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:

97% ^*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

Detection and reactivity of Pd((C₈H₁₄)PCH ₂CH₂P(C₈H₁₄))(CHPhCH ₂Ph)(H) as determined by parahydrogen-enhanced NMR spectroscopy

10.1021/ja044875f

This research aimed to detect and study the reactivity of palladium complexes, specifically Pd(bcope)(OTf)2 (where bcope is (C8H14)PCH2CH2P(C8H14)), using parahydrogen-induced polarization (PHIP) effect in NMR spectroscopy. The study demonstrated that the PHIP effect could be used to detect metal complexes without the need for enhancement of a hydride resonance, and it provided insights into the reactions of the palladium complex with alkynes, particularly the formation and transformation of intermediates and products such as cis- and trans-stilbene. The researchers observed that the PdCHPhCH2Ph group of the complex transforms most readily into trans-stilbene, confirming that hydride insertion is reversible and involves a discrete Pd(bcope)(PhCH=CHPh)(H)2 intermediate. The study concluded that PHIP is not limited to the study of metal dihydrides and can enhance the detection of organic components within a metal's ligand sphere, offering a new approach to map concerted catalytic hydrogenation by a palladium(II) bis-phosphine complex.

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