5216-32-0

Basic information

• Product Name: (Z)-α,β-Dichlorostilbene
• Synonyms: (Z)-1,2-Dichloro-1,2-diphenylethene;(Z)-α,β-Dichlorostilbene;trans-Tolan dichloride
• CAS NO: 5216-32-0
• Molecular Formula: C₁₄H₁₀Cl₂
• Molecular Weight: 287.74086
• Mol File: 5216-32-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 67.5°C
• Boiling Point: 323.89°C (rough estimate)
• Flash Point: 174.1°C
• Appearance: /
• Density: 1.1361 (rough estimate)
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Refractive Index: 1.5610 (estimate)
• CAS DataBase Reference: (Z)-α,β-Dichlorostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-α,β-Dichlorostilbene(5216-32-0)
• EPA Substance Registry System: (Z)-α,β-Dichlorostilbene(5216-32-0)

Safety Data

• Hazardous Substances Data: 5216-32-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H14ClNO2/c1-2-15(19)13-10-12(17)8-9-14(13)18-16(20)11-6-4-3-5-7-11/h3-10H,2H2,1H3,(H,18,20)

Upstream product

• 98-07-7 Benzotrichlorid 
• 98-87-3 benzylidene dichloride 
• 2039-86-3 3-bromostyrene 
• 13700-81-7 1,1,2,2-tetrachloro-1,2-diphenylethane 
• 72791-55-0 trichloro[Te(Z)-2-chloro-1,2-diphenylvinyl]tellurium(IV) 
• 67-64-1 acetone 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 501-65-5 diphenyl acetylene 
• 114581-83-8 {tris{(2-pyridyl)methyl}amine(CH₃CN)Cu(I)}{PF₆} 
• 4541-89-3 2-chloro-1,1-diphenylethene 
• 71-43-2 benzene 
• 79-37-8 oxalyl dichloride 
• 3469-17-8 2-diazo-1,2-diphenylethan-1-one 
• 64-19-7 acetic acid 

Downstream Products

• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 501-65-5 diphenyl acetylene 

Relevant articles and documents

Electrolysis of trichloromethylated organic compounds under aerobic conditions catalyzed by the B12 model complex for ester and amide formation

The electrolysis of benzotrichloride at -0.9 V vs. Ag/AgCl in the presence of the B12 model complex, heptamethyl cobyrinate perchlorate, in ethanol under aerobic conditions using an undivided cell equipped with a platinum mesh cathode and a zinc plate anode produced ethylbenzoate in 56% yield with 92% selectivity. The corresponding esters were obtained when the electrolysis was carried out in various alcohols such as methanol, n-propanol, and i-propanol. Benzoyl chloride was detected by GC-MS during the electrolysis as an intermediate for the ester formation. When the electrolysis was carried out under anaerobic conditions, partially dechlorinated products, 1,1,2,2-tetrachloro-1,2-diphenylethane and 1,2-dichlorostilibenes (E and Z forms), were obtained instead of an ester. ESR spin-trapping experiments using 5,5,-dimethylpyrroline N-oxide (DMPO) revealed that the corresponding oxygen-centered radical and carbon-centered radical were steadily generated during the electrolyses under aerobic and anaerobic conditions, respectively. Applications of the aerobic electrolysis to various organic halides, such as substituted benzotrichlorides, are described. Furthermore, the formation of amides with moderate yields by the aerobic electrolysis of benzotrichloride catalyzed by the B12 model complex in the presence of amines in acetonitrile is reported.

Chromium-carbyne complexes: Intermediates for organic synthesis

(Chemical Equation Presented) On the same route: Chromium-carbyne complexes are readily prepared by treatment of 1,1,1-trichloromethyl reagents with chromium(II) chloride. They serve as intermediates in the selective formation of a wide variety of products, such as alkynes, alkenes, β-hydroxy ketones, aldehydes, allylic alcohols, and allenes (see scheme, E = electrophile).

Inter- and innermolecular reactions of chloro(phenyl)carbene

Supramolecular photolyses of 3-chloro-3-phenyl-3H-diazirine (8) were performed within cyclodextrin (CyD) hosts to determine whether these toroidal inclusion compounds could alter the reactivity of the ensuing carbene reaction intermediate, chloro(phenyl)carbene (9). Remarkably, no intramolecular products stemming from carbene 9 could be detected. Instead, modified CyDs were formed via so-called innermolecular reactions. Hence, diazirine 8 was photolyzed in various conventional solvents to gauge the intermolecular reactivity of carbene 9. Relevant results were used to rationalize the CyD innermolecular reaction products.