41359-09-5

Basic information

• Product Name: Iminostilbene 10,11-Epoxide-N-carbonyl Chloride
• Synonyms: 1a,10b-Dihydro-;Iminostilbene 10,11-Epoxide-N-carbonyl Chloride
• CAS NO: 41359-09-5
• Molecular Formula: C₁₅H₁₀ClNO₂
• Molecular Weight: 271.6984
• Product Categories: Aromatics, Heterocycles, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals;Aromatics;Heterocycles;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 41359-09-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: Acetone, Chloroform, Dichloromethane, Methanol
• CAS DataBase Reference: Iminostilbene 10,11-Epoxide-N-carbonyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Iminostilbene 10,11-Epoxide-N-carbonyl Chloride(41359-09-5)
• EPA Substance Registry System: Iminostilbene 10,11-Epoxide-N-carbonyl Chloride(41359-09-5)

Safety Data

• Hazardous Substances Data: 41359-09-5(Hazardous Substances Data)

Usage

Description

Iminostilbene 10,11-Epoxide-N-carbonyl Chloride is an organic compound that serves as an intermediate in the synthesis of various pharmaceutical compounds. It is a white solid with specific chemical properties that make it suitable for use in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Iminostilbene 10,11-Epoxide-N-carbonyl Chloride is used as an intermediate for the production of Carbamazepine metabolites. It plays a crucial role in the synthesis process, contributing to the development of medications that can be used for treating various medical conditions.
As an intermediate, Iminostilbene 10,11-Epoxide-N-carbonyl Chloride is essential in the chemical reactions that lead to the formation of the final pharmaceutical product. Its specific properties allow for the creation of Carbamazepine metabolites, which are vital components in the treatment of certain health issues.

Upstream product

• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 256-96-2 dibenzoazepine 

Downstream Products

• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 40421-03-2 trans-10,11-dibromo-10,11-dihydro-5H-dibenzazepine-5-carbonyl chloride 
• 106680-78-8 trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide 

Relevant articles and documents

The Metabolism of Carbamazepine in Humans: Steric Course of the Enzymatic Hydrolysis of the 10,11-Epoxide

Carbamazepine 10,11-oxide (1a,10b-dihydro-6H-dibenzooxirenoazepine-6-carboxamide), a key intermediate in carbamazepine metabolism, was found to be unusually resistant to enzymatic hydrolysis when incubated with microsomal and cytosolic fractions from rabbit, rat, and guinea pig livers.However, its hydrolysis product, trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzoazepine-5-carboxamide, was excreted, as previously reported, both in the free and in conjugated forms, as the main metabolite in the urine of humans under carbamazepine treatment.The free diol and that obtained after treatment with β-glucuronidase/arylsulfatase were both found by Mosher's method to be formed in an enantiomeric excess of 80percent, the prevalent enantiomer having the (-)-10S,11S absolute configuration, as determined by applying the CD exciton coupling method to its bis ester.This finding confirms the pronounced enantioselectivity of the microsomal epoxide hydrolase toward meso and racemic substrates, but is in contrast with the prevalent formation of (R,R)-diols in most other known cases of enzymatic hydrolysis of epoxides.Preparatively useful syntheses of the racemic trans-10,11-dihydro-10,11-diol and of 9-(hydroxymethyl)-10-carbamoylacridan, another carbamazepine metabolite, are reported for the first time.