Dimethyl malonate

Base Information

• Chemical Name: Dimethyl malonate
• CAS No.: 108-59-8
• Molecular Formula: C5H8O4
• Molecular Weight: 132.116
• Hs Code.: 29171910
• European Community (EC) Number: 203-597-8
• NSC Number: 620046
• UNII: EM8Y79998C
• DSSTox Substance ID: DTXSID4029145
• Nikkaji Number: J1.499K
• Wikipedia: Dimethyl_malonate
• Wikidata: Q4263082
• Metabolomics Workbench ID: 125983
• ChEMBL ID: CHEMBL1986332
• Mol file: 108-59-8.mol

Synonyms:dimethyl malonate;methyl malonate

Chemical Property of Dimethyl malonate

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.000135mmHg at 25°C
• Melting Point: -62 °C(lit.)
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 177.1 °C at 760 mmHg
• PKA: 11.80±0.46(Predicted)
• Flash Point: 90 °C
• PSA: 52.60000
• Density: 1.156 g/cm³
• LogP: -0.27750
• Storage Temp.: Store below +30°C.
• Solubility.: alcohol: miscible
• Water Solubility.: negligible
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

99% ^*data from raw suppliers

Methylmalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)CC(=O)OC
• Recent ClinicalTrials: The Role of Mitochondrial Respiration in the Cardioprotective Capacity of IPC in Diabetic and Non-diabetic Patients
• Description: Dimethyl malonate is a diester derivative of malonic acid. It is a common reagent for organic synthesis used, for example, as a precursor for barbituric acid. It is also used in the malonic ester synthesis. It can be synthesized from dimethoxymethane and carbon monoxide.
• Uses: It is used in fragrances and some artificial flavorings . Dimethyl malonate is a reagent used in organic synthesis. It acts as a precursor for the synthesis of mono-substituted and di-substituted acetic acid, barbiturates, vitamin B1 and vitamin B6. It is used in the pharmaceutical industry to prepare pharmaceuticals like chloroquine and butazolidin. It is involved in the synthesis of diastereomeric pure thienylpyridines by reacting with 1,3-diphenylprop-2-enyl acetate.

Technology Process of Dimethyl malonate

There total 117 articles about Dimethyl malonate 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:

cis-(CO)4Fe(COOMe)(CH2COOMe) → iron pentacarbonyl (13463-40-6,37220-42-1) + malonic acid dimethyl ester (108-59-8)

Guidance literature:

With carbon monoxide; Co atmosphere, 30°C, 3 h;

DOI:10.1039/c39880000929

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

Reference yield:

bromo-(3-oxo-1,3-diphenyl-propyl)-malonic acid dimethyl ester → 2,3-dibromo-1,3-diphenylpropane-1-one (611-91-6) + malonic acid dimethyl ester (108-59-8)

Guidance literature:

at 200 - 225 ℃;

upstream raw materials:

methanol

malonic acid

sodium cyanoacetate

diethyl ether

Downstream raw materials:

2-(benzoylamino-phenyl-methyl)-malonic acid dimethyl ester

Tetramethyl ethylenetetracarboxylate

dimethyl 2-(2-chlorobenzylidene)propanedioate

dimethyl 2-(phenyl(phenylamino)methyl)malonate

Refernces

• 1、 Hall,Caille,Drouin,Lamothe,Muller,Deslongchamps. "A stereospecific transannular Diels-Alder approach to the [6.6.7] tricyclic skeleton related to aphidicolin and scopadulan natural products". . p. 1081 - 1088. Retrieved 1995.
• 2、 Kondo, Tadao,Nakane, Yukari,Tamura, Hirotoshi,Goto, Toshio,Eugster, C.H.. "STRUCTURE OF MONARDAEIN, A BIS-MALONYLATED ANTHOCYANIN ISOLATED FROM GOLDEN BALM, MONARDA DIDYMA". . p. 5879 - 5882. Retrieved 1985.
• 3、 Laurent, Pascale,Sabo-Etienne, Sylviane,Larsonneur, Anne-Marie,Abbayes, Herve des. "Synthesis of Alkyl(alkoxycarbonyl)tetracarbonyliron Complexes : the First Evidence of their Relevance to the Catalytic Cycle in the Carbonylation of Organic Halides induced by Pentacarbonyliron". . p. 929 - 930. Retrieved 1988.
• 4、 Soulen,Paul. "-". . p. 261,263, 268. Retrieved 1977.
• 5、 Shinoda, Kiyonori,Yasuda, Kensei. "VAPOR PHASE CARBONYLATION OF METHYL CHLOROACETATE". . p. 9 - 10. Retrieved 1985.
• 6、 Reznikov,Skvortsov. "Catalytic hydrophosphorylation of dialkyl 2-allylmalonates". . p. 1170 - 1176. Retrieved 2007.
• 7、 Oreshko, G. V.,Lagodzinskaya, G. V.,Eremenko, L. T.. "SYNTHESIS OF ESTERS OF 3-FLUORO-3-NITROACRYLIC ACID". . p. 635 - 637. Retrieved 1989.
• 8、 El-Tabl, Abdou S.,Wahed, Moshira M. Abd-El,Mohamed, Eman A,Abu-Setta, Mohammed H. H.. "Modulation of cancer therapy using nano-organometallic compounds: Preparation, spectroscopic characterization and cytotoxic evaluation". . p. 3873 - 3887. Retrieved 2021/07/17.
• 9、 Ou, Wei,Zou, Ru,Han, Mengting,Yu, Lei,Su, Chenliang. "Tailorable carbazolyl cyanobenzene-based photocatalysts for visible light-induced reduction of aryl halides". supporting information. p. 1899 - 1902. Retrieved 2019/12/27.