15328-32-2

Basic information

• Product Name: 1-cyanobenzotriazole
• Synonyms: 1-cyanobenzotriazole;1H-Benzotriazole-1-carbonitrile;1H-BENZO[D][1,2,3]TRIAZOLE-1-CARBONITRILE
• CAS NO: 15328-32-2
• Molecular Formula: C₇H₄N₄
• Molecular Weight: 144.13
• Mol File: 15328-32-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 73.4-74.8 °C
• Boiling Point: 300.7±25.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -1.41±0.30(Predicted)
• CAS DataBase Reference: 1-cyanobenzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cyanobenzotriazole(15328-32-2)
• EPA Substance Registry System: 1-cyanobenzotriazole(15328-32-2)

Safety Data

• Hazardous Substances Data: 15328-32-2(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic

Structure

Contains a triazole ring with a cyano group attached to the benzene ring

Common uses

a. Reagent for the modification of organic compounds and polymers
b. Versatile and efficient crosslinking agent
c. Selectively reacts with amino groups in proteins and peptides without affecting other functional groups

Applications

a. Bioconjugation chemistry
b. Synthesis of pharmaceuticals and agrochemicals

Key attributes

Reactivity and stability

Upstream product

• 95-14-7 1,2,3-Benzotriazole 
• 59016-54-5 1-cyano-4-N,N-dimethylaminopyridinium bromide 
• 506-68-3 bromocyane 
• 15217-42-2 sodium benzotriazolate 
• 143-33-9 sodium cyanide 
• 21050-95-3 N-chlorobenzotriazole 
• 43183-36-4 1-(trimethylsilyl)-1H-benzotriazole 
• 506-77-4 cyanogen chloride 

Downstream Products

• 220105-73-7 1-(toluene-4-sulfonyl)pyrrole-2-carbonitrile 
• 613-46-7 2-naphthalenecarbonitrile 
• 1210-12-4 9-cyanoanthracene 
• 935-02-4 3-Phenyl-2-propynonitrile 
• 1240350-63-3 4-[1H-1,2,3-benzotriazol-1-yl(imino)methyl]-N,N-dimethylaniline 
• 1007842-16-1 C₂₇H₄₅NO₂Si₂ 
• 59729-33-8 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile 
• 634602-53-2 methyl 4-(cyanoethynyl)benzoate 
• 151589-37-6 methyl 2-cyanoethynylbenzoate 
• 95-14-7 1,2,3-Benzotriazole 
• 496882-20-3 N,N-dibenzyl-benzotriazole-1-carboxamidine 
• 141240-68-8 1-(N¹-Phenylamidino)benzotriazole 
• 141240-69-9 1-(Benzotriazol-1-yl)-1-phenylthiomethanimine 
• 16278-99-2 2,2’-bithiophene-5-carbonitrile 

Relevant articles and documents

A Convenient New Synthesis of 1-Cyanobenzotriazole and Its Use as a C-Cyanating Reagent

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The direct electrophilic cyanation of β-keto esters and amides with cyano benziodoxole

The direct electrophilic α-cyanation of β-keto esters and amides has been developed using a hypervalent iodine benziodoxole-derived cyano reagent. The procedure is accomplished within 10 min and without the use of any catalyst in DMF, at room temperature. Thus, the highly functionalized quaternary carbon-centered nitriles were produced in high to excellent yields.

Synthesis of N-Cyanoazoles

1-Cyanoimidazole, 1-cyano-2-methylimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole were prepared by reaction of corresponding azoles with cyanogen bromide.Reactions of cyanogen bromide with sodium benzotriazolide and sodium pyridin-2-olate yield 1-cyanobenzotriazole and 2-cyanatopyridine.