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

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

Uses

Used in Pharmaceutical and Agrochemical Industries:
6-Amino-2-benzothiazolecarbonitrile is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals for its ability to contribute to the development of new drugs and pesticides.
Used in Dye and Pigment Production:
6-Amino-2-benzothiazolecarbonitrile is used as a key intermediate in the production of dyes and pigments, due to its chemical properties that facilitate color creation and stability.
Used in Rubber Chemical Manufacturing:
In the rubber industry, 6-Amino-2-benzothiazolecarbonitrile is used as a component in the manufacturing of rubber chemicals, enhancing the performance and durability of rubber products.
Used as Antioxidants:
6-Amino-2-benzothiazolecarbonitrile is utilized in the creation of antioxidants, which are essential in preventing the degradation of materials and extending their lifespan.
Used in Biologically Active Compounds Synthesis:
6-Amino-2-benzothiazolecarbonitrile is used as a building block in the synthesis of biologically active compounds, playing a crucial role in pharmaceutical research and development for potential therapeutic applications.
Used in Material Science and Organic Synthesis:
6-Amino-2-benzothiazolecarbonitrile may have potential uses in material science and organic synthesis, indicating its broad applicability in creating new materials and advancing chemical reactions.

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

Downstream Products

• 118969-27-0 2-(6-aminobenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 934270-96-9 6-((4-benzyloxycarbonylaminophenyl)ethylamino)-2-cyanobenzothiazole 
• 912641-81-7 tert-butyl 2-(2-cyanobenzo[d]thiazol-6-ylamino)-2-oxoethylcarbamate 
• 1289513-02-5 tert-butyl 1-(2-(2-cyanobenzo[d]thiazol-6-ylamino)-2-oxoethylamino)-1-oxo-3-(tritylthio)propan-2-ylcarbamate 
• 1207738-16-6 tert-butyl 1-(2-cyanobenzo[d]thiazol-6-ylamino)-1-oxo-3-(tritylthio)propan-2-ylcarbamate 
• 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 

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.

A sequentially activated bioluminescent probe for observation of cellular H2O2production induced by cysteine

We report herein a caged luciferin probeCy-Hyas a sequentially activated probe to selectively and sensitively sensel-Cys and H2O2. The probe displayed fluorescence and bioluminescence responses toward the two analytes. Utilizing the present probe, cellular excessl-Cys-induced H2O2up-regulation was observed for the first time in living MDA-MB-231 cells.

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.

Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy

Abstract: The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method. Graphical Abstract: [Figure not available: see fulltext.].

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.

Rapid and scalable assembly of firefly luciferase substrates

Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is

A "caged" Luciferin for Imaging Cell-Cell Contacts

Cell-cell interactions underlie fundamental biological processes but remain difficult to visualize over long times and large distances in tissues and live organisms. Bioluminescence imaging with luciferase-luciferin pairs is sufficiently sensitive to imag

Site-specific immobilization of biomolecules by a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole

We report herein a new site-specific microarray immobilization method based on a biocompatible reaction between terminal cysteine and 2-cyanobenzothiazole (CBT). This immobilization strategy has been successfully applied to anchor small molecules, peptides and proteins onto microarrays.

METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS

Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives

METHODS AND SYSTEMS FOR SYNTHESIS OF A D-AMINOLUCIFERIN PRECURSOR AND RELATED COMPOUNDS

Methods and systems to generate 6-amino-6-deoxy-D-luciferin precursor, 2-cyano-6-aminobenzothiazole and related compounds and derivatives