Diethyl malonate

Base Information

• Chemical Name: Diethyl malonate
• CAS No.: 105-53-3
• Deprecated CAS: 145601-68-9
• Molecular Formula: C7H12O4
• Molecular Weight: 160.17
• Hs Code.: 29171910
• European Community (EC) Number: 203-305-9
• ICSC Number: 1739
• NSC Number: 8864
• UN Number: 1993
• UNII: 53A58PA183
• DSSTox Substance ID: DTXSID7021863
• Nikkaji Number: J3.234D
• Wikipedia: Diethyl malonate,Diethyl_malonate
• Wikidata: Q27887610
• RXCUI: 2395765
• Metabolomics Workbench ID: 43914
• ChEMBL ID: CHEMBL177114
• Mol file: 105-53-3.mol

Synonyms:Diethyl propanedioate;Propanedioic acid, diethyl ester;Carbethoxyacetic ester;Dicarbethoxymethane;Methanedicarboxylic acid, diethyl ester;Malonic ester;Malonic acid, diethyl ester;Ethyl Malonate;Propanedioic acid, 1,3-diethyl ester;

Chemical Property of Diethyl malonate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1 mm Hg ( 40 °C)
• Melting Point: -50 °C
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 199.3 °C at 760 mmHg
• PKA: 13.5(at 25℃)
• Flash Point: 100 °C
• PSA: 52.60000
• Density: 1.06 g/cm³
• LogP: 0.50270
• Storage Temp.: Store below +30°C.
• Solubility.: 20.8g/l (External MSDS)
• Water Solubility.: Miscible with ethyl alcohol, ether, chloroform and benzene. Slightly miscible with water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 160.07355886
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99.5% , ^*data from raw suppliers

Diethyl malonate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)CC(=O)OCC
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes.
• Effects of Long Term Exposure: Health effects of the substance have been investigated but none have been found
• Description: As an organic compound, diethyl malonate belongs to the diethyl ester of malonic acid, which is present naturally in guava fruits, melons, grapes, pineapples, blackberries and strawberries as a colorless liquid with an apple-like odor. It is a flavor ingredient commonly found in perfumes, artificial flavorings, alcoholic beverages, various wines and spirits due to its natural pleasant odor. It is also used as an essential intermediate in the syntheses of numerous pharmaceuticals, such as barbiturates, vitamins B1 and B6, non-steroidal anti-inflammatory agents. Besides, diethyl malonate is also involved in organic synthesis of other compounds, such as alpha-aryl malonates, mono-substituted and di-substituted acetic acid. And it can react with benzaldehyde for the production of diethyl benzylidenemalonate in Knoevenagel condensation reaction. Diethyl malonate is a diester derivative of malonic acid, a dicarboxylic acid with two carboxyl groups (-COO-) separated by one methylene group (-CH2-). Diethyl malonate is formed by the replacement of the hydroxyl groups (-OH) of malonic acid with ethoxy groups (-OCH2CH3). The hydrogen atoms on the methylene carbon between the two carboxyl groups make this compound acidic. Because of its unique structure, diethyl malonate is reactive and functions as a reagent for organic synthesis and to make products such as barbiturates, pigments, and agrochemicals. Volatile esters are known to have fruity scents and are often used as fragrances and flavorings. Diethyl malonate is a volatile diester that occurs naturally in fruits such as grapes, strawberries, guava, melon, pineapple, and blackberries.
• uses: Diethyl malonate is the diethyl ester of malonic acid. It naturally occuring in grapes and strawberries, is widely used in the manufacture of pharmaceuticals, antioxidants, and dyes.Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.
• Uses: Diethyl Malonate occurs naturally in grapes and strawberries. It is used in the preparation of barbiturates, artificial flavourings, vitamin B1, and vitamin B6 as well as in perfumes. manufacture of barbiturates. Diethyl malonate is used in organic synthesis for the preparation of alpha-aryl malonates, mono-substituted and di-substituted acetic acid, barbiturates and artificial flavorings. It is also involved in the synthesis of pharmaceuticals like chloroquine, butazolidin and barbital. It acts as intermediate in the synthesis of vitamin B1, vitamin B6, non-steroidal anti-inflammatory agents agrochemicals and perfumes. In Knoevenagel condensation reaction, it reacts with benzaldehyde to get diethyl benzylidenemalonate.

Technology Process of Diethyl malonate

There total 293 articles about Diethyl 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: 86.0%

ethyl 3-oxo-3-(phenylamino)propionate (53341-66-5) → N,N'-diphenylmalonamide (621-10-3) + diethyl malonate (105-53-3)

Guidance literature:

In N,N-dimethyl-formamide; for 5h; Heating;

DOI:10.1016/S0040-4020(01)81765-8

Reference yield: 60.0%

Monothiomalonsaeure-O,O-diethylester (16516-12-4) → diphenyldisulfane (882-33-7) + diethyl malonate (105-53-3)

Guidance literature:

With N-nitrosoacetanilide; In acetone; at 20 ℃; for 20h; Product distribution;

Reference yield: 50.0%

diethyl acetylmalonate (570-08-1) + 4-methoxy-aniline (104-94-9) → 4-methoxyacetanilide (51-66-1) + ethyl 6-methoxy-2-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate (120420-52-2) + diethyl malonate (105-53-3)

Guidance literature:

With hydrogenchloride; 1.)20-100 mg Hg, 45-50 deg C, 16 h 2.)190-220 deg C, 0.5 h;

DOI:10.1007/BF00633172

upstream raw materials:

pyridine

ethanol

diethyl malonoimidate dihydrochloride

2-iodo-propane

Downstream raw materials:

ethyl 2-carbethoxy-3-(2-furanyl)propenoate

2-(1-cyclohexenyl)cyclohexanone

diethyl benzalmalonate

diethyl-2-(4-methoxybenzylidene)malonate

Refernces

• 1、 Tobey,West. "-". . p. 1179,1182. Retrieved 1963.
• 2、 Tuba, Robert,Ungváry, Ferenc. "Octacarbonyl dicobalt-catalyzed selective transformation of ethyl diazoacetate into organic products containing the ethoxycarbonyl carbene building block". . p. 59 - 67. Retrieved 2003.
• 3、 Barton, Derek H. R.,Langlois, Pascal,Okano, Takashi,Ozbalik, Nubar. "An unusual synthesis of malonates". . p. 325 - 326. Retrieved 1990.
• 4、 Morikawa, Satoshi,Yamazaki, Shoko,Furusaki, Yoshiteru,Amano, Naoya,Zenke, Kazumi,Kakiuchi, Kiyomi. "Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: Novel methylenepyrrolidine and methylenetetrahydrofuran syntheses". . p. 3540 - 3544. Retrieved 2006.
• 5、 Parangi, Tarun,Wani, Bina,Chudasama, Uma. "Synthesis of monoesters and diesters using eco-friendly solid acid catalysts - Cerium(IV) and thorium(IV) phosphates". . p. 430 - 438. Retrieved 2013.
• 6、 Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan,Zhao, Lei. "Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents". . . Retrieved 2020.
• 7、 Cheong, Minserk,Kim, Mi-Na,Shim, Ji Yeon. "Rhodium-catalyzed double carbonylation of diiodomethane in the presence of triethylorthoformate". . p. 253 - 255. Retrieved 1996.
• 8、 Rajabi, Fatemeh,Luque, Rafael. "An efficient renewable-derived surfactant for aqueous esterification reactions". . p. 5152 - 5155. Retrieved 2014.
• 9、 He, Xinwei,Shang, Yongjia,Zhou, Yao,Yu, Zhiyu,Han, Guang,Jin, Wenjing,Chen, Jiaojiao. "Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols". . p. 863 - 868. Retrieved 2015.
• 10、 Wasserthal, Lennard K.,Kratzer, Andreas,Hirsch, Andreas. "Sequential fullerenylation of bis-malonates-efficient access to oligoclusters with different fullerene building blocks". . p. 2355 - 2361. Retrieved 2013.