2,2,2-trifluoroacetyl chloride

C2ClF3O

CAS354-32-5

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Identification

CAS Number
354-32-5
EC Number
206-556-2
UN Number
3057
PubChem CID
61106

Physical-chemical properties

Molecular Formula
C2ClF3O
Molar Mass
132.47 g/mol
IUPAC Name
2,2,2-trifluoroacetyl chloride

Chemical Identifiers

InChI
InChI=1S/C2ClF3O/c3-1(7)2(4,5)6
InChI Key
PNQBEPDZQUOCNY-UHFFFAOYSA-N

Overview

2,2,2-Trifluoroacetyl chloride (CAS 354-32-5) is a highly reactive acyl halide compound with strong electrophilic properties and exceptional chemical stability due to its trifluoromethyl group. This specialized organofluorine compound represents a critical building block in advanced chemical synthesis, particularly valued for its unique reactivity profile and the electron-withdrawing effects of its three fluorine atoms. With the molecular formula C2ClF3O and a molecular weight of 132.47 g/mol, 2,2,2-trifluoroacetyl chloride serves as an essential reagent in pharmaceutical, agrochemical, and specialty chemical manufacturing processes. The compound's structure features a carbonyl group bonded to both a chlorine atom and a trifluoromethyl group, creating a highly electrophilic center that readily undergoes nucleophilic acyl substitution reactions. This reactivity makes it particularly useful for introducing trifluoroacetyl protecting groups in organic synthesis, where the electron-withdrawing nature of the fluorine atoms provides enhanced stability compared to conventional acetyl derivatives. Unlike simpler compounds such as nitrous oxide, which serves primarily as an oxidizing agent, trifluoroacetyl chloride offers precise synthetic control for complex molecular transformations. The compound's classification under ADR Class 2 reflects its gaseous nature and associated handling requirements. Industrial applications include the synthesis of trifluoroacetamide derivatives, pharmaceutical intermediates, and specialized fluorinated compounds used in materials science. It also plays a crucial role in peptide chemistry as a protecting group reagent and in the production of agrochemical active ingredients. OYSI provides 2,2,2-trifluoroacetyl chloride to European customers, ensuring reliable supply for demanding synthetic applications across pharmaceutical, chemical, and research sectors.

Safety & Classification

No Hazard Classification

This substance is not classified as hazardous according to CLP Regulation (EC) No 1272/2008.

Transport (ADR)

UN Number3057
ADR Class2
Packing Group
Tunnel CodeC/D
Proper Shipping NameTrifluoracetylchlorid, unter Druck verflüssigt
Marine PollutantNo

Frequently Asked Questions

What is 2,2,2-trifluoroacetyl chloride?

2,2,2-trifluoroacetyl chloride is an organofluorine acyl chloride compound with the molecular formula C2ClF3O and CAS number 354-32-5. This chemical features three fluorine atoms attached to the acetyl group, making it a highly reactive fluorinated derivative. With a molecular weight of 132.47 g/mol, it serves as an important building block in organic synthesis and pharmaceutical chemistry due to its unique trifluoromethyl functionality.

What are the physicochemical properties of 2,2,2-trifluoroacetyl chloride?

2,2,2-trifluoroacetyl chloride is a colorless liquid with a pungent, acrid odor typical of acyl chlorides. It has a boiling point around 39-40°C and is highly reactive with water, undergoing rapid hydrolysis to form trifluoroacetic acid and hydrogen chloride. The compound is miscible with most organic solvents but reacts violently with protic solvents. Its high electronegativity due to fluorine atoms makes it particularly reactive toward nucleophiles.

What is 2,2,2-trifluoroacetyl chloride used for?

2,2,2-trifluoroacetyl chloride is primarily used as an acylating agent in organic synthesis to introduce trifluoroacetyl groups into molecules. It serves as a key intermediate in pharmaceutical manufacturing, particularly for synthesizing fluorinated drugs and active pharmaceutical ingredients. The compound is also utilized in the production of agrochemicals, specialty polymers, and fluorinated materials. Its reactivity makes it valuable for creating protecting groups in peptide synthesis and other advanced chemical processes.

How to handle 2,2,2-trifluoroacetyl chloride safely?

2,2,2-trifluoroacetyl chloride requires careful handling due to its highly reactive nature and corrosive properties. Always wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and lab coats. Work in a well-ventilated fume hood to avoid inhalation of vapors. Use dry, inert atmosphere conditions as the compound reacts violently with moisture. Ensure all equipment is completely dry before use and have neutralizing agents readily available for spills.

How to store 2,2,2-trifluoroacetyl chloride correctly?

2,2,2-trifluoroacetyl chloride must be stored in tightly sealed, moisture-proof containers under anhydrous conditions to prevent hydrolysis. Keep containers in a cool, dry place away from heat sources and direct sunlight. Store separately from water, alcohols, amines, and other nucleophilic compounds that can react violently. Use amber glass bottles or other suitable chemical-resistant containers. Maintain storage temperature below 25°C and ensure adequate ventilation in storage areas.

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

2,2,2-trifluoroacetyl chloride contact requires immediate emergency response due to its corrosive nature. For skin contact, immediately remove contaminated clothing and flush affected area with copious amounts of water for at least 15 minutes. In case of eye contact, rinse thoroughly with water and seek immediate medical attention. If inhaled, move to fresh air immediately. For ingestion, do not induce vomiting and seek emergency medical care. Always consult safety data sheets for specific first aid measures.

How to dispose of 2,2,2-trifluoroacetyl chloride properly?

2,2,2-trifluoroacetyl chloride disposal must follow strict hazardous waste regulations and local environmental guidelines. The compound should never be poured down drains or disposed of with regular waste. Carefully neutralize small quantities under controlled conditions using appropriate basic solutions, then dispose of neutralized waste according to local regulations. For larger quantities, contact licensed hazardous waste disposal companies. Always document disposal procedures and maintain proper waste tracking records as required by regulations.

How to transport 2,2,2-trifluoroacetyl chloride?

2,2,2-trifluoroacetyl chloride is classified under ADR Class 2, indicating it falls under gases or gas-related hazardous materials for transport purposes. The compound must be shipped in appropriate UN-specification packaging designed for corrosive and reactive chemicals. Proper hazard labels and documentation are required during transport. Vehicles must be equipped with appropriate emergency equipment, and drivers need proper training for handling dangerous goods. Always consult current ADR regulations for specific transport requirements and restrictions.

Is 2,2,2-trifluoroacetyl chloride subject to specific regulations?

2,2,2-trifluoroacetyl chloride is subject to various chemical regulations including REACH registration requirements for import and use in the European Union. The compound is not currently listed as a Substance of Very High Concern (SVHC). However, it may be subject to workplace safety regulations due to its reactive and corrosive nature. Users must comply with local occupational health and safety standards, proper labeling requirements, and maintain safety data sheets as mandated by CLP regulation.

Where to buy 2,2,2-trifluoroacetyl chloride in Europe?

2,2,2-trifluoroacetyl chloride is available through OYSI, a trusted European distributor of specialty chemicals and industrial compounds. OYSI provides reliable supply chains across Europe, ensuring proper handling and documentation for this reactive chemical. As a professional chemical distributor, OYSI maintains appropriate storage conditions and regulatory compliance. Contact OYSI directly for availability, technical specifications, and delivery options to your location. Professional customers can rely on OYSI's expertise in handling specialty fluorinated compounds.

Data Sources

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