6136-62-5

Basic information

• Product Name: 3-benzoylbenzonitrile
• Synonyms: 3-benzoylbenzonitrile;Einecs 228-109-0
• CAS NO: 6136-62-5
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 207.22736
• EINECS: 228-109-0
• Mol File: 6136-62-5.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 365.8°C at 760 mmHg
• Flash Point: 175°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.53E-05mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: 3-benzoylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-benzoylbenzonitrile(6136-62-5)
• EPA Substance Registry System: 3-benzoylbenzonitrile(6136-62-5)

Safety Data

• Hazardous Substances Data: 6136-62-5(Hazardous Substances Data)

Usage

General Description

3-Benzoylbenzonitrile, also known as 2-Benzoylbenzonitrile, is an organic compound with the chemical formula C14H9NO. It is a white to off-white solid that is sparingly soluble in water but soluble in organic solvents. 3-Benzoylbenzonitrile is widely used in the synthesis of pharmaceuticals, dyes, and other organic compounds due to its versatile reactivity and ability to serve as a building block in various chemical reactions. It is also utilized as an intermediate in the production of other aromatic compounds and as a reagent in organic synthesis. Additionally, 3-Benzoylbenzonitrile exhibits some biological activities and has been studied for its potential use in drug development and medicinal chemistry.

InChI:InChI=1/C14H9NO/c15-10-11-5-4-8-13(9-11)14(16)12-6-2-1-3-7-12/h1-9H

Upstream product

• 13428-06-3 3-(hydroxy(phenyl)methyl)benzonitrile 
• 6952-59-6 3-cyanobromobenzene 
• 98-88-4 benzoyl chloride 
• 611-73-4 Benzoylformic acid 
• 59089-08-6 trans-3-cyano stilbene 
• 69113-59-3 3-iodobenzonitrile 
• 135364-97-5 tert-butyl benzoyl(tert-butoxycarbonyl)carbamate 
• 591-50-4 iodobenzene 
• 67-66-3 chloroform 
• 150255-96-2 (3‐cyanophenyl)boronic acid 
• 98-80-6 phenylboronic acid 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 201230-82-2 carbon monoxide 
• 93-98-1 N-phenyl benzoyl amide 

Downstream Products

• 101168-85-8 1-[3-(1-hydroxy-1-phenyl-ethyl)-phenyl]-ethanone 
• 6136-68-1 3-acethylbenzonitrile 
• 197792-35-1 C₁₈H₁₅NO₂ 
• 74672-16-5 [3-((phenylmethyl)phenyl)methyl]amine 
• 13391-41-8 3-(alpha-chlorobenzyl)benzonitrile 
• 21204-86-4 m-benzoylbenzoic acid methyl ester 
• 73831-68-2 4-tert-butyl-3-cyano-benzophenone 
• 73831-67-1 3-(1-Hydroxy-2,2-dimethyl-1-phenyl-propyl)-benzonitrile 
• 13428-06-3 3-(hydroxy(phenyl)methyl)benzonitrile 
• 579-18-0 3-benzoylbenzoic acid 

Relevant articles and documents

Novelmeta-benzothiazole and benzimidazole functionalised POCOP-Ni(ii) pincer complexes as efficient catalysts in the production of diarylketones

The synthesis of four novel non-symmetric Ni(ii)-POCOP pincer complexesmeta-functionalized with either benzothiazole or benzimidazole at the central aryl ring is described. All complexes were fully characterised in solution by various analytical techniques and the molecular structures in the solid state of complexes1b,2aand2bwere unequivocally determined by single crystal X-ray diffraction analysis. In addition, the Ni(ii)-POCOP pincer complexes were efficiently used as catalysts in the synthesis of diarylketones by cross-coupling reactions of functionalized benzaldehydes and boronic acid derivatives under relatively mild conditions. An important aspect of this transformation is the dependence on the steric properties of the donor groups (OPR2) of the pincer ligands, the more active compounds having the phosphinitos bearing isopropyl groups (1aand2a) than those containingtert-butyl substituents (1band2b).

Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic controlvs.kinetic control ofN,N-Boc2-amides

A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides (N-methoxy-N-methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N-C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest.

Kinetically Controlled, Highly Chemoselective Acylation of Functionalized Grignard Reagents with Amides by N?C Cleavage

The direct transition-metal-free acylation of amides with functionalized Grignard reagents by highly chemoselective N?C cleavage under kinetic control has been accomplished. The method offers rapid and convergent access to functionalized biaryl ketones through transient tetrahedral intermediates. The direct access to functionalized Grignard reagents by in situ halogen–magnesium exchange promoted by the versatile turbo-Grignard reagent (iPrMgCl?LiCl) permits excellent substrate scope with respect to both the amide and Grignard coupling partners. These reactions enable facile, operationally simple and chemoselective access to tetrahedral intermediates from amides under significantly milder conditions than chelation-controlled intermediates. This novel direct two-component coupling sets the stage for using amides as acylating reagents in an alternative paradigm to the metal-chelated approach, acyl metals and Weinreb amides.