But-2-enoyl chloride

C4H5ClO

but-2-enoyl chloride

CAS10487-71-5

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Identification

CAS Number
10487-71-5
EC Number
234-010-3
UN Number
2920
PubChem CID
79080

Physical-chemical properties

Molecular Formula
C4H5ClO
Molar Mass
104.53 g/mol
IUPAC Name
but-2-enoyl chloride

Chemical Identifiers

InChI
InChI=1S/C4H5ClO/c1-2-3-4(5)6/h2-3H,1H3
InChI Key
RJUIDDKTATZJFE-UHFFFAOYSA-N

Overview

But-2-enoyl chloride (CAS 10487-71-5) is an α,β-unsaturated acyl chloride featuring both electrophilic carbonyl and vinyl functionalities in its molecular structure. This versatile organic intermediate belongs to the family of acyl chlorides, characterized by the highly reactive -COCl functional group combined with an alkene moiety. With the molecular formula C4H5ClO and a molecular weight of 104.53 g/mol, but-2-enoyl chloride represents a valuable building block in organic synthesis due to its dual reactive sites. The compound's structure incorporates a four-carbon chain with a double bond between the second and third carbons, terminated by the acyl chloride group, making it particularly useful for creating complex molecular architectures. Like other acyl chlorides in this chemical family, including 4-methoxybenzoyl chloride, but-2-enoyl chloride exhibits high reactivity toward nucleophiles, readily undergoing acylation reactions with alcohols, amines, and other nucleophilic species. The additional unsaturation in the carbon chain provides opportunities for further functionalization through addition reactions, cycloadditions, and polymerization processes. This dual reactivity makes it distinctly different from simpler acyl chlorides and enhances its utility in synthetic applications. The compound finds primary applications in pharmaceutical intermediate synthesis, where its unique structure allows for the construction of biologically active compounds containing both amide linkages and alkene functionalities. It serves as a key reagent in the production of specialty polymers and advanced materials, particularly in creating cross-linked systems where the vinyl group can participate in polymerization reactions. Additionally, but-2-enoyl chloride is employed in agrochemical synthesis for developing crop protection agents with enhanced efficacy profiles. OYSI maintains reliable supply chains for but-2-enoyl chloride to support diverse industrial applications across European markets.

Safety & Classification

No Hazard Classification

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

Transport (ADR)

UN Number2920
ADR Class8
Packing GroupII
Tunnel CodeD/E
Proper Shipping NameCrotonoylchlorid
Marine PollutantNo

Frequently Asked Questions

What is but-2-enoyl chloride?

But-2-enoyl chloride is an organic chemical compound with the molecular formula C4H5ClO and CAS number 10487-71-5. This acyl chloride features an unsaturated four-carbon chain with a double bond between the second and third carbons, terminated by a highly reactive chlorocarbonyl functional group. With a molecular weight of 104.53 g/mol, it belongs to the family of α,β-unsaturated acyl chlorides, making it a valuable intermediate in organic synthesis.

What are the physicochemical properties of but-2-enoyl chloride?

But-2-enoyl chloride is typically a colorless to pale yellow liquid at room temperature with a pungent, acrid odor characteristic of acyl chlorides. The compound is highly reactive due to its acyl chloride functionality and readily hydrolyzes in the presence of moisture, releasing hydrogen chloride gas. It has limited solubility in water due to rapid hydrolysis but is soluble in organic solvents such as dichloromethane, chloroform, and aromatic hydrocarbons.

What is but-2-enoyl chloride used for?

But-2-enoyl chloride serves primarily as a synthetic intermediate in pharmaceutical and fine chemical manufacturing. It is used for the preparation of amides, esters, and other derivatives through nucleophilic acyl substitution reactions. The compound finds applications in the synthesis of bioactive molecules, agrochemicals, and specialty chemicals. Its α,β-unsaturated structure makes it particularly valuable for creating compounds with specific stereochemical requirements in medicinal chemistry and materials science.

How to handle but-2-enoyl chloride safely?

But-2-enoyl chloride requires careful handling with appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and lab coats. Work should be conducted in a well-ventilated area or under a fume hood to avoid inhalation of vapors or hydrogen chloride gas released upon hydrolysis. Avoid contact with skin, eyes, and clothing. Use proper grounding techniques when transferring the material to prevent static discharge, and ensure all personnel are trained in emergency procedures.

How to store but-2-enoyl chloride correctly?

But-2-enoyl chloride should be stored in tightly sealed containers made of compatible materials, away from moisture and humidity. Keep the compound in a cool, dry, well-ventilated area away from heat sources and incompatible substances such as alcohols, amines, and water. Storage areas should be equipped with appropriate spill containment measures and maintained at stable temperatures. Regular inspection of container integrity is essential due to the corrosive nature of the compound.

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

But-2-enoyl chloride contact requires immediate action. For skin contact, remove contaminated clothing and wash the affected area thoroughly with soap and water for at least 15 minutes. In case of eye contact, flush immediately with clean water for at least 15 minutes and seek medical attention. If inhaled, move the person to fresh air and monitor breathing. For ingestion, do not induce vomiting and seek immediate medical attention. Always consult safety data sheets for specific guidance.

How to dispose of but-2-enoyl chloride appropriately?

But-2-enoyl chloride disposal must comply with local and national hazardous waste regulations. The compound should be collected in appropriate containers and disposed of through licensed hazardous waste disposal facilities. Small quantities may be carefully hydrolyzed under controlled conditions to form the corresponding carboxylic acid, but this should only be performed by trained personnel with proper safety equipment. Never dispose of the compound down drains or in regular waste streams due to its reactive and potentially harmful nature.

How to transport but-2-enoyl chloride?

But-2-enoyl chloride is classified under ADR Class 8 (Corrosive substances) with Packing Group II, indicating moderate danger level. Transportation requires appropriate UN-approved packaging designed for corrosive liquids, proper labeling with Class 8 hazard labels, and accompanying transport documentation. Vehicles must be equipped with appropriate emergency equipment and drivers should be trained in ADR requirements. Shipments must comply with quantity limitations and routing restrictions as specified in dangerous goods regulations.

Is but-2-enoyl chloride subject to specific regulations?

But-2-enoyl chloride is subject to various chemical regulations including REACH registration requirements for manufacture or import in the European Union above certain tonnage thresholds. The compound is not currently listed as a Substance of Very High Concern (SVHC). However, it must comply with CLP regulation for classification, labeling, and packaging. Users should maintain safety data sheets, implement appropriate risk management measures, and ensure compliance with local occupational health and safety regulations.

Where to buy but-2-enoyl chloride in Europe?

But-2-enoyl chloride is available through OYSI, a specialized European distributor of technical chemicals serving various industries across the continent. OYSI provides high-quality chemical products with comprehensive technical support and regulatory compliance documentation. As an established chemical distributor, OYSI ensures proper handling, storage, and transportation of reactive compounds like but-2-enoyl chloride. Contact OYSI directly for availability, specifications, and delivery options tailored to your specific requirements and location within Europe.

Data Sources

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