2-phenylacetyl chloride

C8H7ClO

CAS103-80-0

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Identification

CAS Number
103-80-0
EC Number
203-146-5
UN Number
2577
PubChem CID
7679

Physical-chemical properties

Molecular Formula
C8H7ClO
Molar Mass
154.59 g/mol
IUPAC Name
2-phenylacetyl chloride

Chemical Identifiers

InChI
InChI=1S/C8H7ClO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2
InChI Key
VMZCDNSFRSVYKQ-UHFFFAOYSA-N

Overview

2-phenylacetyl chloride (CAS 103-80-0) is an aromatic acyl chloride characterized by high reactivity and versatility in organic synthesis applications. This important chemical intermediate belongs to the family of acyl chlorides, featuring a phenyl group attached to an acetyl chloride moiety. With the molecular formula C8H7ClO and a molecular weight of 154.59 g/mol, 2-phenylacetyl chloride serves as a crucial building block in pharmaceutical and fine chemical manufacturing. The compound is classified under ADR Class 8, indicating its corrosive nature, which requires careful handling and appropriate safety measures during storage and transportation. The high reactivity of 2-phenylacetyl chloride stems from the electrophilic carbonyl carbon, making it an excellent acylating agent for various nucleophilic substrates. This reactivity profile is shared with related compounds such as 4-methoxybenzoyl chloride, though the phenylacetic structure provides unique synthetic advantages in specific applications. The compound readily reacts with alcohols, amines, and other nucleophiles to form esters, amides, and other derivatives, making it invaluable in organic synthesis. Primary industrial applications include the synthesis of pharmaceutical intermediates, particularly in the production of anti-inflammatory compounds and other therapeutic agents. The compound also finds extensive use in the manufacture of specialty chemicals and as a key reagent in peptide synthesis, where it serves as a protecting group or coupling agent. Additionally, it plays a role in the production of various aromatic compounds used in agrochemical formulations. Due to its corrosive properties, proper handling protocols must be followed, including the use of appropriate personal protective equipment and storage in moisture-free environments to prevent hydrolysis. OYSI maintains reliable supply chains for 2-phenylacetyl chloride to support European chemical manufacturing operations.

Safety & Classification

No Hazard Classification

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

Transport (ADR)

UN Number2577
ADR Class8
Packing GroupII
Tunnel CodeE
Proper Shipping NamePhenylacetylchlorid
Marine PollutantNo

Frequently Asked Questions

What is 2-phenylacetyl chloride?

2-phenylacetyl chloride is an organic chemical compound with the molecular formula C8H7ClO and CAS number 103-80-0. It belongs to the acyl chloride family, characterized by the presence of a carbonyl group bonded to a chlorine atom. This compound features a phenyl ring attached to an acetyl chloride functional group, making it a valuable intermediate in organic synthesis. With a molecular weight of 154.59 g/mol, it serves as an important building block in pharmaceutical and chemical manufacturing processes.

What are the physicochemical properties of 2-phenylacetyl chloride?

2-phenylacetyl chloride is typically a colorless to pale yellow liquid at room temperature with a pungent, acrid odor characteristic of acyl chlorides. As an acyl chloride, it is highly reactive with water and alcohols, undergoing hydrolysis to form the corresponding carboxylic acid and hydrogen chloride. The compound is generally soluble in organic solvents such as dichloromethane, chloroform, and benzene, but reacts violently with protic solvents like water and alcohols due to its electrophilic nature.

What is 2-phenylacetyl chloride used for?

2-phenylacetyl chloride is primarily used as an acylating agent in organic synthesis and pharmaceutical manufacturing. It serves as a key intermediate in the production of various pharmaceuticals, agrochemicals, and fine chemicals. The compound is commonly employed in Friedel-Crafts acylation reactions to introduce phenylacetyl groups into aromatic compounds. Additionally, it is used in the synthesis of esters, amides, and other derivatives through nucleophilic acyl substitution reactions, making it valuable in research laboratories and industrial chemical processes.

How to handle 2-phenylacetyl chloride safely?

2-phenylacetyl chloride must be handled with extreme caution due to its corrosive and reactive nature. Always wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and protective clothing. Work in a well-ventilated area or under a fume hood to avoid inhalation of vapors. Avoid contact with water, alcohols, and other protic substances as these can cause violent reactions. Use dry, inert atmosphere conditions when possible and ensure all equipment is thoroughly dried before use to prevent unwanted hydrolysis reactions.

How to store 2-phenylacetyl chloride correctly?

2-phenylacetyl chloride should be stored in tightly sealed, dry containers made of compatible materials such as glass or PTFE-lined vessels. Keep the compound in a cool, dry place away from moisture, heat sources, and incompatible materials including water, alcohols, amines, and strong bases. Store under an inert atmosphere such as nitrogen or argon to prevent hydrolysis. Ensure storage areas are well-ventilated and equipped with appropriate spill containment measures. Regular inspection of container integrity is essential due to the compound's corrosive nature.

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

In case of skin contact with 2-phenylacetyl chloride, immediately remove contaminated clothing and flush the affected area with copious amounts of water for at least 15 minutes. For eye contact, rinse immediately with water for at least 15 minutes and seek medical attention promptly. If inhaled, move the person to fresh air immediately and seek medical attention if breathing difficulties occur. In case of ingestion, do not induce vomiting and seek immediate medical attention. Always consult a poison control center or medical professional for specific guidance.

How to dispose of 2-phenylacetyl chloride properly?

2-phenylacetyl chloride must be disposed of in accordance with local, national, and international hazardous waste regulations. The compound should never be poured down drains or released into the environment due to its reactive and potentially harmful nature. Small quantities can be carefully hydrolyzed under controlled conditions to form less hazardous products, but this should only be done by trained personnel. Contact licensed hazardous waste disposal companies for proper collection and treatment. Always consult local environmental authorities for specific disposal requirements and approved facilities.

How to transport 2-phenylacetyl chloride?

2-phenylacetyl chloride is classified as ADR Class 8 (Corrosive substances), Packing Group II, indicating it poses moderate danger during transport. The compound must be packaged in UN-approved containers suitable for corrosive liquids and properly labeled with appropriate hazard markings. Transport vehicles must comply with ADR regulations for Class 8 substances, including proper ventilation and emergency equipment. Drivers must possess valid ADR training certificates. Ensure proper documentation including transport documents and emergency response information accompanies all shipments to comply with international transport regulations.

Is 2-phenylacetyl chloride subject to specific regulations?

2-phenylacetyl chloride is subject to various chemical regulations including REACH (Registration, Evaluation, Authorization and restriction of Chemicals) in the European Union, requiring proper registration for commercial use. The compound is not currently listed as a Substance of Very High Concern (SVHC) under REACH. However, as a corrosive substance, it must comply with CLP (Classification, Labelling and Packaging) regulations for proper hazard communication. Users must also adhere to occupational safety regulations and may need permits for industrial use depending on local jurisdictions.

Where to buy 2-phenylacetyl chloride in Europe?

2-phenylacetyl chloride is available through OYSI, a trusted European distributor of specialty chemicals serving industrial and research customers across the continent. OYSI provides high-quality chemical products with proper documentation and regulatory compliance for European markets. As a specialized chemical requiring careful handling and storage, it's essential to purchase from reputable suppliers who understand the technical requirements and safety protocols. Contact OYSI directly for availability, specifications, and delivery options tailored to your specific needs and location within Europe.

Data Sources

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