Chloroacetyl chloride
[CAS# 79-04-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Acid halide
• Name: Chloroacetyl chloride
• Synonyms: Chloroacetic ahloride; Chloroacetylchloride; Monochloroacetyl chloride
• Molecular Formula: C₂H₂Cl₂O
• Molecular Weight: 112.94
• CAS Registry Number: 79-04-9
• EC Number: 201-171-6
• SMILES: C(C(=O)Cl)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.418 g/mL (Expl.)
• Melting point: -22 °C (Expl.)
• Index of Refraction: 1.43, Calc.^*, 1.453 (Expl.)
• Boiling Point: 106.0 °C (760 mmHg), Calc.^*, 105-106 °C (Expl.)
• Flash Point: 34.0±20.2 °C, Calc.^*, 100 °C (Expl.)
• Water solubility: reacts

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

Safety Data

• Hazard Symbols: GHS06;GHS08;GHS05;GHS09 Danger
• Risk Statements: H290-H301-H310-H311-H314-H318-H331-H372-H400-H410
• Safety Statements: P234-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P321-P330-P361+P364-P363-P390-P391-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin corrosion	Skin Corr.	1A	H314
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	3	H311
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute toxicity	Acute Tox.	2	H310
Specific target organ toxicity - repeated exposure	STOT RE	2	H372
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 1752

Discovery and Applications

Chloroacetyl chloride (C2H3ClO) is an organic compound that consists of a chloro group (Cl) attached to an acetyl group (COCH3). It is a colorless, corrosive liquid with a pungent odor and is highly reactive, particularly with water, which it hydrolyzes to form acetic acid and hydrogen chloride. Chloroacetyl chloride is used in a variety of chemical syntheses and industrial applications.

The discovery of chloroacetyl chloride is linked to the development of acyl chloride chemistry in the late 19th and early 20th centuries. Acyl chlorides, including chloroacetyl chloride, were found to be useful intermediates in organic synthesis due to their ability to react with nucleophiles, such as amines, alcohols, and thiols, forming derivatives like amides, esters, and thioesters. This reactivity made chloroacetyl chloride a valuable reagent in both laboratory and industrial settings.

One of the primary applications of chloroacetyl chloride is in the synthesis of pharmaceuticals. It is used to manufacture certain drugs, including those used in cancer treatment, by acting as an acylating agent to introduce the acetyl group into organic molecules. For example, chloroacetyl chloride can be used in the preparation of acetylated derivatives of amino acids and peptides, which are important components of many pharmaceutical compounds.

Chloroacetyl chloride is also utilized in the production of agrochemicals, where it is involved in the synthesis of herbicides and insecticides. Its ability to react with various compounds makes it an effective intermediate in the formation of complex organic molecules used for pest control. Furthermore, it is employed in the manufacture of specialty chemicals, such as plasticizers and surfactants, which are used in a wide range of applications from coatings to detergents.

In the polymer industry, chloroacetyl chloride is used as a starting material for the synthesis of various polymers, including those used in coatings, adhesives, and plastics. It can be used to modify polymer chains, enhancing the properties of the final product. Additionally, it is sometimes used as a reagent in the preparation of functionalized materials with specific chemical properties.

Chloroacetyl chloride is highly reactive and must be handled with care. It is a strong irritant to the skin, eyes, and respiratory system, and exposure can cause severe chemical burns. It should be stored in tightly sealed containers in cool, dry conditions, away from moisture and incompatible materials. Safety precautions, including wearing appropriate protective gear such as gloves, goggles, and a lab coat, are necessary when handling this compound.

In summary, chloroacetyl chloride is an important chemical intermediate used in a wide range of applications, including pharmaceuticals, agrochemicals, and polymer production. Its reactivity makes it a valuable reagent in organic synthesis, enabling the preparation of a variety of functionalized compounds. However, its corrosive nature requires careful handling and adherence to safety protocols.

References

2013. The synthesis and biological testing of bacilysin analogues. Amino Acids, 45(5).
DOI: 10.1007/s00726-013-1571-4

2017. Synthesis, characterization, biological evaluation and molecular docking studies of 2-(1H-benzo[d]imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides. Chemistry Central Journal, 11(1).
DOI: 10.1186/s13065-017-0312-2

2018. Trace level determination of chloroacetyl chloride and degradation products by derivatization gas chromatography. Journal of Pharmaceutical and Biomedical Analysis, 149.
DOI: 10.1016/j.jpba.2017.09.026