cis-Stilbene

Base Information

• Chemical Name: cis-Stilbene
• CAS No.: 645-49-8
• Molecular Formula: C14H12
• Molecular Weight: 180.249
• Hs Code.: 2902909090
• European Community (EC) Number: 211-445-7
• NSC Number: 126882,66424
• UNII: TTG5048Y3K
• DSSTox Substance ID: DTXSID5026049
• Nikkaji Number: J7.069F
• Wikipedia: (Z)-Stilbene
• Wikidata: Q3244815
• Metabolomics Workbench ID: 55253
• ChEMBL ID: CHEMBL393702
• Mol file: 645-49-8.mol

Synonyms:cis-Stilbene;(Z)-Stilbene;645-49-8;(Z)-1,2-Diphenylethene;cis-1,2-Diphenylethylene;Isostilbene;Stilbene, (Z)-;cis-Diphenylethene;[(Z)-2-Phenylethenyl]benzene;Z-stilbene;(Z)-1,2-Diphenylethylene;Benzene, 1,1'-(1,2-ethenediyl)bis-, (Z)-;CCRIS 5932;HSDB 4270;1,cis-2-Diphenylethene;cis-1,2-Diphenylethene;EINECS 211-445-7;1,cis-2-Diphenylethylene;NSC 66424;1,1'-(Z)-ethene-1,2-diyldibenzene;UNII-TTG5048Y3K;TTG5048Y3K;Benzene, 1,1'-(1Z)-1,2-ethenediylbis-;DTXSID5026049;CHEBI:36008;NSC-66424;(Z)-(1,2-ethenediyl)-1,1-bisbenzene;(Z)-1,1'-(1,2-ethenediyl)bisbenzene;1,1'-[(1Z)-ethene-1,2-diyl]dibenzene;[Z]-1,2-diphenylethene;Dibenzal (cis);Stilbene, cis-;MFCD00004788;cis-Stilbene, 96%;STILBENE CIS-FORM;MLS001050167;1,2-Diphenylethene, (Z)-;CHEMBL393702;DTXCID406049;STILBENE CIS-FORM [MI];[(1Z)-2-phenylethenyl]benzene;[(Z)-2-Phenylethenyl]benzene #;NSC66424;Tox21_200350;NSC126882;AKOS016010738;CS-W016007;LS-1551;NSC-126882;CIS-1,2-DIPHENYLETHYLENE [HSDB];NCGC00091103-01;NCGC00091103-02;NCGC00257904-01;AS-57837;CAS-645-49-8;SMR001216580;1,1'-(1,2-Ethanediyl)bis[benzene], cis;Benzene,1'-(1,2-ethenediyl)bis-, (Z)-;S0089;(1,2-Ethenediyl)-1,1'-bisbenzene, (Z)-;Benzene, 1,1'-(1,2-ethenedyl)bis-, (Z)-;A800711;A834808;A867862;Q3244815

Chemical Property of cis-Stilbene

Chemical Property:

• Appearance/Colour: Pale yellow liquid
• Melting Point: -5°C
• Refractive Index: n20/D 1.622(lit.)
• Boiling Point: 307 °C at 760 mmHg
• Flash Point: 128.5 °C
• PSA: 0.00000
• Density: 1.044 g/cm³
• LogP: 3.85700
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 180.093900383
• Heavy Atom Count: 14
• Complexity: 149

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C(C=C1)C=CC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\C2=CC=CC=C2

Technology Process of cis-Stilbene

There total 771 articles about cis-Stilbene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

benzylidene dichloride (98-87-3) → cis-stilben (645-49-8) + (E)-1,2-diphenyl-ethene (103-30-0) + benzaldehyde (100-52-7) + toluene (108-88-3,15644-74-3,16713-13-6)

Guidance literature:

With sodium formate; sodium carbonate; palladium on activated charcoal; In N,N-dimethyl acetamide; at 120 ℃; for 7.5h;

DOI:10.1080/00397910500214458

Reference yield: 53.0%

(E)-1,2-diphenyl-ethene (103-30-0) → 2,3-diphenyloxirane (1689-71-0,17619-97-5,25144-18-7,38628-70-5,40102-60-1,1439-07-2) + cis-stilben (645-49-8) + benzaldehyde (100-52-7) + benzil (134-81-6)

Guidance literature:

With 9,10-Dicyanoanthracene; oxygen; In acetonitrile; Title compound not separated from byproducts; Irradiation;

DOI:10.1021/ja00521a074

Reference yield: 35.0%

(E)-1,2-diphenyl-ethene (103-30-0) → cis-stilben (645-49-8) + benzaldehyde (100-52-7) + Desyl chloride (447-31-4)

Guidance literature:

With oxygen; iron(III) chloride; In pyridine; for 0.5h; Irradiation;

DOI:10.1021/jo00316a007

upstream raw materials:

styrene

benzenediazonium

(E)-1,2-diphenyl-ethene

hexane

Downstream raw materials:

2r,3c-diphenyl-cyclopropane-carboxylic acid-(1ξ)-ethyl ester

erythro-1-bromo-2-methoxy-1,2-diphenylethane

1,2-diphenyl-1,2-ethanediol

DL-1,2-diphenylethane-1,2-diol

Refernces

• 1、 Hara, Kenji,Kanamori, Yoshikazu,Sawamura, Masaya. "Ring carbon functionalization of N-heterocyclic carbene ligand with ester groups. Electronic effect of ester groups on coordination properties". . p. 1781 - 1786. Retrieved 2006.
• 2、 Schroeder, J?rg. "Picosecond kinetics of trans-cis-photoisomerisations: from jet-cooled molecules to compressed solutions". . p. 643 - 650. Retrieved 1997.
• 3、 Prestwich, Tom G.,Blazina, Damir,Duckett, Simon B.,Dyson, Paul J.. "A parahydrogen study of catalytic hydrogenation by diphosphane-substituted triruthenium clusters". . p. 4381 - 4387. Retrieved 2004.
• 4、 Nakano, Ryo,Sugita, Kengo,Yamashita, Makoto. "Cycloaddition of Dialkylalumanyl Anion toward Unsaturated Hydrocarbons in (1+2) and (1+4) Modes". . . Retrieved 2019.
• 5、 Lewis,Magel,Lipkin. "-". . p. 2973,2976. Retrieved 1940.
• 6、 Eberhard, Michael R.. "Insights into the heck reaction with PCP pincer palladium(II) complexes". . p. 2125 - 2128. Retrieved 2004.
• 7、 Kendall, John T.. "A high yielding synthesis of [5-14C]-5H-dibenzo[a,d]cyclohepten-5-one (dibenzosuberenone) using [14C]-dimethylformamide". . p. 477 - 484. Retrieved 1999.
• 8、 Gonzalez-Arellano,Corma,Iglesias,Sanchez. "Pd(II)-Schiff base complexes heterogenised on MCM-41 and delaminated zeolites as efficient and recyclable catalysts for the heck reaction". . p. 1758 - 1764. Retrieved 2004.
• 9、 Baldovi, Maria V.,Corma, Avelino,Garcia, Hermenegildo,Marti, Vicente. "Shape-Selective Photosensitized Isomerization of Stilbene Using a Benzophenone Incorporated Within Acid Zeolites". . p. 9447 - 9450. Retrieved 1994.
• 10、 Schoenfelder, Daniel,Fischer, Karl,Schmidt, Manfred,Nuyken, Oskar,Weberskirch, Ralf. "Poly(2-oxazoline)s functionalized with palladium carbene complexes: Soluble, amphiphilic polymer supports for C-C coupling reactions in water". . p. 254 - 262. Retrieved 2005.