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 a highly reactive acyl chloride compound with strong corrosive properties and significant toxicological hazards. This colorless to pale yellow liquid serves as a crucial intermediate in organic synthesis and pharmaceutical manufacturing. With its molecular formula C2H2Cl2O and molecular weight of 112.94 g/mol, 2-chloroacetyl chloride belongs to the family of halogenated acyl chlorides, compounds known for their exceptional reactivity toward nucleophiles. The presence of both chloroacetyl and chloride functional groups makes this substance particularly valuable in synthetic chemistry, where it acts as an effective acylating agent. The compound's classification under multiple acute toxicity categories (Acute Tox. 3) across different exposure routes, combined with its skin corrosion potential (Skin Corr. 1A) and specific target organ toxicity (STOT RE 1), necessitates stringent handling protocols. Its GHS pictograms include skull and crossbones (GHS06), health hazard (GHS08), corrosion (GHS05), and environmental hazard (GHS09), reflecting its comprehensive risk profile. The ADR classification of 6.1 indicates its status as a toxic substance requiring specialized transportation procedures. Primary industrial applications include the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals where chloroacetyl functionality is required. It serves as a key building block in manufacturing various therapeutic compounds and serves similar synthetic roles to related halogenated compounds like 2-chloroacetaldehyde in specific chemical transformations. The compound's reactivity also makes it valuable in producing chloroacetamide derivatives and other nitrogen-containing pharmaceuticals. OYSI maintains reliable supply chains for 2-chloroacetyl chloride to support European chemical manufacturing operations.

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 organic chemical compound with the molecular formula C2H2Cl2O and CAS number 79-04-9. This acyl halide derivative serves as an important intermediate in organic synthesis and pharmaceutical manufacturing. With a molecular weight of 112.94 g/mol, it belongs to the family of chlorinated acetyl compounds and exhibits strong reactivity due to its dual chlorine functionality, making it valuable for various chemical transformations and industrial applications.

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, irritating odor. It has high reactivity with water and alcohols, leading to rapid hydrolysis. The compound is miscible with most organic solvents but reacts violently with water, releasing hydrogen chloride gas. Its boiling point is around 106°C, and it has a density higher than water. Due to its acyl chloride nature, it readily undergoes nucleophilic substitution reactions.

What is 2-chloroacetyl chloride used for?

2-chloroacetyl chloride is primarily used as a key intermediate in pharmaceutical synthesis, particularly for manufacturing antibiotics and other therapeutic compounds. It serves as an acylating agent in organic chemistry for introducing chloroacetyl groups into molecules. The compound finds applications in the production of agrochemicals, dyes, and specialty chemicals. It is also utilized in research laboratories for peptide synthesis and as a building block for various heterocyclic compounds in medicinal chemistry.

How to handle 2-chloroacetyl chloride safely?

2-chloroacetyl chloride requires extreme caution during handling 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 to prevent inhalation exposure. Avoid contact with skin, eyes, and respiratory system. Use appropriate tools to prevent spills and ensure emergency shower and eyewash stations are readily accessible. All personnel must be trained in proper handling procedures.

How to store 2-chloroacetyl chloride correctly?

2-chloroacetyl chloride must be stored in tightly sealed, corrosion-resistant containers in a cool, dry, well-ventilated area away from heat sources and direct sunlight. Keep strictly separated from water, alcohols, amines, and other nucleophiles to prevent violent reactions. Storage areas should be equipped with appropriate spill containment and ventilation systems. Containers must be properly labeled and stored in secondary containment. Regular inspection for container integrity is essential due to the compound's corrosive properties.

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

Immediate action is critical upon contact with 2-chloroacetyl chloride. For skin contact, remove contaminated clothing and flush affected area with copious amounts of water for at least 15 minutes. In case of eye contact, rinse immediately with water for 15-20 minutes and remove contact lenses if present. If inhaled, move to fresh air immediately. For ingestion, do not induce vomiting and rinse mouth with water. Seek immediate medical attention in all cases and provide safety data sheet to medical personnel.

How to dispose of 2-chloroacetyl chloride properly?

2-chloroacetyl chloride disposal must comply with local and national hazardous waste regulations as it is classified as toxic and corrosive waste. Small quantities can be carefully hydrolyzed under controlled conditions by trained personnel, neutralizing the resulting hydrochloric acid. Larger quantities require disposal through licensed hazardous waste contractors. Never dispose of in sewers, drains, or regular waste streams. All disposal activities must be documented and performed according to applicable environmental regulations and safety protocols.

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 conditions. It must be packaged in UN-approved containers with appropriate labels and placards displaying the toxic hazard symbol. Transport vehicles require proper ventilation and emergency equipment. Drivers must hold ADR certification and carry transport documents including safety data sheets. Shipments must comply with quantity limitations and routing restrictions as specified in dangerous goods regulations.

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 obligations. It carries multiple hazard classifications including acute toxicity, skin corrosion, and aquatic toxicity, requiring proper labeling with GHS pictograms and safety data sheets. The compound may be subject to import/export licensing requirements and workplace exposure limits. Users must comply with occupational health regulations and may need permits for handling significant quantities in industrial applications.

Where to buy 2-chloroacetyl chloride in Europe?

2-chloroacetyl chloride is available through OYSI, a specialized European distributor of technical chemicals serving industrial and research customers across Europe. OYSI provides high-quality chemical products with full regulatory compliance including proper documentation, safety data sheets, and transport arrangements. As a professional chemical supplier, OYSI ensures reliable supply chain management and technical support for customers requiring this specialized reagent for pharmaceutical, research, or industrial applications throughout European markets.

Data Sources

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