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(+)-Cinchonine
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-Cinchonine "Pin It")
Description
(+)-Cinchonine
Other Names: Cinchonine, (R)-Cinchonine, Cinchoninum
CAS Number: 118-10-5
Sum Formula: C₁₉H₂₂N₂O
Molar Mass: 294.39 g/mol
Appearance: White to off-white crystalline powder
(+)-Cinchonine is a naturally occurring cinchona alkaloid extracted from the bark of Cinchona species. It is a stereoisomer of cinchonidine and features a rigid bicyclic quinoline structure. Cinchonine is primarily used as a chiral base or organocatalyst in asymmetric synthesis and stereoselective reactions in organic and industrial chemistry.
Chemical and Physical Properties
Melting Point: 255–259°C
Boiling Point: Decomposes before boiling
Solubility in Water: Slightly soluble
Solubility in Organic Solvents: Soluble in ethanol, methanol, chloroform, and dilute acids
Optical Rotation: [α]ᴅ²⁰ +140° (c = 1, ethanol)
Odor: Odorless
Stability: Stable under normal storage conditions
Applications
Used as a chiral ligand or base in asymmetric synthesis
Serves as an organocatalyst in enantioselective transformations
Intermediate or resolving agent in stereochemical separations
Utilized in academic and industrial research for alkaloid-based methodology development
Safety
Signal Word: Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H317 (29.2%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H332 (63.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P261, P264, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, and P501
First Aid Measures
Eye Contact: Rinse thoroughly with water. Seek medical attention if irritation persists
Skin Contact: Wash with soap and water. Remove contaminated clothing
Inhalation: Move to fresh air. Seek medical attention if symptoms occur
Ingestion: Rinse mouth with water. Seek medical advice if feeling unwell
Handling and Storage
Store in a tightly sealed container in a dry, cool, and well-ventilated place
Avoid dust formation and use appropriate personal protective equipment