2-chloroacetyl chloride

C2H2Cl2O

CAS79-04-9
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
GHS05 Gefahrensymbol: Ätzend – Ätzwirkung
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
Danger

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Identification

CAS Number
79-04-9
EC Number
201-171-6
UN Number
1752
Index Number
607-080-00-1
PubChem CID
6577

Physical-chemical properties

Molecular Formula
C2H2Cl2O
Molar Mass
112.94 g/mol
IUPAC Name
2-chloroacetyl chloride

Chemical Identifiers

InChI
InChI=1S/C2H2Cl2O/c3-1-2(4)5/h1H2
InChI Key
VGCXGMAHQTYDJK-UHFFFAOYSA-N

Overview

2-chloroacetyl chloride (CAS 79-04-9) is an acyl chloride compound with highly reactive carbonyl functionality and significant corrosive properties. This versatile chemical intermediate plays a crucial role in organic synthesis and industrial manufacturing processes. As a bifunctional molecule containing both chloroacetyl and chloride groups, 2-chloroacetyl chloride exhibits exceptional reactivity toward nucleophiles, making it an invaluable building block for pharmaceutical intermediates, agrochemicals, and specialty chemicals. The compound's molecular structure (C2H2Cl2O) features an electrophilic carbonyl carbon that readily undergoes nucleophilic substitution reactions, while the alpha-chloro substituent provides additional synthetic versatility through displacement reactions. Due to its highly reactive nature, 2-chloroacetyl chloride requires careful handling protocols. Classified under multiple acute toxicity categories and as a skin corrosive substance (Skin Corr. 1A), it demands stringent safety measures including appropriate personal protective equipment and controlled storage conditions. The compound's classification under ADR Class 6.1 reflects its toxic properties, while its aquatic acute toxicity rating emphasizes the need for environmental protection measures during handling and disposal. In industrial applications, 2-chloroacetyl chloride serves primarily as a synthetic intermediate in pharmaceutical manufacturing, particularly for producing chloroacetamide derivatives and heterocyclic compounds. It finds additional use in the synthesis of pesticides and herbicides, where its reactivity enables the formation of biologically active molecules. Similar to related compounds like 2-chloroacetaldehyde, it participates in multi-step synthetic pathways requiring precise reaction control. OYSI provides reliable access to 2-chloroacetyl chloride with comprehensive technical support and regulatory documentation to meet European industrial requirements.

Safety & Classification

Danger
Classification:

Acute Tox. 3 *; Acute Tox. 3 *; Acute Tox. 3 *; STOT RE 1; Skin Corr. 1A; Aquatic Acute 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H331

Toxic if inhaled.

H311

Toxic in contact with skin.

H301

Toxic if swallowed.

H372

Causes damage to organs through prolonged or repeated exposure.

H314

Causes severe skin burns and eye damage.

H400

Very toxic to aquatic life.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Toxic

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Toxic

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Eye Contact

Harmful

Measures if substance gets into the eyes

First Aid Actions

  • +P305IF IN EYES:
  • +P351Rinse cautiously with water for several minutes.
  • +P338Remove contact lenses, if present and easy to do. Continue rinsing.
  • +P313Get medical advice/attention.

Related hazard statements:

Ingestion

Toxic

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number1752
ADR Class6.1
Packing GroupI
Tunnel CodeC/D
Proper Shipping NameChloracetylchlorid
Marine PollutantNo

Frequently Asked Questions

What is 2-chloroacetyl chloride?

2-chloroacetyl chloride is a highly reactive organochlorine compound with the molecular formula C2H2Cl2O and CAS number 79-04-9. This acyl chloride derivative features both chlorine substituents that make it extremely reactive towards nucleophiles. With a molecular weight of 112.94 g/mol, it serves as an important intermediate in organic synthesis and chemical manufacturing processes requiring controlled chloroacetylation reactions.

What are the physicochemical properties of 2-chloroacetyl chloride?

2-chloroacetyl chloride is a colorless to pale yellow liquid at room temperature with a pungent, acrid odor. It has a boiling point around 105-106°C and readily hydrolyzes in water, releasing hydrogen chloride gas. The compound is highly reactive and corrosive, soluble in organic solvents like benzene and ether but violently reacts with protic solvents, making proper handling essential for safe use.

What is 2-chloroacetyl chloride used for?

2-chloroacetyl chloride is primarily used as an acylating agent in organic synthesis for introducing chloroacetyl groups into molecules. It serves as a key intermediate in pharmaceutical manufacturing, agrochemical production, and fine chemical synthesis. The compound is particularly valuable in producing chloroacetamides, esters, and other derivatives used in drug development, pesticide formulation, and specialty chemical manufacturing requiring controlled chlorination reactions.

How to handle 2-chloroacetyl chloride safely?

2-chloroacetyl chloride requires strict safety measures due to its corrosive and toxic nature. Essential PPE includes chemical-resistant gloves, safety goggles, face shield, and full protective clothing. Work must be conducted in a well-ventilated fume hood with emergency eyewash stations nearby. Avoid contact with skin, eyes, and respiratory system. Use only non-metallic, dry equipment as the compound reacts violently with water and corrodes metals.

How to store 2-chloroacetyl chloride correctly?

2-chloroacetyl chloride must be stored in tightly sealed containers made of compatible materials like glass or PTFE-lined vessels in a cool, dry, well-ventilated area away from heat sources. Keep strictly away from water, alcohols, amines, and metals which can cause violent reactions. Storage areas should maintain temperatures below 25°C and be equipped with appropriate spill containment measures and corrosion-resistant surfaces.

What to do in case of contact with 2-chloroacetyl chloride?

2-chloroacetyl chloride contact requires immediate emergency response due to its corrosive nature. For skin contact, immediately remove contaminated clothing and flush with copious amounts of water for at least 15 minutes. For eye exposure, rinse immediately with water for 15+ minutes and seek medical attention. If inhaled, move to fresh air immediately. For ingestion, do not induce vomiting and seek immediate medical care. Always contact emergency services for serious exposures.

How to properly dispose of 2-chloroacetyl chloride?

2-chloroacetyl chloride disposal requires specialized hazardous waste procedures due to its toxic and corrosive classification. The compound cannot be disposed of through regular waste streams and must be handled by licensed hazardous waste contractors. Small quantities may be carefully hydrolyzed under controlled conditions by trained personnel, but this generates corrosive byproducts requiring neutralization. Always consult local environmental regulations and waste disposal experts for proper handling.

How to transport 2-chloroacetyl chloride?

2-chloroacetyl chloride is classified under ADR as Class 6.1 (toxic substances) Packing Group I, indicating high toxicity requiring stringent transport protocols. Packages must meet UN specification standards for toxic liquids with appropriate hazard labels including GHS06, GHS05, GHS08, and GHS09 pictograms. Transport requires specialized vehicles, trained drivers, and emergency response documentation. Only authorized carriers experienced in hazardous chemical transport should handle shipments.

Is 2-chloroacetyl chloride subject to specific regulations?

2-chloroacetyl chloride is subject to comprehensive chemical regulations including REACH registration requirements in Europe and CLP classification as Acute Tox. 3, STOT RE 1, Skin Corr. 1A, and Aquatic Acute 1. While not currently listed as an SVHC, its multiple hazard classifications require strict compliance with occupational safety standards, environmental protection measures, and proper documentation for commercial use, handling, and distribution throughout the supply chain.

Where to buy 2-chloroacetyl chloride in Europe?

2-chloroacetyl chloride is available through specialized chemical distributors in Europe, including OYSI, which serves as a reliable supplier for industrial and research applications. Due to its hazardous classification and regulatory requirements, procurement requires proper documentation, safety protocols, and compliance with local regulations. Professional chemical distributors like OYSI ensure proper handling, packaging, and delivery while maintaining regulatory compliance throughout the European market.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.