42787-75-7

Basic information

• Product Name: 5-Cyano-5H-dibenz[b,f]azepine
• Synonyms: 5H-DIBENZO[B,F]AZEPINE 5-CARBONITRILE;5-CYANO-5H-DIBENZO(B,F)AZEPINE;DIBENZ[B,F]AZEPINE-5-CARBONITRILE;5H-dibenz[b,f]azepine-5-carbonitrile;10,11-dihdyro-10,11-epoxy-5H-dibenz(b.f)azepine-5-carboxamide;5-cyano dibenz(b.f)azepine;DIBENZO(B,F)AZEPINE-5-CARBONITRILE;5H-Dibenz(b,f)azepin-5-carbonitril
• CAS NO: 42787-75-7
• Molecular Formula: C₁₅H₁₀N₂
• Molecular Weight: 218.25
• EINECS: 255-944-8
• Mol File: 42787-75-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 106-110 °C(lit.)
• Boiling Point: 410.4 °C at 760 mmHg
• Flash Point: 183.3 °C
• Appearance: /
• Density: 1.25 g/cm³
• CAS DataBase Reference: 5-Cyano-5H-dibenz[b,f]azepine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyano-5H-dibenz[b,f]azepine(42787-75-7)
• EPA Substance Registry System: 5-Cyano-5H-dibenz[b,f]azepine(42787-75-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 42787-75-7(Hazardous Substances Data)

Usage

General Description

5-Cyano-5H-dibenz[b,f]azepine is a chemical compound that belongs to the dibenzazepine class of organic compounds. It is a tricyclic compound containing a dibenzazepine skeleton with a cyanide group attached at the 5th position. 5-Cyano-5H-dibenz[b,f]azepine has potential applications in the field of pharmaceuticals as it shows promising antidepressant and anticonvulsant properties. It is also used as a building block in the synthesis of various other chemicals and pharmaceuticals. Additionally, 5-Cyano-5H-dibenz[b,f]azepine has been studied for its potential use as a fluorescent probe for the detection of various analytes in biological and environmental samples.

InChI:InChI=1/C15H10N2/c16-11-17-14-7-3-1-5-12(14)9-10-13-6-2-4-8-15(13)17/h1-10H

Upstream product

• 256-96-2 dibenzoazepine 
• 506-77-4 cyanogen chloride 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 506-68-3 bromocyane 
• 298-46-4 carbamazepin 

Downstream Products

• 298-46-4 carbamazepin 
• 78880-65-6 5-cyano-10-oxo-10,11-dihydro-5H-dibenz[b,f]-azepine 
• 78880-63-4 5-cyano-10-nitro-5H-dibenz[b,f]azepine 

Relevant articles and documents

Substituent-Dependent Reactivity in the Photodimerization of N-Substituted Dibenz[b,f]azepines

The photoprocesses of a series of N-substituted dibenz[b,f]azepines (iminostilbenes) were studied by absorption and emission spectroscopy, by laser flash photolysis, and by preparative irradiation with NMR analysis. In solutions, 2π+2π photodimers of N-cyano and N-acyl dibenzazepines are formed via the triplet state upon acetone- or benzophenone-sensitized energy transfer. T-T absorption spectra were measured and absorption coefficients were determined. The triplet energy transfer is equally efficient for N-alkyl dibenzazepines, which do not dimerize. Excited states of nπ* character in the latter cases are discussed to rationalize the different reactivities. In spite of negligible intersystem crossing of 21 dibenzazepine derivatives, photodimers of N-acyl and N-cyano dibenzazepines are formed upon direct excitation in concentrated solutions (0.01-0.1 moldm-3) as well as in the solid state. A selective anti-configuration of the photodimers was found throughout.

A METHOD FOR PREPARING 5H-CYANO-IMIDO STILBENE

A method for preparing 5-cyano-5H-dibenz[b,f]azepine, comprises: reacting carbamazepine of formula (II) used as dehydrating agent with bis(trichloromethyl)carbonate of formula (III) in organic solvent for 1-30 hours at 20-150°C, and obtaining 5-cyano-5H-dibenz[b,f]azepine (I) after the post-treatment of the reaction solution. The scheme is shown as below.

Activated dimethyl sulfoxide dehydration of amide and its application to one-pot preparation of benzyl-type perfluoroimidates

Various types of primary amides were treated under an activated dimethyl sulfoxide (DMSO) species, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain nitriles in excellent yield. This dehydration system was extended to a one-pot preparation of perfluoroimidates via volatile perfluoronitriles from perfluoroamides. Fifteen benzyl-type perfluoroimidates can be prepared in 70-90% yield as more stable imidates than the trichloro analogue. MPM- and DMPM-perfluoroimidates can be used to protect alcohols in place of the trichloroacetimidate with excellent chemical properties and in comparable yields.