Diphenyl oxalate

Base Information

• Chemical Name: Diphenyl oxalate
• CAS No.: 3155-16-6
• Molecular Formula: C14H10 O4
• Molecular Weight: 242.231
• Hs Code.: 2917119000
• European Community (EC) Number: 678-315-3
• NSC Number: 400575
• UNII: 7BB9D5HPC2
• DSSTox Substance ID: DTXSID50185452
• Nikkaji Number: J31.422F
• Wikipedia: Diphenyl_oxalate
• Wikidata: Q384334
• ChEMBL ID: CHEMBL1812849
• Mol file: 3155-16-6.mol

Synonyms:Diphenyl oxalate;3155-16-6;Oxalic Acid Diphenyl Ester;Ethanedioic acid, diphenyl ester;OXALIC ACID, DIPHENYL ESTER;1,2-Diphenyl ethanedioate;NSC 400575;BRN 1881259;7BB9D5HPC2;CHEMBL1812849;NSC-400575;4-06-00-00621 (Beilstein Handbook Reference);diphenyloxalate;OXALICACIDDIPHENYLESTER;diphenyl ethanedioate;WLN: ROVVOR;DIPHENYL ETHANEDIOAT;UNII-7BB9D5HPC2;SCHEMBL43364;DTXSID50185452;BDBM50350314;MFCD00059682;NSC400575;STL301834;AKOS016370360;AS-58829;LS-99430;CS-0205159;FT-0764365;O0111;D91801;Q384334

Chemical Property of Diphenyl oxalate

Chemical Property:

• Melting Point: 136°C
• Boiling Point: 336.7°Cat760mmHg
• Flash Point: 147.5°C
• PSA: 52.60000
• Density: 1.257g/cm³
• LogP: 2.19760
• Water Solubility.: Insoluble in water
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 242.05790880
• Heavy Atom Count: 18
• Complexity: 258

Purity/Quality:

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

Diphenyl Oxalate ^*data from reagent suppliers

Safty Information:

• Statements: 22-36/37/38
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC(=O)C(=O)OC2=CC=CC=C2
• Uses: Diphenyl Oxalate is used in preparation of 3,4-dimethylpyrazole-5-carboxylate compound.

Technology Process of Diphenyl oxalate

There total 17 articles about Diphenyl oxalate 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: 69.0%

oxalyl dichloride (79-37-8) + phenol (108-95-2,27073-41-2) → diphenyl oxalate (3155-16-6)

Guidance literature:

With triethylamine; In diethyl ether; at 0 - 25 ℃; for 3.5h;

DOI:10.1002/chem.201301033

Reference yield: 58.0%

phenyl oxalyl chloride (51719-70-1) + phenol (108-95-2,27073-41-2) → diphenyl oxalate (3155-16-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; 1.) 0-5 deg C, 1.5 h, 2.) room temp., 2 h;

DOI:10.1016/S0040-4020(01)81028-0

Reference yield: 40.0%

diisopropenyl oxalate (148705-17-3) + phenol (108-95-2,27073-41-2) → diphenyl oxalate (3155-16-6)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 50 ℃;

DOI:10.1016/S0040-4020(01)86342-0

upstream raw materials:

oxalic acid

phenol

oxalyl dichloride

Dichlor-methoxy-essigsaeure-phenylester

Downstream raw materials:

N,N'-Diphenyloxamid

2-((phenylamino)methyl)phenol

N,N'-bis(4-methoxyphenyl) oxamide

N-(2-hydroxybenzyl)-p-anisidine

Refernces

• 1、 Barbosa, Sandro L.,Ottone, Myrlene,De Freitas, Milton,Lima, Camila D.,Nelson, David L.,Clososki, Giuliano C.,Caires, Franco J.,Klein, Stanlei I.,Hurtado, Gabriela R.. "Synthesis of phenyl esters using SiO2-SO3H catalyst in conventional heating and microwave-irradiated esterification processes". . p. 3663 - 3668. Retrieved 2019/05/08.
• 2、 Gruenberg, Matthias F.,Goossen, Lukas J.. "Synthesis of arylacetates from benzylic alcohols and oxalate esters through decarboxylative coupling". supporting information. p. 7334 - 7337. Retrieved 2013/06/27.