26152-02-3

Basic information

• Product Name: (3-CHLORO-PHENYL)-OXO-ACETONITRILE
• Synonyms: 3-CHLOROBENZOYL CYANIDE;(3-CHLORO-PHENYL)-OXO-ACETONITRILE;Benzeneacetonitrile, 3-chloro-a-oxo-
• CAS NO: 26152-02-3
• Molecular Formula: C₈H₄ClNO
• Molecular Weight: 165.58
• Mol File: 26152-02-3.mol

Chemical Properties

• Boiling Point: 259.774ºC at 760 mmHg
• Flash Point: 110.908 ºC
• Appearance: /
• Density: 1.311 g/cm³
• CAS DataBase Reference: (3-CHLORO-PHENYL)-OXO-ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (3-CHLORO-PHENYL)-OXO-ACETONITRILE(26152-02-3)
• EPA Substance Registry System: (3-CHLORO-PHENYL)-OXO-ACETONITRILE(26152-02-3)

Safety Data

• Hazardous Substances Data: 26152-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3-Chloro-phenyl)-oxo-acetonitrile is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its chemical structure allows for the development of new drugs and the modification of existing ones, contributing to advancements in medicinal chemistry.
Used in Agrochemical Production:
In the agrochemical sector, (3-Chloro-phenyl)-oxo-acetonitrile serves as a building block for the creation of pesticides and other crop protection agents. Its role in this industry is crucial for enhancing agricultural productivity and ensuring food security.
Used in Fine Chemicals Manufacturing:
(3-Chloro-phenyl)-oxo-acetonitrile is employed in the production of fine chemicals, which are high-purity, specialty chemicals used in various applications, including research, diagnostics, and high-value industrial processes.
Used in Dye and Pigment Industries:
(3-Chloro-phenyl)-oxo-acetonitrile is also used in the manufacturing of dyes and pigments, where its unique properties contribute to the development of new colorants and the improvement of existing ones, catering to the demands of various industries such as textiles, plastics, and printing.
Overall, (3-Chloro-phenyl)-oxo-acetonitrile is a multifaceted chemical with significant applications in the pharmaceutical, agrochemical, fine chemicals, and dye/pigment industries, showcasing its importance in the realm of chemical synthesis and material development.

Upstream product

• 57-12-5 cyanide^(1-) 
• 37156-42-6 4-nitrophenyl 3-chlorobenzoate 
• 618-46-2 m-Chlorobenzoyl chloride 
• 544-92-3 copper(I) cyanide 
• 7677-24-9 trimethylsilyl cyanide 
• 1529-41-5 3-chloro-benzeneacetonitrile 
• 30070-63-4 meta-chlorobenzoic anhydride 
• 37156-55-1 2,4-dinitrophenyl 3-chlorobenzoate 

Downstream Products

• 26767-07-7 2-(3-chlorophenyl)-2-oxoacetic acid 
• 535-80-8 3-chlorobenzoate 

Relevant articles and documents

Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst

We developed a synthetic method toward benzoyl cyanide through aerobic photooxidation of benzyl cyanide in the presence of carbon tetrabromide under visible light irradiation with fluorescent lamps.

ZnI2-catalyzed cyanation of acyl chlorides with TMS-CN: An interesting role of iodine

Both aliphatic and aromatic acyl cyanides have been synthesized with TMSCN and acyl chloride with ZnI2 (0.5 mol%). However the in situ generated I2 is proposed accounting for the formation of by-product O-TMS enolate at high catalyst loading rather than 0.5 mol%. Asymmetric reduction of benzoyl cyanide with borane has been explored in 82% yield and 24% ee.

AgI-PEG400-KI catalyzed environmentally benign synthesis of aroyl cyanides using potassium hexacyanoferrate(II) as the cyanating agent

A practical cyanation of aroyl chlorides with 0.2 equivalent of non-toxic cyanide source, K4[Fe(CN)6], 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system is described. The reactions were performed in DMF at room temperature and provided the corresponding aroyl cyanides in 64-89% yield, typically in less than ten hours. Georg Thieme Verlag Stuttgart.

Structure-reactivity correlations in nucleophilic substitution reactions of Y-substituted phenyl X-substituted benzoates with anionic and neutral nucleophiles

A kinetic study is reported for the reactions of 4-nitrophenyl X-substituted benzoates (1a-l) and Y-substituted phenyl benzoates (2a-l) with two anionic nucleophiles (OH- and CN-) and three amines (piperidine, hydrazine, and glycylglycine) in 80 mol% H2O-20 mol% dimethyl sulfoxide (DMSO) at 25.0 ± 0.1 °C. Each Hammett plot exhibits two intersecting straight lines for the reactions of 1a-l with the anionic nucleophiles and piperidine, while the Yukawa-Tsuno plots for the same reactions are linear. The Hammett plots for the reactions of 2a-l with hydrazine and glycylglycine demonstrate much better linear correlations with σ- constants than with σ° or σ constants, indicating that the leaving group departure occurs at the rate determining step (RDS). On the contrary, σ- constants result in poorer Hammett correlation than σ° constants for the corresponding reactions with OH- and CN-, indicating that the leaving group departure occurs after the RDS for the reactions with the anionic nucleophiles. The large ρX value (1.7 ± 0.1) obtained for the reactions of 1a-l with the anionic nucleophiles supports the proposal that the reactions proceed through an addition intermediate with its formation being the RDS. The Royal Society of Chemistry 2006.

Method for producing optically active mandelic acid derivatives

The present invention provides a method for enzymatically producing optically active mandelic acid derivatives. An optically active mandelic acid derivative (shown as Formula II) is produced by reacting a culture or cell body of a microorganism, or processed products thereof, with a phenylglyoxylic acid derivative, and then recovering the obtained optically active mandelic acid derivative, wherein the microorganism has the ability to stereo-selectively reduce the phenylglyoxylic acid derivative. An optically active mandelic acid obtained according to the present invention is useful as an intermediate for the synthesis of pharmaceuticals and agricultural chemicals.

Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization

A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.

Preparation of acyl cyanides

Acyl cyanides of the formula STR1 in which R represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms or an optionally substituted aryl group, or an optionally substituted 5-membered or 6-membered heterocyclic radical which additionally can be fused to a benzene ring, are obtained in high yields by reacting carboxylic acid anhydrides of the formula R--CO--O--CO--R (II) with trimethylsilyl cyanide, (CH3)3 Si--CN (III), if appropriate in the presence of a catalyst and, if appropriate, in the presence of a diluent, at a temperature between 50° and 250° C. The acyl cyanides can be used as intermediate products, for example, for the preparation of certain herbicidally active compounds of the triazinone series.

Process for the preparation of acyl cyanides

Acyl cyanides of the general formula STR1 in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, are prepared by reacting the corresponding carboxylic acid anhydride with an alkali metal cyanide or anhydrous hydrocyanic acid, at a temperature of between 50° and 250° C. and the resulting acyl cyanide is removed from the reaction medium by distillation, immediately after it has been formed.