2-Chloroacrylonitrile
[CAS# 920-37-6]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 2-Chloroacrylonitrile
• Synonyms: alpha-Chloroacrylonitrile
• Molecular Formula: C₃H₂ClN
• Molecular Weight: 87.51
• CAS Registry Number: 920-37-6
• EC Number: 213-055-2
• SMILES: C=C(C#N)Cl

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Melting point: -65 °C
• Index of Refraction: 1.435, Calc.^*
• Boiling Point: 89.5±13.0 °C (760 mmHg), Calc.^*
• Flash Point: 6.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS08;GHS05;GHS09 Danger
• Risk Statements: H225-H300-H301-H310-H311-H314-H330-H334-H350-H400
• Safety Statements: P203-P210-P233-P240-P241-P242-P243-P260-P262-P264-P270-P271-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P318-P320-P321-P330-P342+P316-P361+P364-P363-P370+P378-P391-P403-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Carcinogenicity	Carc.	1B	H350
Acute toxicity	Acute Tox.	2	H300
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	1	H300
Carcinogenicity	Carc.	2	H351

• Transport Information: UN 3273

Discovery and Applications

2-Chloroacrylonitrile, with the chemical formula C3H2ClN, is an organic compound containing both a nitrile and a chloro group. It is typically produced by the chlorination of acrylonitrile, a process that has been known and used in industrial settings for several decades. 2-Chloroacrylonitrile is a colorless to pale yellow liquid with a pungent odor and is a reactive intermediate in organic synthesis.

The primary application of 2-chloroacrylonitrile is in the synthesis of other chemicals, particularly in the production of various specialty polymers and agrochemicals. Its reactivity due to the presence of both a nitrile and a chlorine atom makes it an important intermediate in the formation of other organic compounds.

In the chemical industry, 2-chloroacrylonitrile is used in the preparation of substituted acrylic compounds. These can be employed in a variety of polymerization processes, leading to the synthesis of specialty resins, coatings, and adhesives. The compound is a key intermediate in the production of acrylonitrile-butadiene-styrene (ABS) copolymers, which are widely used in engineering plastics. Its role in such applications is crucial due to its ability to form functionalized monomers that can be further polymerized to achieve desired properties.

In the pharmaceutical and agricultural industries, 2-chloroacrylonitrile has been explored for its potential as a precursor to bioactive compounds. Its structure makes it suitable for modifications leading to compounds with biological activities, such as potential herbicides and fungicides. This ability to modify and synthesize new chemicals for plant protection is a key area of its use.

The compound also finds its applications in the production of various intermediates used in the manufacturing of dyes, pesticides, and other fine chemicals. Its role as a building block in these sectors is vital, particularly due to its ease of functionalization and the availability of its synthetic routes.

While 2-chloroacrylonitrile is useful in various industrial processes, it is also considered hazardous. It is toxic if inhaled, ingested, or absorbed through the skin. Its handling requires appropriate safety precautions to prevent exposure, and it is classified as a hazardous material under various safety regulations.

In summary, 2-chloroacrylonitrile is a versatile chemical compound with applications primarily in the production of specialty chemicals, polymers, and agrochemicals. Its role as an intermediate in chemical synthesis underscores its importance in industrial chemistry. The compound’s utility in manufacturing a variety of functionalized chemicals continues to make it valuable in different sectors, though its toxicity necessitates careful handling.

References

1975. Reaction of α-chloroacrylonitrile with hydrazines. Chemistry of Heterocyclic Compounds, 11(2).
DOI: 10.1007/bf00471402

2013. Synthesis of bis-heterocyclic compounds with a phenylene bridge from 1,4- and 1,3-bis(2-chloro-2-cyanovinyl)benzenes. Chemistry of Heterocyclic Compounds, 49(6).
DOI: 10.1007/s10593-013-1325-y

2022. Current Advances in Meerwein-type Radical Alkene Functionalizations. Synthesis, 54(22).
DOI: 10.1055/s-0040-1719893