(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride, CAS No. 39637-74-6

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39637-74-6

Catalog No. EBD967026

CAS 39637-74-6

Name (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride

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Basic Information

Synonyms: (-)-(1S,4R)-CamphanoylChloride (-)-Camphanicacidchloride (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonylchloride 4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonylchloride (1S)-(-)-CamphanicAcidChloride (1S)-(-)-camphanicchloride

Molecular Formula: C10H13ClO3

Molecular Weight: 216.66

MDL Number: MFCD00135626

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

Product Description:

(-)-(1S,4R)-Camphanic chloride is a chiral bicyclic acid chloride derived from camphor. It is a white to off-white crystalline solid that is widely recognized as a versatile chiral derivatizing agent and resolving auxiliary in organic synthesis. Its primary application is in the pharmaceutical and fine chemical industries for the resolution of racemic mixtures of alcohols, amines, and other chiral compounds. The reaction with (-)-(1S,4R)-camphanic chloride forms diastereomeric derivatives (esters or amides) that can be separated by conventional techniques like crystallization or chromatography. After separation, the pure enantiomer can be recovered by cleaving the camphanate group. This makes it a crucial chiral intermediate and building block for producing enantiomerically pure active pharmaceutical ingredients (APIs) and other high-value chiral molecules. The compound is moisture-sensitive and should be stored under inert conditions. It is a key reagent in asymmetric synthesis and analytical chemistry for determining enantiomeric purity.

Physical Properties

Melting Point: 67-70 °C

Boiling Point: 299.5 °C at 760 mmHg

Flash Point: 125 °C

Density: 1.298 g/cm3

Solubility: decomposes

Storage: −20°C

Safety Information

Packing Level: II

Hazard Category: 8

Transport Codes: 3261