113619-15-1

Basic information

• Product Name: (Z)-1-iodo-1,2-diphenyl-1-butene
• Synonyms: (Z)-1-iodo-1,2-diphenyl-1-butene
• CAS NO: 113619-15-1
• Molecular Weight: 334.2
• Mol File: 113619-15-1.mol

Chemical Properties

• CAS DataBase Reference: (Z)-1-iodo-1,2-diphenyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-iodo-1,2-diphenyl-1-butene(113619-15-1)
• EPA Substance Registry System: (Z)-1-iodo-1,2-diphenyl-1-butene(113619-15-1)

Safety Data

• Hazardous Substances Data: 113619-15-1(Hazardous Substances Data)

Upstream product

• 622-76-4 1-phenyl-1-butyne 
• 591-51-5 phenyllithium 
• 557-20-0 diethylzinc 
• 811-49-4 ethyllithium 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 10540-29-1 tamoxifen 
• 66584-35-8 tamoxifen hydrochloride 

Relevant articles and documents

Carbolithiation of diphenylacetylene as a stereoselective route to (Z)-tamoxifen and related tetrasubstituted olefins

(Chemical Equation Presented) Carbolithiation of diphenylacetylene can be exploited to generate (E)-1-lithio-1,2-diphenylalkyl-1-enes which can be reacted in situ with triisopropylborate to stereoselectively provide (E)-1,2-diphenyl-1-alkylene boronic acids. These tetrasubstituted vinylboronic acids served as versatile intermediates for the generation of tetrasubstituted olefins with retention of stereochemistry. The application of this method for the stereoselective synthesis of (Z)-tamoxifen and related analogues is described.

A Nickel-catalyzed carbozincation of aryl-substituted alkynes

The addition of dialkylzincs or diphenylzinc to substituted phenylacetylenes in the presence of catalytic amounts of Ni(acac)2 in THF:NMP mixtures produces syn-carbozincation products with good to excellent regio- and stereoselectivity. After quenching with an electrophile (iodine, acyl chloride, allyl bromide) tetrasubstituted olefines are obtained in good to satisfactory yields. An intramolecular version of the reaction is possible using a terminal triple bond bearing an iodine at a remote position. More substituted iodo-alkynes furnish only reductive elimination products. An application to a stereoselective synthesis of (Z)-tamoxifen (Z:E > 99:1) has been developed.

New nickel-catalyzed carbozincation of alkynes: A short synthesis of (Z)-tamoxifen

A new highlight in the repertoire of carbometalation reactions is the highly stereo- and regioselective nickel-catalyzed carbozincation of internal alkynes. This is exemplified by a short and effective synthesis of the anti-breast-cancer drug (Z)-tamoxifen. This reaction also allows the stereoselective synthesis of various tri- and tetrasubstituted olefins in good yield.