3331-60-0

Basic information

• Product Name: 2-chloro-2-methylpropiononitrile
• Synonyms: 2-chloro-2-methylpropiononitrile;2-Chloro-2-methylpropanenitrile;Einecs 222-057-2
• CAS NO: 3331-60-0
• Molecular Formula: C₄H₆ClN
• Molecular Weight: 103.55014
• EINECS: 222-057-2
• Mol File: 3331-60-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 135.1°Cat760mmHg
• Flash Point: 32.1°C
• Appearance: /
• Density: 1.041g/cm³
• Vapor Pressure: 7.84mmHg at 25°C
• Refractive Index: 1.423
• CAS DataBase Reference: 2-chloro-2-methylpropiononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-2-methylpropiononitrile(3331-60-0)
• EPA Substance Registry System: 2-chloro-2-methylpropiononitrile(3331-60-0)

Safety Data

• Hazardous Substances Data: 3331-60-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 165, 1948 DOI: 10.1021/ja01181a048

InChI:InChI=1/C4H6ClN/c1-4(2,5)3-6/h1-2H3

Upstream product

• 78-82-0 Isobutyronitrile 
• 7462-75-1 dimethylcarbamylmethyl chloride 
• 18537-69-4 2-chloro-2-methyl-propionaldehyde oxime 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 6092-34-8 α,α,β-Trichlor-N-trichlorphosphoranyliden-isobutylamin 
• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 10026-13-8 phosphorus pentachloride 
• 71-43-2 benzene 
• 7782-50-5 chlorine 
• 107-06-2 1,2-dichloro-ethane 
• 79-39-0 Methacrylamide 

Downstream Products

• 22421-97-2 methyl 2-chloroisobutyrate 
• 126-98-7 methacrylonitrile 

Relevant articles and documents

C(sp3)-H Fluorination with a Copper(II)/(III) Redox Couple

Despite the growing interest in the synthesis of fluorinated organic compounds, few reactions are able to incorporate fluoride ions directly into alkyl C-H bonds. Here, we report the C(sp3)-H fluorination reactivity of a formally copper(III) fluoride complex. The C-H fluorination intermediate, LCuF, along with its chloride and bromide analogues, LCuCl and LCuBr, were prepared directly from halide sources with a chemical oxidant and fully characterized with single-crystal X-ray diffraction, X-ray absorption spectroscopy, UV-vis spectroscopy, and 1H nuclear magnetic resonance spectroscopy. Quantum chemical calculations reveal significant halide radical character for all complexes, suggesting their ability to initiate and terminate a C(sp3)-H halogenation sequence by sequential hydrogen atom abstraction (HAA) and radical capture. The capability of HAA by the formally copper(III) halide complexes was explored with 9,10-dihydroanthracene, revealing that LCuF exhibits rates 2 orders of magnitude higher than LCuCl and LCuBr. In contrast, all three complexes efficiently capture carbon radicals to afford C(sp3)-halogen bonds. Mechanistic investigation of radical capture with a triphenylmethyl radical revealed that LCuF proceeds through a concerted mechanism, while LCuCl and LCuBr follow a stepwise electron transfer-halide transfer pathway. The capability of LCuF to perform both hydrogen atom abstraction and radical capture was leveraged to enable fluorination of allylic and benzylic C-H bonds and α-C-H bonds of ethers at room temperature.

The Decomposition of Azobisisobutyronitrile under the Conditions of Free-radical Chlorinaton

The kinetics of the decomposition of azobisiobutyronitrile in the 1,2-dichloroethane-carbon tetrachloride-chlorine system have been investigated and it is shown that, in free-radical chlorination, there is competition between the chain and unimolecular mechanisms of the decomposition of azobisiobutyronitrile.

Synthesis of alpha-amino acids

A method for synthesizing alpha amino acids proceding through novel intermediates of the formulas: wherein R1 and R2 are each selected from hydrogen monovalent substituted and unsubstituted hydrocarbon radicals of 1 to 10 carbon atoms. The use of these intermediates allows the synthesis steps to be exothermic and results in an overall synthesis method which is faster than the snythesis methods of the prior art.