Dimethyl oxalate

Base Information

• Chemical Name: Dimethyl oxalate
• CAS No.: 553-90-2
• Molecular Formula: C4H6O4
• Molecular Weight: 118.089
• Hs Code.: 2917 11 00
• European Community (EC) Number: 209-053-6
• NSC Number: 9374
• UNII: IQ3Q79344S
• DSSTox Substance ID: DTXSID9060287
• Nikkaji Number: J2.653K
• Wikipedia: Dimethyl oxalate
• Wikidata: Q412931
• Metabolomics Workbench ID: 67614
• Mol file: 553-90-2.mol

Synonyms:Dimethyl oxalate;553-90-2;METHYL OXALATE;Oxalic acid dimethyl ester;Ethanedioic acid, dimethyl ester;Oxalic acid, dimethyl ester;dimethyl ethanedioate;NSC 9374;EINECS 209-053-6;UNII-IQ3Q79344S;AI3-21214;IQ3Q79344S;NSC-9374;Ethanedioic acid, 1,2-dimethyl ester;Dimethyl ester of oxalic acid;MFCD00008442;Oxalic acid dimethyl;SCHEMBL8295;METHYL OXALATE [MI];CHEBI:6859;DIMETHYL OXALATE [INCI];DTXSID9060287;NSC9374;AMY37133;BBL011507;Ethanedioic acid 1,2-dimethyl ester;STL146620;AKOS000269022;Dimethyl oxalate, ReagentPlus(R), 99%;AS-12646;LS-99429;FT-0625150;O0080;EN300-20093;E78838;Dimethyl oxalate, Vetec(TM) reagent grade, 98%;A830619;Q412931;Q-200995;F0001-1452

Chemical Property of Dimethyl oxalate

Chemical Property:

• Appearance/Colour: Colourless crystal
• Vapor Pressure: 2.06mmHg at 25°C
• Melting Point: 50-54 °C(lit.)
• Refractive Index: n20/D 1.39(lit.)
• Boiling Point: 163.5 °C at 760 mmHg
• Flash Point: 75 °C
• PSA: 52.60000
• Density: 1.163 g/cm³
• LogP: -0.66760
• Storage Temp.: Store below +30°C.
• Solubility.: ethanol: soluble50mg/mL, clear to very slightly hazy, colorless
• Water Solubility.: 60 G/L (25 ºC)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 118.02660867
• Heavy Atom Count: 8
• Complexity: 92.6

Purity/Quality:

98% ^*data from raw suppliers

Dimethyl Oxalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/38-36-22
• Safety Statements: 26-36/37-24/25-23

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)C(=O)OC
• Description: Dimethyl oxalate is a chemical compound with formula (CH3)2(COO)2. It is the dimethyl ester of oxalic acid.
• Uses: Dimethyl oxalate is used as an alternate fuel in the direct oxidation fuel cell. It is involved in the catalytic hydrogenation using Cu/SiO22ub> to prepare ethylene glycol. It is also used in the selective gas-phase hydrogenation catalyzed by Ag/SiO2 to get the corresponding alcohol.

Technology Process of Dimethyl oxalate

There total 126 articles about Dimethyl 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: 95.0%

diethyl phosphorylchloridite (589-57-1) + methyl 2,2-dichloro-2-methoxyacetate (17640-25-4) → monomethyl oxalyl chloride (5781-53-3) + Dimethyl oxalate (553-90-2) + chloroethane (75-00-3) + phosphonic dichloride (66298-75-7) + methyl phosphonochloridate (74813-29-9) + ethyl phosphonochloridate (74813-30-2)

Guidance literature:

With iron(III) chloride; at 105 - 110 ℃; for 1.16667h; Product distribution;

Reference yield: 85.0%

cis-(methyloxalyl)(methoxycarbonyl)tetracarbonyliron → Dimethyl oxalate (553-90-2) + iron pentacarbonyl (13463-40-6,37220-42-1) + bis(methoxycarbonyl)tetracarbonyliron

Guidance literature:

In dichloromethane-d2; byproducts: CO; introducing a soln. of Fe-complex in CD2Cl2 into NMR tube, maintaining temp. at 28°C under N2; monitoring by (13)C-NMR and gas chromatography;

DOI:10.1016/0022-328X(94)88044-1

Reference yield:

methanol (67-56-1) + 4-chloro-phenol (106-48-9,82344-39-6) → Dimethyl oxalate (553-90-2) + (R)-dimethyl malate (70681-41-3) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + malonic acid dimethyl ester (108-59-8)

Guidance literature:

4-chloro-phenol; In water; at 20 ℃; Darkness;

With dihydrogen peroxide; In water; Irradiation;

methanol; With sulfuric acid; Reflux;

DOI:10.1016/j.molcata.2013.01.022

upstream raw materials:

diazomethane

phenol; compound with oxalic acid

oxalic acid

methanol

Downstream raw materials:

N,N'-bis-benzenesulfonyl-oxalamide

benzenesulfonyl-oxalamic acid methyl ester

p-methylanizole

(4-chloro-benzenesulfonyl)-oxalamic acid methyl ester

Refernces

• 1、 Mooibroek, Tiddo J.,Bouwman, Elisabeth,Drent, Eite. "Mechanistic study of the oxidative carbonylation of methanol catalyzed by palladium diphosphane complexes with nitrobenzene as oxidant". . p. 1403 - 1412. Retrieved 2012.
• 2、 Guo, Guo-Cong,Jing, Kai-Qiang,Tan, Hong-Zi,Wang, Zhi-Qiao,Xu, Yu-Ping,Xu, Zhong-Ning. "Lewis acid sites in MOFs supports promoting the catalytic activity and selectivity for CO esterification to dimethyl carbonate". . p. 1699 - 1707. Retrieved 2020.
• 3、 Kevill, Dennis N.,Park, Byoung-Chun,Kyong, Jin Burm. "A kinetic study of the solvolyses of methyl and ethyl chloroglyoxalates". . p. 9032 - 9035. Retrieved 2005.
• 4、 Cavinato, G.,Toniolo, L.. "New aspects of the synthesis of dimethyl carbonate via carbonylation of methyl alcohol promoted by methoxycarbonyl complexes of palladium(II)". . p. C65 - C66. Retrieved 1993.
• 5、 Peng, Si-Yan,Xu, Zhong-Ning,Chen, Qing-Song,Wang, Zhi-Qiao,Chen, Yumin,Lv, Dong-Mei,Lu, Gang,Guo, Guo-Cong. "MgO: An excellent catalyst support for CO oxidative coupling to dimethyl oxalate". . p. 1925 - 1930. Retrieved 2014.
• 6、 Huang, Zhimei,Zeng, Haipeng,Xie, Meilan,Lin, Xing,Huang, Zhaoming,Shen, Yue,Huang, Yunhui. "A Stable Lithium–Oxygen Battery Electrolyte Based on Fully Methylated Cyclic Ether". . p. 2345 - 2349. Retrieved 2019.
• 7、 Amadio, Emanuele,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.,Toniolo, Luigi. "Palladium catalyzed oxidative carbonylation of alcohols: Effects of diphosphine ligands". . p. 2856 - 2864. Retrieved 2015.
• 8、 Peng, Si-Yan,Xu, Zhong-Ning,Chen, Qing-Song,Chen, Yu-Min,Sun, Jing,Wang, Zhi-Qiao,Wang, Ming-Sheng,Guo, Guo-Cong. "An ultra-low Pd loading nanocatalyst with high activity and stability for CO oxidative coupling to dimethyl oxalate". . p. 5718 - 5720. Retrieved 2013.
• 9、 Olofson et al.. "". . p. 6554. Retrieved 1968.
• 10、 Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong. "Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis". supporting information. p. 513 - 523. Retrieved 2021/01/12.