CIS-STILBENE OXIDE

Base Information

• Chemical Name: CIS-STILBENE OXIDE
• CAS No.: 1689-71-0
• Molecular Formula: C14H12 O
• Molecular Weight: 196.249
• Hs Code.: 2910900090
• European Community (EC) Number: 215-877-7
• UNII: GIX80CN6Z7
• Nikkaji Number: J878H
• Wikidata: Q27121646
• Metabolomics Workbench ID: 27971
• Mol file: 1689-71-0.mol

Synonyms:Bibenzyl, a,a'-epoxy-, cis- (8CI); Oxirane, 2,3-diphenyl-, cis-;NSC 133513; Stilbene cis-epoxide; cis-1,2-Diphenylethylene oxide;cis-2,3-Diphenyloxirane; cis-Stilbene oxide

Chemical Property of CIS-STILBENE OXIDE

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 38-40 °C(lit.)
• Boiling Point: 126-132 °C(Press: 4 Torr)
• Flash Point: 109 C (closed cup)
• PSA: 12.53000
• Density: 1.136±0.06 g/cm3(Predicted)
• LogP: 3.49920
• Storage Temp.: 2-8°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 196.088815002
• Heavy Atom Count: 15
• Complexity: 179

Purity/Quality:

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

cis-Stilbene oxide 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Other Aromatic Compounds
• Canonical SMILES: C1=CC=C(C=C1)C2C(O2)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]2[C@H](O2)C3=CC=CC=C3

Technology Process of CIS-STILBENE OXIDE

There total 313 articles about CIS-STILBENE OXIDE 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: 79.0%

(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) + benzaldehyde (100-52-7)

Guidance literature:

With C₂₀H₂₄CoN₂O₆⁽¹⁺⁾*NO₃^(1-)*H₂O; oxygen; isobutyraldehyde; In acetonitrile; at 60 ℃; for 8h; under 760.051 Torr; Time;

DOI:10.1016/j.poly.2013.03.050

Reference yield: 74.0%

cis-stilben (645-49-8) → benzaldehyde (100-52-7) + cis-1,2-diphenyloxirane (1689-71-0) + trans-Stilbene oxide (1439-07-2)

Guidance literature:

With meso-tetrakis(pentafluorophenyl)porphirinato Fe(IV) nitrate; dihydrogen peroxide; In dichloromethane; acetonitrile; at 20 ℃; for 0.166667h; Further Variations:; Reagents; Product distribution;

DOI:10.1002/1521-3773(20001016)39:20<3646::AID-ANIE3646>3.0.CO;2-Q

Reference yield: 64.5%

(E)-1,2-diphenyl-ethene (103-30-0) → benzaldehyde (100-52-7) + cis-1,2-diphenyloxirane (1689-71-0) + trans-Stilbene oxide (1439-07-2)

Guidance literature:

With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N₃)₂; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1002/chem.201604498

upstream raw materials:

peracetic acid

cis-stilben

Perbenzoic acid

(SR,SR)-2-chloro-1,2-diphenyl-1-ethanol

Downstream raw materials:

(R*,R*)-1,2-diphenyl-2-pyrrolidin-1-yl-ethanol

cis-1,2-epoxy-1,2-diphenyl-1-(trimethylsilyl)ethane

cis-2-chlorosulfonylimino-1,3-dioxolane

cis-4,5-diphenyl-1,3-oxazolidin-2-one

Refernces

• 1、 Zima, Alexandra M.,Lyakin, Oleg Y.,Ottenbacher, Roman V.,Bryliakov, Konstantin P.,Talsi, Evgenii P.. "Iron-Catalyzed Enantioselective Epoxidations with Various Oxidants: Evidence for Different Active Species and Epoxidation Mechanisms". . p. 60 - 69. Retrieved 2017.
• 2、 Notestein, Justin M.,Iglesia, Enrique,Katz, Alexander. "Grafted metallocalixarenes as single-site surface organometallic catalysts". . p. 16478 - 16486. Retrieved 2004.
• 3、 Ostovic, Drazen,Bruice, Thomas C.. "Transition-State Geometry in Epoxidation by Iron-Oxo Porphyrin at the Compound I Oxidation Level. Epoxidation of Alkenes Cyclized by a Sterically Hindered (meso-Tetrakis(2,6-dibromophenyl)porphinato)iron(III) Chloride". . p. 6906 - 6908. Retrieved 1988.
• 4、 Groves,Nemo. "EPOXIDATION REACTIONS CATALYZED BY IRON PORPHYRINS. OXYGEN TRANSFER FROM IODOSYLBENZENE.". . p. 5786 - 5791. Retrieved 1983.
• 5、 Manring, Lewis E.,Peters, Kevin S.. "Picosecond Photochemistry of 2,3-Diphenyloxyranes: Reaction from a Vibrationally Unrelaxed Electronic Excited State". . p. 8077 - 8079. Retrieved 1984.
• 6、 Biswas, Jyoti Prasad,Ansari, Mursaleem,Paik, Aniruddha,Sasmal, Sheuli,Paul, Sabarni,Rana, Sujoy,Rajaraman, Gopalan,Maiti, Debabrata. "Effect of the Ligand Backbone on the Reactivity and Mechanistic Paradigm of Non-Heme Iron(IV)-Oxo during Olefin Epoxidation". supporting information. p. 14030 - 14039. Retrieved 2021/05/11.
• 7、 Ali, K. Ben. "Asymmetric Epoxidation of Unfunctionalized Olefins Using Novel Chiral Dihydroisoquinolinium Salts as Organocatalysts". . p. 638 - 646. Retrieved 2021/06/02.