253684-31-0

Basic information

• Product Name: (Z)-1-[1-bromo-2-(4-methoxyphenyl)vinyl]benzene
• Synonyms: (Z)-1-[1-bromo-2-(4-methoxyphenyl)vinyl]benzene
• CAS NO: 253684-31-0
• Molecular Weight: 289.172
• Mol File: 253684-31-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (Z)-1-[1-bromo-2-(4-methoxyphenyl)vinyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-[1-bromo-2-(4-methoxyphenyl)vinyl]benzene(253684-31-0)
• EPA Substance Registry System: (Z)-1-[1-bromo-2-(4-methoxyphenyl)vinyl]benzene(253684-31-0)

Safety Data

• Hazardous Substances Data: 253684-31-0(Hazardous Substances Data)

Upstream product

• 60512-57-4 1-(2,2-dibromovinyl)-4-methoxybenzene 
• 98-80-6 phenylboronic acid 
• 934-56-5 trimethyl(phenyl)stannane 
• 123-11-5 4-methoxy-benzaldehyde 
• 186968-63-8 2-(Bromo-phenyl-methyl)-5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide 

Downstream Products

• 7380-78-1 4-(phenylethynyl)anisole 
• 1694-19-5 E-1-(phenyl)-2-(4'-methoxyphenyl)ethene 

Relevant articles and documents

One-pot conversion of 1,1-dibromoalkenes into internal alkynes by sequential Suzuki-Miyaura and dehydrobromination reactions

A protocol for the one-pot synthesis of internal alkynes from 1,1-dibromoalkenes is reported. The method is hinged upon the Suzuki-Miyaura cross-coupling of 2-aryl- or 2-heteroaryl-1,1-dibromoalkenes with aryl or heteroaryl boronic acids or borate esters

A modified Suzuki reaction of 1,1-dibromo-1-alkenes

The (E)-bromides in 1,1-dibromo-1-alkenes were stereoselectively coupled with aryl- or alkenylboronic acids to give the corresponding (Z)-1- Aryl(alkenyl)-1-bromo-1-alkenes. Tris(2-furyl)phosphine (TFP) was used as the ligand to palladium, and the combination of 1,4-dioxane and aqueous sodium carbonate produced the best results.

An easy access to trisubstituted vinyl chlorides and improved synthesis of chloro/bromostilbenes

The α-chlorophosphonates (OCH2CMe2CH2O)P(O)CHCl-C6H4-4-R [R=H (4), Me (5), OMe (6)], which are now readily accessible, react with ketones R'C(O)R' in the presence of NaH (without recourse to the more expensive t- BuLi) to afford trisubstituted vinyl halides R'C(R')=CCl(C6H4-4-R) in good yields. The corresponding α-bromophosphonates [R=H (7), Me (8)] failed to react with ketones and gave the symmetrical acetylenes 4-R-C6H4-C=C- C6H44-R as isolable products in low yield. We have found that K2CO3 in refluxing xylene is a good base for the synthesis of chlorostilbenes; using this base the bromostilbenes ArCH=CBr(C6H44-R) can be prepared in significantly higher yields than by using NaH. The stereochemistry of two of the trisubstituted vinyl chlorides is unambiguously proven by X-ray structure determination. Thus for (Cl)PhC=CPh(Me), the isomer with the upfield NMR shift for the CH3 protons and for (Cl)PhC=C(Ph)(C6H4-4-Me), the isomer with the downfield NMR shift for the -C6H4-4-CH3 protons have Z stereochemistry.