(3R)-2,3-diphenyloxirane

Base Information

• Chemical Name: (3R)-2,3-diphenyloxirane
• CAS No.: 1439-07-2
• Molecular Formula: C14H12O
• Molecular Weight: 196.249
• Hs Code.: 29109000
• European Community (EC) Number: 215-877-7
• Nikkaji Number: J1.170.204J
• Mol file: 1439-07-2.mol

Synonyms:stilbene oxide;stilbene oxide, (2R-trans)-isomer;stilbene oxide, (2S-trans)-isomer;stilbene oxide, (cis)-isomer;stilbene oxide, (trans)-isomer;stilbene oxide, trans-;stilbene oxide, trans-(+-)-isomer;trans-stilbene oxide

Chemical Property of (3R)-2,3-diphenyloxirane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00157mmHg at 25°C
• Melting Point: 65-67 °C(lit.)
• Refractive Index: 1.608
• Boiling Point: 304.5 °C at 760 mmHg
• Flash Point: 133.4 °C
• PSA: 12.53000
• Density: 1.136 g/cm³
• LogP: 3.49920
• Storage Temp.: 2-8°C
• Solubility.: soluble in Toluene
• 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

trans-Stilbene Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

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]2C(O2)C3=CC=CC=C3
• Uses: trans-Stilbene Oxide is used in preparation method of metal complex covalent organic framework material.

Technology Process of (3R)-2,3-diphenyloxirane

There total 439 articles about (3R)-2,3-diphenyloxirane 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: 92.0%

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

Guidance literature:

With [bis(acetoxy)iodo]benzene; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate); In dichloromethane; for 72h; Ambient temperature;

DOI:10.1039/a705109c

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: 76.0%

(E)-1,2-diphenyl-ethene (103-30-0) → benzaldehyde (100-52-7) + (R,R)-trans-stilbene epoxide (1439-07-2)

Guidance literature:

With iodosylbenzene; copper(II) nitrate; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/ja00315a071

upstream raw materials:

cis-stilben

(E)-1,2-diphenyl-ethene

(+)-2-<(S)-N-(α-methylbenzyl)-N-benzylsulfamyl>-3-(pentafluorophenyl)oxaziridine

(1S,2R)-1,2-diphenylethane-1,2-diol

Downstream raw materials:

N-(3-hydroxy-4-methoxybenzyl)-N-methyl-β-hydroxy-α-phenylphenethylamine

Diphenylacetaldehyde

(E)-1,2-diphenyl-ethene

1,2-Diphenylethanol

Refernces

• 1、 Rahman, Sumbul,Santra, Chiranjit,Kumar, Rawesh,Bahadur, Jitendra,Sultana, Asima,Schweins, Ralf,Sen, Debasis,Maity, Sudip,Mazumdar,Chowdhury, Biswajit. "Highly active Ga promoted Co-HMS-X catalyst towards styrene epoxidation reaction using molecular O2". . p. 61 - 68. Retrieved 2014.
• 2、 Yang, Dan,Wang, Xue-Chao,Wong, Man-Kin,Yip, Yiu-Chung,Tang, Man-Wai. "Highly enantioselective epoxidation of trans-stilbenes catalyzed by chiral ketones". . p. 11311 - 11312. Retrieved 1996.
• 3、 Li, Baiyan,Zhang, Yiming,Ma, Dingxuan,Ma, Tianliang,Shi, Zhan,Ma, Shengqian. "Metal-cation-directed de novo assembly of a functionalized guest molecule in the nanospace of a metal-organic framework". . p. 1202 - 1205. Retrieved 2014.
• 4、 Bohe, Luis,Lusinchi, Marie,Lusinchi, Xavier. "Oxygen atom transfer from a chiral oxaziridinium salt. Asymmetric epoxidation of unfunctionalized olefins". . p. 141 - 154. Retrieved 1999.
• 5、 Tang, Yinhai,Gao, Hongyi,Yang, Mu,Wang, Ge,Li, Jie,Zhang, Huan,Tao, Zhang. "NiO promoted CuO-NiO/SBA-15 composites as highly active catalysts for epoxidation of olefins". . p. 8543 - 8548. Retrieved 2016.
• 6、 Wiles, Charlotte,Hammond, Marcus J.,Watts, Paul. "The development and evaluation of a continuous flow process for the lipase-mediated oxidation of alkenes". . . Retrieved 2009.
• 7、 Breau, L.,Durst, T.. "Preparation of Optically Active Epoxides Via Sulfur Ylides. Origin of the Chiral Induction.". . p. 367 - 370. Retrieved 1991.
• 8、 Ahadi, Elahe,Hosseini-Monfared, Hassan,Janiak, Christoph,Spie?, Alex. "Photocatalytic asymmetric epoxidation oftrans-stilbene with manganese-porphyrin/graphene-oxide nanocomposite and molecular oxygen: axial ligand effect". . p. 3290 - 3302. Retrieved 2020.
• 9、 Gibert, Mariona,Ferrer, Marta,Saenchez-Baeza, Francisco,Messeguer, Angel. "Availability and reactivity of concentrated dimethyldioxirane solutions in solvents other than acetone". . p. 8643 - 8650. Retrieved 1997.
• 10、 Huang, Ning,Drake, Hannah,Li, Jialuo,Pang, Jiandong,Wang, Ying,Yuan, Shuai,Wang, Qi,Cai, Peiyu,Qin, Junsheng,Zhou, Hong-Cai. "Flexible and Hierarchical Metal–Organic Framework Composites for High-Performance Catalysis". . p. 8916 - 8920. Retrieved 2018.