7619-53-6

Basic information

• Product Name: clomifene citrate
• Synonyms: cis-clomiphene citrate;Zuclomiphene-D5 Citrate
• CAS NO: 7619-53-6
• Molecular Formula: C₆H₈O₇*C₂₆H₂₈ClNO
• Molecular Weight: 598.08314
• Mol File: 7619-53-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: clomifene citrate(CAS DataBase Reference)
• NIST Chemistry Reference: clomifene citrate(7619-53-6)
• EPA Substance Registry System: clomifene citrate(7619-53-6)

Safety Data

• Hazardous Substances Data: 7619-53-6(Hazardous Substances Data)

Usage

Uses

cis-Clomiphene Citrate is the cis isomer of Clomiphene (C587025). Found to be antiestrogenic and a more potent inhibitor of LH secretion than the trans isomer.

Upstream product

• 77-92-9 citric acid 
• 50-41-9 clomifene citrate 
• 35258-26-5 <4-<2-(diethylamino)ethoxy>phenyl>magnesium bromide 
• 501-65-5 diphenyl acetylene 
• 911-45-5 Zuclomiphene 
• 72474-40-9 cis-1-Chloro-2-(4-hydroxyphenyl)-1,2-diphenylethylene 
• 72474-42-1 (Z)-(1-chloro-2-(4-methoxyphenyl)ethene-1,2-diyl)dibenzene 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 352-34-1 4-fluoro-1-iodobenzene 

Relevant articles and documents

Stereoselective Nickel(II)-Catalyzed Addition of Aryl Grignards to Diphenylacetylene in the Synthesis of Zuclomiphene

Stereoselective synthesis of zuclomiphene was developed using nickel-catalyzed addition of 4-fluorophenylmagnesium bromide to 1,2-diphenylacetylene, followed by quenching with a chlorinating reagent. Since the aryl fluoride addition and chlorination reactions occur consecutively in one pot, the cis orientation of the two phenyl groups of 1,2-diphenylacetylene is conserved, leading to the highly selective synthesis of zuclomiphene. The use of the Grignard reagent resulted in the presence of bromide ions in the reaction mixture, which led to the formation of the bromo-analog of zuclomiphene. Alternative routes were then explored to overcome this issue to yield high-purity zuclomiphene.

Processes for the Preparation of Zuclomiphene and Intermediates Thereof

The present invention provides processes for the preparation of zuclomiphene, as well as intermediates useful in the preparation thereof. In particular, processes are provided for the carbometallation of diphenylacetylene with a compound of Formula (3) to afford either zuclomiphene or an intermediate which is converted to zuclomiphene.