135595-17-4

Basic information

• Product Name: 4-(2-CHLOROPHENYL)-4-OXOBUTYRONITRILE
• Synonyms: 4-(2-CHLOROPHENYL)-4-OXOBUTYRONITRILE
• CAS NO: 135595-17-4
• Molecular Formula: C10H8ClNO
• Molecular Weight: 193.63
• Mol File: 135595-17-4.mol

Chemical Properties

• Boiling Point: 331.3°C at 760 mmHg
• Flash Point: 154.2°C
• Appearance: /
• Density: 1.215g/cm³
• Vapor Pressure: 0.000157mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: 4-(2-CHLOROPHENYL)-4-OXOBUTYRONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-CHLOROPHENYL)-4-OXOBUTYRONITRILE(135595-17-4)
• EPA Substance Registry System: 4-(2-CHLOROPHENYL)-4-OXOBUTYRONITRILE(135595-17-4)

Safety Data

• Hazardous Substances Data: 135595-17-4(Hazardous Substances Data)

Usage

Physical Appearance

Yellow to brown crystalline solid

Common Uses

Intermediate in pharmaceutical and agrochemical synthesis, building block in heterocyclic compound production and organic materials

Hazards

Irritant to eyes, skin, and respiratory system

Safety Precautions

Handle with proper safety precautions, store in a well-ventilated area, and tightly sealed container.

InChI:InChI=1/C10H8ClNO/c11-9-5-2-1-4-8(9)10(13)6-3-7-12/h1-2,4-5H,3,6H2

Upstream product

• 2039-87-4 2-chlorostyrene 
• 75-05-8 acetonitrile 
• 89-98-5 2-chloro-benzaldehyde 
• 107-13-1 acrylonitrile 
• 24654-08-8 3-(2-chlorophenyl)prop-2-ynoic acid 
• 609-65-4 o-chlorobenzoyl chloride 

Relevant articles and documents

Unactivated C(sp3)-H Bond Functionalization of Alkyl Nitriles with Vinylarenes and Mechanistic Studies

The first example of a metal-free unactivated C(sp3)-H bond functionalization of alkyl nitriles with terminal vinylarenes to provide γ-ketonitrile derivatives is described. This protocol features simple operations, a broad substrate scope, and atom and step economy. In addition, Cu-catalyzed C(sp3)-H bond functionalization of azodiisobutyronitrile (AIBN) and analogues with terminal vinylarenes to generate γ-ketonitriles was also studied. A preliminary free-radical pathway was confirmed by capturing an alkyl radical, and a conjugate system was found that can stabilize radical intermediates and be in favor of this transformation. Density functional theory (DFT) calculations also provide important evidence of the free-radical pathway.

Facile Synthesis of γ-Ketonitriles in Water via C(sp2)–H Activation of Aromatic Aldehydes over Cu?g-C3N4 under Visible-Light

A facile C(sp2)–H activation of aldehyde under visible-light conditions using Cu?g-C3N4 as photocatalyst and water as solvent is reported. The envisaged method involves photocatalytic intermolecular Stetter reaction using

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of ?-Diketones and ?-Ketonitriles

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to ?-diketones and ?-ketonitriles. A possible mechanism is proposed.

A new method for the synthesis of γ-oxobutyronitriles via addition of aroyl chlorides to acrylonitrile promoted by samarium metal in DMF

Without any pretreatment or activator, metallic samarium in DMF promotes the addition of aroyl chlorides to acrylonitrile to form γ -oxobutyronitriles.