2-Chloroacrylonitrile

Base Information

• Chemical Name: 2-Chloroacrylonitrile
• CAS No.: 920-37-6
• Molecular Formula: C3H2ClN
• Molecular Weight: 87.5086
• Hs Code.: 29269095
• European Community (EC) Number: 213-055-2
• NSC Number: 511714
• UN Number: 1993
• UNII: FFJ1QHD154
• DSSTox Substance ID: DTXSID6052613
• Nikkaji Number: J55.139B
• Wikidata: Q27277955
• Mol file: 920-37-6.mol

Synonyms:2-chloroacrylonitrile;alpha-chloroacrylonitrile

Chemical Property of 2-Chloroacrylonitrile

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 58.4mmHg at 25°C
• Melting Point: -65 °C(lit.)
• Refractive Index: n20/D 1.429(lit.)
• Boiling Point: 89.5 °C at 760 mmHg
• Flash Point: 6.7 °C
• PSA: 23.79000
• Density: 1.125 g/cm³
• LogP: 1.26248
• Storage Temp.: Flammables area
• Solubility.: Chloroform, Ethyl Acetate, Methanol (Very Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 86.9875768
• Heavy Atom Count: 5
• Complexity: 86.3
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

2-Chloroacrylonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, T+, T, N
• Hazard Codes: F,T+,T,N
• Statements: 45-24-26/28-34-43-50-40-36/37/38-28-23/24-11
• Safety Statements: 53-26-36/37/39-45-61-28A-16-1-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C=C(C#N)Cl
• Uses: Common reagent in cycloaddition reactions.1,2 2-Chloroacrylonitrile (cas# 920-37-6) is a compound useful in organic synthesis.

Technology Process of 2-Chloroacrylonitrile

There total 14 articles about 2-Chloroacrylonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

2,3-dichloropropionitrile (2601-89-0) → 2-Chloroacrylonitrile (920-37-6)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1021/ol7021142

Reference yield: 77.0%

1-methoxy-3,4,5-trimethyl-1,4-cyclohexadiene (40672-22-8) → 2-Chloroacrylonitrile (920-37-6)

Guidance literature:

With hydroquinone; 2-Chloroacrylonitrile; In toluene; at 0 ℃; Heating;

DOI:10.1246/bcsj.59.2521

Reference yield: 39.0%

→ 2-Chloroacrylonitrile (920-37-6)

Guidance literature:

upstream raw materials:

2,2,3-trichloropropionitrile

acrylonitrile

potassium cyanide

2,3-dichloropropionitrile

Downstream raw materials:

N-(2-chloro-2-cyano-ethyl)-phthalamic acid methyl ester

butenedinitrile

3ξ-benzylsulfanyl-acrylonitrile

chloro-2 thiobenzyl-3 propionitrile

Refernces

Asymmetric conjugate addition of oxindoles to 2-chloroacrylonitrile: A highly effective organocatalytic strategy for simultaneous construction of 1,3-nonadjacent stereocenters leading to chiral pyrroloindolines

10.1002/chem.201002563

The research primarily focuses on the development of an asymmetric conjugate addition reaction of 3-substituted oxindoles to 2-chloroacrylonitrile, utilizing a chiral alkyl thiourea as a catalyst. This reaction is significant for the construction of chiral pyrroloindoline structures, which are key components in many biologically active indole alkaloids. The experiments involved screening various bifunctional tertiary amine thioureas or urea catalysts to optimize the reaction conditions, ultimately achieving high yields and excellent stereoselectivity. Reactants included 3-substituted oxindoles and 2-chloroacrylonitrile, with the catalysts being screened at low temperatures. Analyses used to determine the success of the reactions included 1H NMR spectroscopy for diastereomeric ratios and chiral HPLC analysis for enantiomeric excess. The optimized conditions were identified as using 4a catalyst in 1,2-dichloroethane at -20°C with 4 ? molecular sieves, yielding products with up to >30:1 dr and up to 99% ee.