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 fluorinated acyl chloride with highly reactive carbonyl chloride functionality and strong electron-withdrawing trifluoromethyl properties. This specialized organofluorine compound serves as a crucial intermediate in advanced chemical synthesis, particularly valued for its ability to introduce trifluoroacetyl groups into organic molecules. With the molecular formula C2ClF3O and a molecular weight of 132.47 g/mol, 2,2,2-trifluoroacetyl chloride exhibits the characteristic high reactivity of acid chlorides while benefiting from the unique properties imparted by its three fluorine atoms. The trifluoromethyl group significantly influences the compound's electronic properties, making it an excellent electrophile for nucleophilic substitution reactions. As an ADR Class 2 substance, this compound requires appropriate handling procedures and storage conditions due to its reactive nature. The acid chloride functionality makes it susceptible to hydrolysis in the presence of moisture, generating hydrogen chloride and trifluoroacetic acid. Unlike simpler compounds such as nitrous oxide or bromane, this fluorinated derivative offers enhanced chemical stability and unique reactivity patterns that are particularly valuable in pharmaceutical and agrochemical applications. The compound finds primary industrial applications in pharmaceutical intermediate synthesis, where its trifluoroacetyl group serves as a protecting group or permanent structural element. It is also utilized in the production of specialized fluorinated compounds for agrochemical formulations and in the synthesis of advanced materials requiring fluorine incorporation. The manufacturing of trifluoroacetic acid derivatives represents another significant application area. OYSI maintains reliable supply chains for 2,2,2-trifluoroacetyl chloride to support European chemical manufacturing operations requiring this specialized fluorinated intermediate.

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 a highly reactive organofluorine compound with the molecular formula C2ClF3O and CAS number 354-32-5. This acyl chloride features three fluorine atoms attached to the methyl carbon, making it a trifluorinated derivative of acetyl chloride. With a molecular weight of 132.47 g/mol, it serves as an important building block in fluorine chemistry and pharmaceutical synthesis due to its ability to introduce trifluoroacetyl groups into organic molecules.

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

2,2,2-trifluoroacetyl chloride is a colorless liquid at room temperature with a pungent, acrid odor characteristic of acyl chlorides. It has a boiling point of approximately 27-28°C and a density of about 1.48 g/cm³. The compound is highly reactive with water, undergoing rapid hydrolysis to form trifluoroacetic acid and hydrogen chloride. It is soluble in organic solvents but decomposes in the presence of moisture, making it essential to handle under anhydrous conditions.

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 protecting groups in amino acids and peptides. It serves as a key intermediate in pharmaceutical manufacturing, particularly in the synthesis of fluorinated drugs and agrochemicals. The compound is also utilized in analytical chemistry for derivatization reactions, helping to improve the volatility and detectability of compounds in gas chromatography and mass spectrometry applications.

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

2,2,2-trifluoroacetyl chloride must be handled in a well-ventilated fume hood using appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and lab coat. Work should be conducted under anhydrous conditions to prevent violent hydrolysis reactions. Avoid contact with skin, eyes, and inhalation of vapors. Use proper handling techniques for corrosive materials and ensure emergency shower and eyewash stations are accessible. Always work with small quantities and have appropriate neutralizing agents available.

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

2,2,2-trifluoroacetyl chloride should be stored in tightly sealed containers under anhydrous conditions in a cool, dry, well-ventilated area away from moisture and heat sources. Keep containers in secondary containment to prevent spills and store away from incompatible materials such as water, alcohols, amines, and strong bases. Use amber glass bottles or other suitable chemical-resistant containers. Maintain storage temperature below 25°C and ensure proper labeling with hazard information and expiration dates.

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

In case of skin contact with 2,2,2-trifluoroacetyl chloride, immediately remove contaminated clothing and flush the affected area with copious amounts of water for at least 15 minutes. For eye contact, rinse thoroughly with water and seek immediate medical attention. If inhaled, move the person to fresh air and provide respiratory support if needed. In case of ingestion, do not induce vomiting and seek immediate medical care. Always consult a physician after any exposure incident.

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

2,2,2-trifluoroacetyl chloride must be disposed of as hazardous chemical waste according to local and national regulations. Small quantities can be carefully hydrolyzed under controlled conditions in a fume hood, neutralized, and then disposed of through authorized waste management companies. Never dispose of this compound down drains or in regular waste. Contact certified hazardous waste disposal services and ensure proper documentation. Follow your institution's chemical waste management protocols and maintain disposal records.

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

2,2,2-trifluoroacetyl chloride is classified under ADR Class 2 for transport purposes, indicating it falls under gases or gas-related materials regulations. Transportation must comply with dangerous goods regulations using appropriate packaging, labeling, and documentation. Use UN-specification packaging suitable for corrosive liquids and ensure proper hazard placarding. Transport should be conducted by certified carriers familiar with chemical transport regulations. Maintain proper shipping papers and emergency response information during transit.

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

2,2,2-trifluoroacetyl chloride is subject to REACH regulation in Europe and must be registered for commercial use above specified tonnage thresholds. It is not currently listed as an SVHC (Substance of Very High Concern) but users must comply with CLP regulation for classification, labeling, and packaging. Industrial users should conduct chemical safety assessments and implement appropriate risk management measures. Export/import may require additional permits depending on destination countries and quantities involved.

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 intermediates. As an established chemical supplier, OYSI provides high-quality 2,2,2-trifluoroacetyl chloride with proper documentation, safety data sheets, and regulatory compliance support. Contact OYSI directly for pricing, availability, packaging options, and delivery throughout Europe. We ensure proper handling, packaging, and transport of this reactive compound while maintaining the highest quality and safety standards for our customers.

Data Sources

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