40805-50-3

Basic information

• Product Name: Benzonitrile, 4-(chloroacetyl)- (9CI)
• Synonyms: Benzonitrile, 4-(chloroacetyl)- (9CI);4-(2-chloroacetyl)benzonitrile;4-Cyanophenacyl chloride;alpha-Chloro-4'-cyanoacetophenone;4-(Chloroacetyl)benzonitrile
• CAS NO: 40805-50-3
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.60304
• Product Categories: ACETYLHALIDE
• Mol File: 40805-50-3.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 340.1°C at 760 mmHg
• Flash Point: 159.5°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 8.77E-05mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: Benzonitrile, 4-(chloroacetyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(chloroacetyl)- (9CI)(40805-50-3)
• EPA Substance Registry System: Benzonitrile, 4-(chloroacetyl)- (9CI)(40805-50-3)

Safety Data

• Hazardous Substances Data: 40805-50-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzonitrile, 4-(chloroacetyl)(9CI) is used as a synthetic intermediate for the development of pharmaceuticals. Its unique reactivity allows for the creation of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, Benzonitrile, 4-(chloroacetyl)(9CI) serves as a key intermediate in the synthesis of various agrochemicals. Its ability to react with multiple functional groups contributes to the development of effective compounds for agricultural use.
Used in Organic Compounds Synthesis:
Benzonitrile, 4-(chloroacetyl)(9CI) is utilized as an intermediate in the synthesis of other organic compounds, broadening its applications beyond the pharmaceutical and agrochemical industries. Its versatility in organic chemistry makes it a valuable component in the creation of diverse chemical entities.
It is crucial to handle Benzonitrile, 4-(chloroacetyl)(9CI) with care due to its potential toxicity and flammability, ensuring safety in its use across different industries.

InChI:InChI=1/C9H6ClNO/c10-5-9(12)8-3-1-7(6-11)2-4-8/h1-4H,5H2

Upstream product

• 2631-71-2 4-aminophenacyl chloride 
• 3490-50-4 2-diazo-1-(4-cyanophenyl)ethanone 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 623-00-7 4-bromobenzenecarbonitrile 
• 79-04-9 chloroacetyl chloride 
• 619-65-8 4-cyanobenzoic Acid 
• 6068-72-0 4-cyanobenzoyl chlorIde 
• 3435-51-6 4-ethenylbenzonitrile 

Downstream Products

• 1443-80-7 4-cyanophenyl methyl ketone 
• 1001615-58-2 1-(p-Cyanophenyl)-4-pentene-1-one 
• 1198464-13-9 4-(2-phenyl-1H-indole-3-carbonyl)benzonitrile 
• 622787-69-3 2-azido-1-(4'-cyanophenyl)ethanone 
• 179694-33-8 (S)-(+)-2-(4-cyanophenyl)oxirane 
• 1035374-47-0 4-((2S)-morpholin-2-yl)benzonitrile hydrochloride 
• 1444827-60-4 5-(4-cyanobenzoyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 241479-67-4 Isavuconazole 

Relevant articles and documents

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions

A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

The Mn-catalyzed paired electrochemical facile oxychlorination of styrenes: Via the oxygen reduction reaction

Reported herein is the electrochemical engendering of chlorine radicals by a manganese catalyst with a controllable pattern, and inexpensive MgCl2 as the chlorine source. In combination with the oxygen reduction reaction, chloroacetophenones were synthesized with abundant styrene as the feedstock in good to excellent yields.

CV-driven Optimization: Cobalt-Catalyzed Electrochemical Expedient Oxychlorination of Alkenes via ORR

Instead of screening reaction conditions by yield-based chemical trial-and-error, potential-based cyclic voltammetry was alternatively employed for optimization of electrochemical oxychlorination of alkenes. With this unconventional screening method, the catalyst system including catalysts, molar ratio of chloride sources and solvents were identified in a rational, time- and energy-efficient manner. The optimal catalytic system in combination with oxygen reduction reaction enabled broad substrate scopes for the desired transformation by taking advantages of persistent radical effect. UV-vis and CV titration experiments confirmed the in-situ formed catalytic species [CoCl5]. Moreover, cyclic voltammetry was applied to obtain mechanistic insights in our reaction system. (Figure presented.).

Systematic Synthesis of Diphenyl-Substituted Carotenoids as Molecular Wires

A general method for the construction of diphenyl-substituted carotenoids has been developed through the stereoselective synthesis of dienyl sulfones with a phenyl substituent. Systematic synthetic pathways to the dienyl sulfones were delineated starting from readily available acetophenones with para-substituent X of various electronic natures, which provided the carotenoids with diverse physicochemical characteristics. The sulfone olefination method together with the Ramberg–B?cklund reaction produced a 9,9′-cis-10,10′-diphenylcarotene and all-trans-9,9′-diphenylcarotenes. Conductance measurements of the all-trans carotenoids by the scanning tunnelling microscopy break-junction method revealed a positional effect of the phenyl groups as well as a polar effect of the phenyl substituent X according to the electronic nature.

NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

The invention relates to novel arylalkenylpropargylamine derivatives of general formula (I) or enantiomers or diastereomers thereof or salts, optionally pharmaceutically acceptable salts, or solvates of any of these. The compounds can be used in treating or preventing a disease or condition in a mammal related to monoamine oxidase dysfunction, especially in neurodegenerative diseases, e.g. Parkinson's disease, Alzheimer's disease or Huntington's disease.

Pd-catalyzed domino carbonylative-decarboxylative allylation: An easy and selective monoallylation of ketones

In the presence of an allyl alcohol, α-chloroacetophenones undergo an allyloxycarbonylation reaction followed by in situ decarboxylative allylation to selectively afford the corresponding monoallylated ketones via a Pd-catalyzed domino sequence. The scope of the reaction was extended to substituted α-chloroacetophenones as well as various allyl alcohols.

Combining designer cells and click chemistry for a one-pot four-step preparation of enantiopure β-hydroxytriazoles

The multistep catalytic process using designer cells, either added as freshly prepared suspensions or as stable lyophilized powder, and click reaction can be performed in one pot. The sequence of four reactions allows the production of both enantiomers of β-hydroxytriazoles with high enantiomeric excess.

Preparation of functionalized α-chloromethyl ketones using Rieke zinc

The cross-coupling reaction of highly functionalized organozinc reagents with chloroacetyl chloride mediated by copper allows for the easy preparation of functionalized α-chloromethyl ketones in excellent yields.

Carbon-13 NMR Spectra of Some 4-Substituted Phenacyl Chlorides and Iodides

The 13C NMR signals for some 4-substituted phenacyl chlorides and iodides were assigned.The carbonyl carbons exhibit upfield shifts compared with those of the corresponding 4-substituted acethophenones; in the chlorinated derivatives a downfield shift is observed for the α-methylene carbons, while a reverse effect occurs in the iodinated compounds.The chemical shifts of the aromatic ring carbons are in close agreement with those calculated using substituent chemical shifts.KEY WORDS 13C NMR 4-substituted pheacyl chlorides and iodides