948-99-2

Basic information

• Product Name: Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis-
• Synonyms: Benzene,1,1'-(1-chloro-1,2-ethenediyl)bis-, (Z)-; Stilbene, a-chloro-, (Z)-(8CI); (Z)-1-Chloro-1,3-diphenylethene; NSC 168887; a-Chloro-cis-stilbene
• CAS NO: 948-99-2
• Molecular Formula: C14H11 Cl
• Molecular Weight: 214.694
• Mol File: 948-99-2.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis-(948-99-2)
• EPA Substance Registry System: Benzene,1,1'-[(1Z)-1-chloro-1,2-ethenediyl]bis-(948-99-2)

Safety Data

• Hazardous Substances Data: 948-99-2(Hazardous Substances Data)

Upstream product

• 15951-99-2 meso-1,2-dichloro-1,2-diphenylethane 
• 698-88-4 (2,2-dichlorovinyl)benzene 
• 38111-44-3 phenylzinc(II) bromide 
• 15951-99-2 1,2-dichloro-1,2-diphenylethane 
• 75-09-2 dichloromethane 
• 947-90-0 2,2-diphenyl-vinylamine 
• 100-34-5 benzene diazonium chloride 
• 536-74-3 phenylacetylene 
• 67-64-1 acetone 
• 98-88-4 benzoyl chloride 
• 13440-24-9 anti-1,2-dibromo-1,2-diphenylethane 
• 14447-41-7 (E)-1-bromo-1,2-diphenylethene 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 108-86-1 bromobenzene 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 948-98-1 (E)-α-chlorostilbene 
• 501-65-5 diphenyl acetylene 
• 588-59-0 stilbene 
• 833-81-8 (E)-1,2-diphenylpropene 
• 447-31-4 Desyl chloride 
• 20488-54-4 trans-1,2-difluoro-1,2-diphenylethylene 
• 20488-55-5 cis-α,α'-difluorostilbene 
• 19191-03-8 (E)-1-methoxy-1,2-diphenylethene 
• 19202-54-1 (Z)-1-methoxy-1,2-diphenylethene 
• 947-72-8 9-chlorophenanthrene 
• 100-52-7 benzaldehyde 
• 78229-57-9 <1'R-(1'α,2'β,3'α,4'α)>-3'-Chlor-3',4'-diphenyldispiro-3,3''-dion 
• 78229-52-4 <1R-(1α,2β,3α,4β)>-Tetraspiro-3',3'',3''',3''''-tetraon 

Relevant articles and documents

Regioselective Synthesis of α-Functional Stilbenes via Precise Control of Rapid cis- trans Isomerization in Flow

The rapid cis-trans isomerization of α-anionic stilbene was regioselectively controlled by using flow microreactors, and its reaction with various electrophiles was conducted. The reaction time was precisely controlled within milliseconds to seconds at -50 °C to selectively give the cis- or trans-isomer in high yields. This synthetic method in flow was well-applied to synthesize precursors of commercial drug compound, (E)- and (Z)-tamoxifen with high regioselectivity and productivity.

Iodine(III)-Mediated Oxidative Hydrolysis of Haloalkenes: Access to α-Halo Ketones by a Release-and-Catch Mechanism

An unprecedented iodine(III)-mediated oxidative transposition of vinyl halides has been accomplished. The products obtained, α-halo ketones, are useful and polyvalent synthetic precursors. There are only a handful of reported examples of the direct conversion of vinyl halides to their corresponding α-halo carbonyl compounds. Insights into the mechanism and demonstration that this synthetic transformation can be done under enantioselective conditions are reported.

Iridium-catalyzed addition of aroyl chlorides and aliphatic acid chlorides to terminal alkynes

Iridium complexes show high catalytic activity in intermolecular additions of acid chlorides to terminal alkynes to afford valuable (Z)-β-chloro- α,β-unsaturated ketones. Ligands in the catalytic system play a crucial role in this reaction. An N-heterocyclic carbene (NHC) is an efficient ligand for the addition of aroyl chlorides, while dicyclohexyl(2-methylphenyl) phosphine (PCy2(o-Tol)) is indispensable for the reaction of aliphatic acid chlorides. The addition reactions proceed regio- and stereoselectively with suppression of decarbonylation and β-hydrogen elimination, which have been two major intrinsic problems in transition-metal-catalyzed reactions. Stoichiometric reactions of active iridium catalysts with aroyl chlorides and aliphatic acid chlorides are carried out to gain insights into the reaction mechanisms.