78583-84-3

Basic information

• Product Name: 3-CHLORO-3-PHENYL-ACRYLONITRILE
• Synonyms: 3-chloro-3-phenyl-2-Propenenitrile
• CAS NO: 78583-84-3
• Molecular Formula: C₉H₆ClN
• Molecular Weight: 163.6
• Mol File: 78583-84-3.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 276.4°C at 760 mmHg
• Flash Point: 118.2°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 0.00482mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: 3-CHLORO-3-PHENYL-ACRYLONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-3-PHENYL-ACRYLONITRILE(78583-84-3)
• EPA Substance Registry System: 3-CHLORO-3-PHENYL-ACRYLONITRILE(78583-84-3)

Safety Data

• Hazardous Substances Data: 78583-84-3(Hazardous Substances Data)

Usage

Description

3-Chloro-3-phenyl-acrylonitrile, also known as 3-(3-chlorophenyl)acrylonitrile, is a chemical compound with the molecular formula C9H6ClN. It is a colorless to light yellow liquid with a strong and distinct odor. 3-CHLORO-3-PHENYL-ACRYLONITRILE is known for its versatile applications in various industries, primarily as a precursor in the synthesis of pharmaceuticals, agrochemicals, and dyes. It also serves as an intermediate in organic synthesis for producing a range of other chemical compounds. Furthermore, 3-chloro-3-phenyl-acrylonitrile is utilized in the development of new materials and as a building block in the synthesis of specialty polymers. However, due to its potential health hazards and reactivity, it is crucial to handle this chemical with care.

Uses

Used in Pharmaceutical Industry:
3-Chloro-3-phenyl-acrylonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-chloro-3-phenyl-acrylonitrile is employed as a precursor for the production of agrochemicals, such as pesticides and herbicides. Its reactivity and chemical properties make it suitable for the creation of effective and targeted agrochemicals.
Used in Dye Industry:
3-Chloro-3-phenyl-acrylonitrile is used as a building block in the synthesis of various dyes. Its chemical structure contributes to the development of dyes with specific color properties and stability.
Used in Organic Synthesis:
3-Chloro-3-phenyl-acrylonitrile is utilized as an intermediate in organic synthesis to produce a variety of other chemical compounds. Its versatility allows for the creation of different chemical entities with diverse applications.
Used in Material Science:
In the field of material science, 3-chloro-3-phenyl-acrylonitrile is employed in the development of new materials. Its unique properties contribute to the creation of materials with specific characteristics, such as improved strength, durability, or chemical resistance.
Used in Specialty Polymers Synthesis:
3-Chloro-3-phenyl-acrylonitrile is used as a building block in the synthesis of specialty polymers. Its incorporation into polymer structures allows for the development of polymers with tailored properties, such as enhanced thermal stability, mechanical strength, or chemical resistance.

InChI:InChI=1/C9H6ClN/c10-9(6-7-11)8-4-2-1-3-5-8/h1-6H/b9-6-

Upstream product

• 33603-87-1 β-chlorocinnamaldehyde 
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• 39812-71-0 3-chloro-3-phenyl-1-prop-2-en-1-yliden-dimethyliminium perchlorate 
• 60-29-7 diethyl ether 
• 10026-13-8 phosphorus pentachloride 
• 72806-43-0 β-chloro-cis-cinnamaldehyde seqcis-oxime 
• 108-24-7 acetic anhydride 

Downstream Products

• 92133-84-1 4-Methyl-N-(1-methyl-5-phenyl-1H-pyrazol-3-yl)-benzenesulfonamide 
• 92133-90-9 4-Methyl-N-(2-methyl-5-phenyl-2H-pyrazol-3-yl)-benzenesulfonamide 
• 1045703-73-8 3-amino-5-phenyl-2-selenophenecarbonitrile 
• 83060-72-4 3-amino-5-phenylthiophene-2-carbonitrile 
• 100063-22-7 methyl 3-amino-5-phenylthiophene-2-carboxylate 
• 614-16-4 Benzoylacetonitrile 

Relevant articles and documents

Regio- and Stereoselective Chlorocyanation of Alkynes

A variety of terminal and internal alkynes were converted regio- and stereoselectively into (Z)-3-chloroacrylonitriles by treatment with BCl3 in the presence of stoichiometric amounts of imidazolium thiocyanates. These products could be readily functionalized to provide useful building blocks, thus demonstrating the synthetic value of the method. Preliminary mechanistic studies suggest initial activation of the cationic thiocyanate by the Lewis acid, followed by electrophilic attack of the alkyne. The syn addition of a chloride to the vinyl cation intermediate and final elimination of the thiourea unit afford the desired chloroacrylonitriles.

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Design, Synthesis, and Biological Evaluation of 6-Substituted Thieno[3,2- d]pyrimidine Analogues as Dual Epidermal Growth Factor Receptor Kinase and Microtubule Inhibitors

The clinical evidence for the success of tyrosine kinase inhibitors in combination with microtubule-targeting agents prompted us to design and develop single agents that possess both epidermal growth factor receptor (EGFR) kinase and tubulin polymerization inhibitory properties. A series of 6-aryl/heteroaryl-4-(3′,4′,5′-trimethoxyanilino)thieno[3,2-d]pyrimidine derivatives were discovered as novel dual tubulin polymerization and EGFR kinase inhibitors. The 4-(3′,4′,5′-trimethoxyanilino)-6-(p-tolyl)thieno[3,2-d]pyrimidine derivative 6g was the most potent compound of the series as an antiproliferative agent, with half-maximal inhibitory concentration (IC50) values in the single- or double-digit nanomolar range. Compound 6g bound to tubulin in the colchicine site and inhibited tubulin assembly with an IC50 value of 0.71 μM, and 6g inhibited EGFR activity with an IC50 value of 30 nM. Our data suggested that the excellent in vitro and in vivo profile of 6g may be derived from its dual inhibition of tubulin polymerization and EGFR kinase.