920-37-6

Basic information

• Product Name: 2-Chloroacrylonitrile
• Synonyms: 1-Chloroaerylonitrile;2-CHLORACRYLONITRIL;2-CHLOROACRYLONITRILE;2-CHLOROCYANOETHYLENE;2-CHLOROACRYLONITRILE, STAB.;2-Chloroacrylonitrile, stabilized, 99%;2-PROPENONITRLLE;2-Chloroacrylonitrile (stabilized with HQ)
• CAS NO: 920-37-6
• Molecular Formula: C3H2ClN
• Molecular Weight: 87.51
• EINECS: 213-055-2
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Aliphatics;Nitriles;C1 to C5;Cyanides/Nitriles;Nitrogen Compounds;Miscellaneous Reagents;Building Blocks;C1 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 920-37-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: −65 °C(lit.)
• Boiling Point: 88-89 °C(lit.)
• Flash Point: 44 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.096 g/mL at 25 °C(lit.)
• Vapor Pressure: 58.4mmHg at 25°C
• Refractive Index: n20/D 1.429(lit.)
• Storage Temp.: Flammables area
• Solubility: Chloroform, Ethyl Acetate, Methanol (Very Slightly)
• BRN: 773744
• CAS DataBase Reference: 2-Chloroacrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroacrylonitrile(920-37-6)
• EPA Substance Registry System: 2-Chloroacrylonitrile(920-37-6)

Safety Data

• 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
• RIDADR: UN 3383 6.1/PG 1
• WGK Germany: 3
• RTECS: AT5525000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 920-37-6(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 920-37-6 differently. You can refer to the following data:
1. Common reagent in cycloaddition reactions.1,2
2. 2-Chloroacrylonitrile (cas# 920-37-6) is a compound useful in organic synthesis.

General Description

A liquid. Boiling point 190-192°F (88-89°C). Density 1.096 g / cm3. Flash point 44°F. Highly toxic.

Reactivity Profile

2-Chloroacrylonitrile readily polymerizes, and copolymerizes with other unsaturated monomers .

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Suspected carcinogen. Poison by intravenous route. A powerful irritant. A dangerous fire hazard when exposed to heat or flame. To fight fire, use water, dry chemical, CO2, foam. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and CN-. See also NITRILES.

InChI:InChI=1/C3H2ClN/c1-3(4)2-5/h1H2

Synthetic route

Conditions	Yield
In dimethyl sulfoxide at 80℃; for 24h;	86%
With methanol; sodium acetate
With sulfuric acid
With toluene-4-sulfonic acid
With di(2-ethylhexyl)amine hydrochloride

Conditions	Yield
With hydroquinone; 2-Chloroacrylonitrile In toluene at 0℃; Heating;	77%

+ trans-β-chloroacrylonitrile (871-29-4, 3721-37-7, 3721-38-8) + 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
at 540℃;	A n/a B n/a C 28%
at 540℃;

2,2,3-trichloropropionitrile (813-74-1) → 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
With dibutyl ether; magnesium; hydroquinone; magnesium iodide at 150℃;

acrylonitrile (107-13-1) → 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
With chlorine; pyrographite at 300℃;
In sodium bicarbonate

potassium cyanide (151-50-8) + 2,3-dichloropropionitrile (2601-89-0) → 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
With chloroform

(2-Chlor-2-cyan-ethyl)-(4-nitro-phenyl)-sulfid (90272-99-4) → para-nitrobenzenethiol (1849-36-1) + 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
Trimethylenediamine In water; dimethyl sulfoxide at 25℃; Rate constant; elimination;
In water-d2; dimethyl sulfoxide at 25℃; Rate constant; 1,3-diaminopropane buffer, elimination;

C10H10ClN2O2S(1+)*BF4(1-) → 1-methylthio-4-nitro-benzene (701-57-5) + 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
With potassium chloride; 1,3-propanediamine*H+ In water at 25℃; Rate constant; Mechanism; var. primary amines and hydroxide anion; effect of catalyst basicity and leaving group basicity on the rate;

C9H6(2)HClN2O2S → C6H4(2)HNO2S + 2-Chloroacrylonitrile (920-37-6)

Conditions	Yield
In water; dimethyl sulfoxide at 25℃; Rate constant; 1,3-diaminopropane buffer, elimination;

Upstream product

• 107-13-1 acrylonitrile 
• 151-50-8 potassium cyanide 
• 2601-89-0 2,3-dichloropropionitrile 
• 90272-99-4 (2-Chlor-2-cyan-ethyl)-(4-nitro-phenyl)-sulfid 
• 7782-50-5 chlorine 
• 67-66-3 chloroform 
• 123-31-9 hydroquinone 
• 40672-22-8 1-methoxy-3,4,5-trimethyl-1,4-cyclohexadiene 
• 6702-21-2 2-acetoxy-3-chloropropanenitrile 
• 813-74-1 2,2,3-trichloropropionitrile 

Downstream Products

• 100062-16-6 N-(2-chloro-2-cyano-ethyl)-phthalamic acid methyl ester 
• 764-42-1 butenedinitrile 
• 24064-11-7 3ξ-benzylsulfanyl-acrylonitrile 
• 108384-24-3 chloro-2 thiobenzyl-3 propionitrile 
• 1012-24-4 2-chloro-3-(4-chloro-phenylsulfanyl)-propionitrile 
• 91085-93-7 2-chloro-3-pentachlorophenylsulfanyl-propionitrile 
• 108127-69-1 2-chloro-3-cyclohexylmercapto-propionitrile 
• 54746-86-0 2-chloro-3-(4-methoxy-phenylsulfanyl)-propionitrile 
• 764-42-1 1,2-Dicyanoethylene 
• 99359-88-3 3-benzyloxy-2-chloro-propionic acid amide 
• 16490-68-9 2-chloroacrylamide 
• 813-74-1 2,2,3-trichloropropionitrile 
• 90418-08-9 2,2-Dichlor-3-<4-nitro-phenyl>-propionitril 
• 30242-55-8 2,2-Dichlor-3-<2-nitro-phenyl>-propionitril 

Relevant articles and documents

Preparation of α-haloacrylate derivatives via dimethyl sulfoxide-mediated selective dehydrohalogenation

(Chemical Equation Presented) Dimethyl sulfoxide causes α/β-dihalopropanoate derivatives to undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles. Synthesis of these molecules has been reported in the literature to be difficult. Among all the existing dehydrohalogenation procedures, this protocol is the most facile, practical, and environmentally benign process.

Thienylpyrrole fungicidal agents

There are provided fungicidal thienyl- and furylpyrrole compounds of formula I STR1 Further provided are compositions and methods comprising those compounds for the protection of plants from fungal infestation and disease.

Elimination reactions: Experimental confirmation of the predicted elimination of (β-cyanoethyl)sulfonium ions through a concerted, E2 mechanism

Extrapolation of the lifetimes of carbanion intermediates formed in the elimination reactions of a series of β-cyanoethyl thioethers with different leaving groups (J. Am. Chem. Soc. 1988, 110, 5087-5095) predicts that the carbanions will not have a significant lifetime for pKlg a 2SO/H2O, 25.0 °C). Values of βlg obtained from Br?nsted-type plots of log kB against the estimated pKa values of the leaving groups, decrease from 0.39 to 0.24 with increasing pKa of the base catalyst. The changes in β and βlg are described by the interaction coefficient pxy=d?βlg/?pK BH=?βlg/?KBH=0.026. The deuterium isotope effect for proton removal from Ph-S+(Me)-CH2CL2CN is kH/kD=4.4 and 4.9 for tris(hydroxymethyl)aminomethane and ethylamine buffers, respectively, and there is no detectable protium exchange into the deuterated substrate. The positive pxy coefficient provides evidence for coupling between proton abstraction and leaving group expulsion; it confirms the concerted AxhDHDN (E2) mechanism. The values of β and βlg indicate an imbalance in the transition state, in which proton transfer is ahead of leaving group expulsion. The change from a stepwise AxhDHH+DNN (ElcB) mechanism for thiophenoxide leaving groups to a concerted mechanism for sulfide leaving groups is consistent with the notion that the mechanism is determined solely by the lifetime of the carbanion; there is no evidence for the coexistence of stepwise and concerted mechanisms.