Molecular Weight: 175.21
• Product Categories: BENZOTHIAZOLE
• Mol File: 7724-12-1.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 384.914 °C at 760 mmHg
• Flash Point: 186.59 °C
• Appearance: /
• Density: 1.45
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.736
• Storage Temp.: 2-8°C
• PKA: 1.43±0.10(Predicted)
• BRN: 1567902
• CAS DataBase Reference: 6-Amino-2-benzothiazolecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Amino-2-benzothiazolecarbonitrile(7724-12-1)
• EPA Substance Registry System: 6-Amino-2-benzothiazolecarbonitrile(7724-12-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 7724-12-1(Hazardous Substances Data)

Usage

General Description

6-Amino-2-benzothiazolecarbonitrile is a chemical compound with the molecular formula C8H6N4S. It is a benzothiazole derivative, specifically an aminobenzothiazolecarbonitrile, and is commonly used in the synthesis of pharmaceuticals and agrochemicals. 6-Amino-2-benzothiazolecarbonitrile has a variety of applications, including as an intermediate in the production of dyes and pigments, as well as in the manufacturing of rubber chemicals and antioxidants. It is also used in the synthesis of biologically active compounds, making it an important building block for pharmaceutical research and development. Additionally, 6-Amino-2-benzothiazolecarbonitrile may have potential uses in other areas, such as material science and organic synthesis.

InChI:InChI=1/C8H5N3S/c9-4-8-11-6-2-1-5(10)3-7(6)12-8/h1-3H,10H2

Upstream product

• 2406-90-8 2-chlorobenzothiazol-6-ylamine 
• 151-50-8 potassium cyanide 
• 1422655-40-0 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl (2-cyanobenzo[d]thiazol-6-yl)carbamate 
• 75318-48-8 N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-nitrobenzenamine 
• 100-01-6 4-nitro-aniline 
• 23451-98-1 2-amino-5-nitrobenzenethiol 
• 4953-70-2 N-(p-Nitrophenyl)cyanothioformamide 
• 188672-83-5 6-nitro-1,3-benzothiazole-2-carbonitrile 
• 2407-11-6 2-chloro-6-nitrobenzothiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 29198-43-4 benzothiazole-2-amide 
• 2602-85-9 benzothiazole-2-carbonitrile 
• 32137-76-1 benzothiazole-2-carboxylic acid ethyl ester 
• 2942-06-5 6-nitrobenzo[d]thiazole 

Downstream Products

• 934270-90-3 6-(3-phenylpropylamino)-2-cyanobenzothiazole 
• 1318692-71-5 6-(4-phenylbutylamino)-2-cyanobenzothiazole 
• 934270-89-0 6-phenethylamino-2-cyanobenzothiazole 
• 934270-88-9 6-benzylamino-2-cyanobenzothiazole 
• 1318692-88-4 6-[6-(benzyloxycarbonylamino)hexylamino]-2-cyanobenzothiazole 
• 1422655-40-0 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl (2-cyanobenzo[d]thiazol-6-yl)carbamate 
• 1476735-93-9 4-((2-cyanobenzo[d]thiazol-6-ylcarbamoyloxy)methyl)phenylboronic acid 

Relevant articles and documents

Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin

All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.

NOVEL CHEMILUMINESCENT SUBSTRATES FOR FACTOR XA

The present invention relates to chemiluminescent substrates of formulas (I-3) and (I-4) for blood clotting enzyme Factor Xa. The substrates are particularly useful for assaying coagulation factors and for quantifying an anticoagulant in a sample.

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT), which has an amine handle for straight-forward derivatisation. Here we present an economical and scalable synthesis of ACBT based on a cyanation catalysed by 1,4-diazabicyclo[2.2.2]octane (DABCO), and discuss its advantages for scale-up over previously reported routes.