Methyl 3,3-diphenyloxirane-2-carboxylate

Base Information

• Chemical Name: Methyl 3,3-diphenyloxirane-2-carboxylate
• CAS No.: 76527-25-8
• Molecular Formula: C16H14 O3
• Molecular Weight: 254.285
• Hs Code.: 2918990090
• European Community (EC) Number: 616-346-6
• DSSTox Substance ID: DTXSID50442173
• Nikkaji Number: J3.320.264D
• Mol file: 76527-25-8.mol

Synonyms:Methyl 3,3-diphenyloxirane-2-carboxylate;76527-25-8;3,3-Diphenyl-oxiranecarboxylic Acid Methyl Ester;3,3-DIPHENYL-OXIRANE-2-CARBOXYLIC ACID METHYL ESTER;SCHEMBL570250;DTXSID50442173;ILXKNKDKHCSQTL-UHFFFAOYSA-N;AKOS015149669;AS-0366;Methyl3,3-diphenyloxirane-2-carboxylate;AC-28933;methyl 2,3-epoxy-3,3-diphenylpropionate;methyl 3,3-diphenyl-2,3-epoxypropionate;FT-0667676;F16806;A865469;3,3-diphenyloxirane-2-carboxylic acid methyl ester

Chemical Property of Methyl 3,3-diphenyloxirane-2-carboxylate

Chemical Property:

• Melting Point: 56-57℃
• PSA: 38.83000
• LogP: 2.50200
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 254.094294304
• Heavy Atom Count: 19
• Complexity: 309

Purity/Quality:

99% ^*data from raw suppliers

3,3-Diphenyl-oxiranecarboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(O1)(C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Methyl 3,3-diphenyloxirane-2-carboxylate

There total 4 articles about Methyl 3,3-diphenyloxirane-2-carboxylate 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: 94.8%

benzophenone (119-61-9) + methyl chloroacetate (96-34-4) → 3,3-diphenyloxirane-2-carboxylic acid methyl ester (76527-25-8)

Guidance literature:

benzophenone; In toluene; for 0.25h;

With sodium methylate; In toluene; at -10 - -5 ℃; for 0.25h;

methyl chloroacetate; In toluene; at -10 - -5 ℃; for 1.5h;

Reference yield: 65.0%

benzophenone (119-61-9) + dichloroacetic acid methyl ester (116-54-1) → 3,3-diphenyloxirane-2-carboxylic acid methyl ester (76527-25-8)

Guidance literature:

With tris(2,2'-bipyridine)nickel(II) tetrafluoroborate; tetrabutylammomium bromide; zinc dibromide; In dichloromethane; N,N-dimethyl-formamide; Ambient temperature; electrolysis (carbon fiber cathode, zinc rod anode);

DOI:10.1021/jo00006a012

Reference yield:

benzophenone (119-61-9) → 3,3-diphenyloxirane-2-carboxylic acid methyl ester (76527-25-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) from -80 deg C to room temp.

2: CH₂Cl₂

With lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jo00346a013

upstream raw materials:

benzophenone

methyl chloroacetate

diazomethane

3,3-diphenyl-2,3-epoxypropionic acid

Downstream raw materials:

3-(3,4-dimethoxy-phenoxy)-2-hydroxy-3,3-diphenyl-propionic acid methyl ester

2-hydroxy-3,3-diphenyl-3-(2-p-tolyl-ethoxy)-propionic acid methyl ester

3-[2-(4-chloro-phenyl)-ethoxy]-2-hydroxy-3,3-diphenyl-propionic acid methyl ester

2-hydroxy-3-phenethyloxy-3,3-diphenyl-propionic acid methyl ester

Refernces

• 1、 -. "An improved method of preparing Anritsu tezosentan". Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036. . Retrieved 2019/05/04.
• 2、 -. "METHOD FOR PRODUCING (S)-2-HYDROXYPROPANOIC ACID DERIVATIVE". Paragraph 0005; 0039. . Retrieved 2017/12/15.