L-α-Acetoxypropionyl chloride, CAS No. 36394-75-9

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36394-75-9

Catalog No. EBD11032

CAS 36394-75-9

Name L-α-Acetoxypropionyl chloride

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Basic Information

Synonyms: L-±-Acetoxypropionylchloride (S)-(− )-2-Acetoxypropionylchloride (1R)-2-chloro-2-oxo-1-phenylethylacetate (1S)-2-chloro-1-methyl-2-oxoethylacetate (S)-2-Acetoxypropionylchloride L-α-Acetoxypropionylchloride

Molecular Formula: C5H7ClO3

Molecular Weight: 150.56

MDL Number: MFCD00145252

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters

Product Description:

(S)-(-)-2-Acetoxypropionyl chloride is a chiral acyl chloride derivative. It is a colorless to pale yellow liquid that is highly reactive and moisture-sensitive, typically requiring storage under inert conditions. Its key structural features include an acetyl-protected secondary alcohol and a reactive acid chloride group, both attached to a chiral carbon center with (S)-configuration. This compound is primarily employed as a key chiral building block in the synthesis of enantiomerically pure pharmaceuticals. Its main application is as an acylating agent for introducing the (S)-2-acetoxypropionyl moiety, which is a crucial structural motif in the production of certain active pharmaceutical ingredients (APIs). A prominent example is its use in the synthesis of the anticoagulant drug Clopidogrel (Plavix), where it serves as a critical intermediate for constructing the molecule's chiral center. Due to its high reactivity, handling requires strict precautions. It is corrosive and reacts violently with water, alcohols, and amines, releasing hydrogen chloride gas. Its use is almost exclusively confined to controlled industrial and research laboratory settings for targeted synthetic applications, rather than as a general-purpose reagent.

Physical Properties

Boiling Point: 50 °C/5 mmHg(lit.)

Flash Point: 113 °C

Density: 1.189 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.423(lit.)

Storage: 2-8°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 3265