trans-Stilbene oxide

Base Information

• Chemical Name: trans-Stilbene oxide
• CAS No.: 25144-18-7
• Molecular Formula: C₁₄H₁₂O
• Molecular Weight: 196.249
• European Community (EC) Number: 215-877-7
• NSC Number: 100317,40295
• UNII: LIG187ZROD
• DSSTox Substance ID: DTXSID301315411
• Nikkaji Number: J1.007C
• Wikidata: Q27121648
• Metabolomics Workbench ID: 57297
• ChEMBL ID: CHEMBL1743221
• Mol file: 25144-18-7.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 trans-Stilbene oxide

Chemical Property:

• Melting Point: 62 °C
• Boiling Point: 304.5°Cat760mmHg
• Flash Point: 133.4°C
• Density: 1.136g/cm³
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Benzene (Slightly, Sonicated), Chloroform (Slightly)
• 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:

(2R,3R)-2,3-Diphenyloxirane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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]2[C@H](O2)C3=CC=CC=C3
• Recent ClinicalTrials: TSO in Pediatric Autistic Spectrum Disorders
• Recent EU Clinical Trials: Probiotic Treatment of Ulcerative Colitis with Trichuris suis ova (TSO)
• Uses: (2R,3R)-2,3-Diphenyloxirane is a potent inducer of liver miscrosomal cytochrome P 450-dependent monooxygenases. Studies show that (2R,3R)-2,3-Diphenyloxirane is more potent than its (-)-enantiomer.

Technology Process of trans-Stilbene oxide

There total 171 articles about trans-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: 81.0%

2,5-diphenyl-[1,3]dioxolan-4-one (56535-98-9) → 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:

at 650 ℃;

DOI:10.1021/ja00408a022

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: 61.0%

(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) + benzil (134-81-6) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With 12C₂₅H₅₄N⁽¹⁺⁾*{ZnWCu₂(NO)2(ZnW₉O₃₄)2}^(12-); oxygen; In acetonitrile; for 5h; under 1500.15 Torr;

upstream raw materials:

methanol

cis-stilben

(E)-1,2-diphenyl-ethene

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

Downstream raw materials:

3-Nonyl-5,6-diphenyl-[1,2,4]trioxane

(1S,2R)-1,2-Diphenyl-2-((R)-1-phenyl-propylamino)-ethanol

3,6-diphenyl-1,2,4,5-tetraoxane

3,5,6-Triphenyl-[1,2,4]trioxane

Refernces

• 1、 Yari, Omolbanin,Elhamifar, Dawood,Shaker, Masoumeh. "Self-assembled ionic liquid based organosilica-titania: A novel and efficient catalyst for green epoxidation of alkenes". . . Retrieved 2021/04/06.
• 2、 Bouzari, Narges,Bezaatpour, Abolfazl,Babaei, Behnam,Amiri, Mandana,Boukherroub, Rabah,Szunerits, Sabine. "Modification of MnFe2O4 surface by Mo (VI) pyridylimine complex as an efficient nanocatalyst for (ep)oxidation of alkenes and sulfides". . . Retrieved 2021/03/04.