Diemethyl oxalate


  • English nameDiemethyl oxalate
  • CAS number553-90-2
  • Molecular formulaC4H6O4
  • Molecular weight118.089
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  • appearanceColourless crystal
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Factory Sells Best Quality Diemethyl oxalate 553-90-2 with USP

  • Molecular Formula:C4H6O4
  • Molecular Weight:118.089
  • 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 

Dimethyl oxalate(Cas 553-90-2) Usage

Chemical Description

Dimethyl oxalate is an organic compound with the formula (CH3O2C)2.

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 261, 1959 DOI: 10.1021/jo01084a633

Purification Methods

Crystallise the ester repeatedly from EtOH. De-gas it under nitrogen at high vacuum and distil it. [Beilstein 2 IV 1847.]

General Description

Dimethyl oxalate undergoes Cu/SiO2 catalyzed hydrogenation to yield ethylene glycol. It undergoes selective gas-phase hydrogenation catalyzed by Ag/SiO2 to yield corresponding alcohol.

InChI:InChI=1/C4H6O4/c1-7-3(5)4(6)8-2/h1-2H3

553-90-2 Relevant articles

Cyclization of Dimethyl Oxalate upon Electron Impact

Liehr, J. G.,Larka, E. A.,Beynon, J. H.

, p. 34 - 36 (1981)

Isotope labelling experiments and also c...

Mechanistic study of the oxidative carbonylation of methanol catalyzed by palladium diphosphane complexes with nitrobenzene as oxidant

Mooibroek, Tiddo J.,Bouwman, Elisabeth,Drent, Eite

, p. 1403 - 1412 (2012)

The reactivity of Pd complexes having bi...

Catalytic Synthesis of Oxalate Esters

Current, Steven P.

, p. 1779 - 1780 (1983)

A new catalyst system, palladium(II) ace...

Lewis acid sites in MOFs supports promoting the catalytic activity and selectivity for CO esterification to dimethyl carbonate

Guo, Guo-Cong,Jing, Kai-Qiang,Tan, Hong-Zi,Wang, Zhi-Qiao,Xu, Yu-Ping,Xu, Zhong-Ning

, p. 1699 - 1707 (2020)

CO esterification to dimethyl carbonate ...

Catalyst design criteria and fundamental limitations in the electrochemical synthesis of dimethyl carbonate

?ari?, Manuel,Davies, Bethan Jane Venceslau,Schj?dt, Niels Christian,Dahl, S?ren,Moses, Poul Georg,Escudero-Escribano, María,Arenz, Matthias,Rossmeisl, Jan

, p. 6200 - 6209 (2019)

Dimethyl carbonate is an environmentally...

A kinetic study of the solvolyses of methyl and ethyl chloroglyoxalates

Kevill, Dennis N.,Park, Byoung-Chun,Kyong, Jin Burm

, p. 9032 - 9035 (2005)

Solvolyses of methyl and ethyl chlorogly...

Remarkable Decrease in Overpotential of Oxalate Formation in Electrochemical CO2 Reduction by a Metal-Sulfide Cluster

Kushi, Yoshinori,Nagao, Hirotaka,Nishioka, Takanori,Isobe, Kiyoshi,Tanaka, Koji

, p. 1223 - 1224 (1995)

Triangular metal-sulfide cluster, 3(μ3-S...

New aspects of the synthesis of dimethyl carbonate via carbonylation of methyl alcohol promoted by methoxycarbonyl complexes of palladium(II)

Cavinato, G.,Toniolo, L.

, p. C65 - C66 (1993)

suspended in MeOH reacts with carbon mo...

Active Pd(II) complexes: Enhancing catalytic activity by ligand effect for carbonylation of methyl nitrite to dimethyl carbonate

Tan, Hong-Zi,Wang, Zhi-Qiao,Xu, Zhong-Ning,Sun, Jing,Chen, Zhe-Ning,Chen, Qing-Song,Chen, Yumin,Guo, Guo-Cong

, p. 3785 - 3790 (2017)

Palladium (Pd)-based catalysts have been...

MgO: An excellent catalyst support for CO oxidative coupling to dimethyl oxalate

Peng, Si-Yan,Xu, Zhong-Ning,Chen, Qing-Song,Wang, Zhi-Qiao,Chen, Yumin,Lv, Dong-Mei,Lu, Gang,Guo, Guo-Cong

, p. 1925 - 1930 (2014)

Pd/MgO catalysts are found, for the firs...

Low-temperature synthesis of α-alumina nanosheets on microfibrous-structured Al-fibers for Pd-catalyzed CO oxidative coupling to dimethyl oxalate

Wang, Chunzheng,Xu, Weisong,Qin, Zhengxing,Liu, Xinmei,Mintova, Svetlana

, p. 158 - 166 (2020)

We reported the low-temperature synthesi...

A Stable Lithium–Oxygen Battery Electrolyte Based on Fully Methylated Cyclic Ether

Huang, Zhimei,Zeng, Haipeng,Xie, Meilan,Lin, Xing,Huang, Zhaoming,Shen, Yue,Huang, Yunhui

, p. 2345 - 2349 (2019)

Ether-based electrolytes are commonly us...

Selectivity Control of Carbonylation of Methanol to Dimethyl Oxalate and Dimethyl Carbonate over Gold Anode by Electrochemical Potential

Funakawa, Akiyasu,Yamanaka, Ichiro,Takenaka, Sakae,Otsuka, Kiyoshi

, p. 5346 - 5347 (2004)

New and unique electrocatalysis of gold ...

Palladium catalyzed oxidative carbonylation of alcohols: Effects of diphosphine ligands

Amadio, Emanuele,Freixa, Zoraida,Van Leeuwen, Piet W. N. M.,Toniolo, Luigi

, p. 2856 - 2864 (2015)

The catalytic activity of a series of pa...

-

Friess,Miller

, p. 2611 (1950)

-

An ultra-low Pd loading nanocatalyst with high activity and stability for CO oxidative coupling to dimethyl oxalate

Peng, Si-Yan,Xu, Zhong-Ning,Chen, Qing-Song,Chen, Yu-Min,Sun, Jing,Wang, Zhi-Qiao,Wang, Ming-Sheng,Guo, Guo-Cong

, p. 5718 - 5720 (2013)

A Pd/α-Al2O3 nanocatalyst with ultra-low...

New series of γ-pyrone based podands: Synthesis, characterization and study of their application in acetate salts cation trapping for nucleophilic substitution reactions

Teimuri-Mofrad, Reza,Aghaiepour, Alireza,Rahimpour, Keshvar

, p. 121 - 132 (2019)

Dialkyl 4-oxo-4H-pyran-2,6-dicarboxylate...

Pd/Mg(OH)2 Heterogeneous Nanocatalysts Synthesized by a Facile One-Pot Hydrothermal Method for CO Direct Esterification to Dimethyl Oxalate

Lin, Xiao-Qi,Wang, Zhi-Qiao,Xu, Zhong-Ning,Guo, Guo-Cong

, p. 3213 - 3219 (2021)

Pd-based heterogeneous nanocatalysts hav...

Dynamic Kinetic Cross-Electrophile Arylation of Benzyl Alcohols by Nickel Catalysis

Guo, Peng,Wang, Ke,Jin, Wen-Jie,Xie, Hao,Qi, Liangliang,Liu, Xue-Yuan,Shu, Xing-Zhong

supporting information, p. 513 - 523 (2021/01/12)

Catalytic transformation of alcohols via...

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

Wu, Dehua,Song, Jintong,Qu, Lang,Zhou, Weilan,Wang, Lei,Zhou, Xiangge,Xiang, Haifeng

supporting information, p. 3370 - 3378 (2020/10/02)

The simpler, the better. A series of sim...

553-90-2 Process route

cis-(methyloxalyl)(methoxycarbonyl)tetracarbonyliron

cis-(methyloxalyl)(methoxycarbonyl)tetracarbonyliron

Dimethyl oxalate
553-90-2

Dimethyl oxalate

iron pentacarbonyl
13463-40-6,37220-42-1

iron pentacarbonyl

bis(methoxycarbonyl)tetracarbonyliron

bis(methoxycarbonyl)tetracarbonyliron

Conditions
Conditions Yield
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;
85%
15%
With carbon monoxide; In dichloromethane-d2; introducing a soln. of Fe-complex in CH2Cl2 into an autoclave thermostated at 34°C, stirring for 2.5 h under CO pressure; monitoring by (13)C-NMR and gas chromatography, cooling, removal of solvent under vacuum, redissolution in CD2Cl2, monitoring by (13)C-NMR;
 
methanol
67-56-1

methanol

4-chloro-phenol
106-48-9,82344-39-6

4-chloro-phenol

Dimethyl oxalate
553-90-2

Dimethyl oxalate

(R)-dimethyl malate
70681-41-3

(R)-dimethyl malate

dimethyl cis-but-2-ene-1,4-dioate
624-48-6

dimethyl cis-but-2-ene-1,4-dioate

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

Conditions
Conditions Yield
4-chloro-phenol; In water; at 20 ℃; Darkness;
With dihydrogen peroxide; In water; Irradiation;
methanol; With sulfuric acid; Reflux;
 

553-90-2 Upstream products

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    186581-53-3

    diazomethane

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    66775-86-8

    phenol; compound with oxalic acid

  • 144-62-7
    144-62-7

    oxalic acid

  • 67-56-1
    67-56-1

    methanol

553-90-2 Downstream products

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    91101-02-9

    (5,5-dimethyl-2-oxo-tetrahydro-[3]furyl)-glyoxylic acid ethyl ester

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    4083-65-2

    N,N'-bis-benzenesulfonyl-oxalamide

  • 90668-97-6
    90668-97-6

    benzenesulfonyl-oxalamic acid methyl ester

  • 104-93-8
    104-93-8

    p-methylanizole

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