Diethyl methylmalonate

Base Information

• Chemical Name: Diethyl methylmalonate
• CAS No.: 609-08-5
• Deprecated CAS: 141885-94-1,581796-71-6,581796-71-6
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• Hs Code.: 29171990
• European Community (EC) Number: 210-175-7
• NSC Number: 8700
• UNII: 7KD9S8CQN2
• DSSTox Substance ID: DTXSID0060565
• Nikkaji Number: J43.453A
• Wikidata: Q63395288
• Mol file: 609-08-5.mol

Synonyms:DIETHYL METHYLMALONATE;609-08-5;Diethyl 2-methylmalonate;diethyl 2-methylpropanedioate;Methylmalonic acid diethyl ester;Propanedioic acid, methyl-, diethyl ester;1,3-diethyl 2-methylpropanedioate;Malonic acid, methyl-, diethyl ester;diethyl methylpropanedioate;Ethyl methylmalonate;Ethyl methylmalonate (VAN);2-Methylmalonic acid diethyl;7KD9S8CQN2;2-Methylmalonic acid diethyl ester;NSC 8700;NSC-8700;Propanedioic acid, 2-methyl-, 1,3-diethyl ester;EINECS 210-175-7;2-methyl-propanedioic acid diethyl ester;DIETHYLMETHYLMALONATE;diethyl methyl-malonate;Diethyl2-methylmalonate;diethyl monomethylmalonate;diethyl 2-methyl-malonate;diethyl alpha-methymalonate;UNII-7KD9S8CQN2;diethyl alpha-methylmalonate;Diethyl methylmalonate, 99%;methylmalonic acid diethylester;SCHEMBL141446;DTXSID0060565;AMY4051;Methyl-malonic acid diethyl ester;Methylmalonic acid, diethyl ester;NSC8700;2-methyl-malonic acid diethyl ester;BBL009713;MFCD00009162;STL141078;DIETHYL .ALPHA.-METHYLMALONATE;Methylpropanedioic acid, diethyl ester;AKOS002710243;AS-13122;FT-0624795;FT-0666772;M0366;Propanedioic acid, 2-methyl-, diethyl ester;EN300-21270;D70973;M-4140;Diethyl methylmalonate, puriss., >=99.0% (GC);Q63395288;F0001-1595;Z104494966

Chemical Property of Diethyl methylmalonate

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 204.4 °C at 760 mmHg
• PKA: 13.13±0.46(Predicted)
• Flash Point: 76.7 °C
• PSA: 52.60000
• Density: 1.037 g/cm³
• LogP: 0.74870
• Storage Temp.: Store below +30°C.
• Solubility.: 1000mg/l
• Water Solubility.: immiscible
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 146

Purity/Quality:

98.5%min. ^*data from raw suppliers

Diethyl methylmalonate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)C(C)C(=O)OCC
• Uses: Diethyl methylmalonate is used as intermediate for the syntheses of pharmaceuticals, e.g. non-steroidal anti-inflammatory agents with 2-acrylpropionic acid structures acrylpropionic acid structure. It is also used in the flavour and fragrance industries. Product Data Sheet Diethyl methylmalonate was used to investigate the effect of direct supplementation of the medium with di-ester of methylmalonate on erythromycin fermentation in Saccharopolyspora erythraea mutB strain.

Technology Process of Diethyl methylmalonate

There total 76 articles about Diethyl methylmalonate 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: 98.0%

diethyl malonate (105-53-3) + methyl iodide (74-88-4) → Diethyl methylmalonate (609-08-5)

Guidance literature:

With P(MeNCH₂CH₂)3N; In hexane; acetonitrile; at 25 ℃; for 0.5h;

DOI:10.1021/jo972350i

Reference yield: 97.51%

ethanol (64-17-5) + 2-methylmalononitrile (3696-36-4) → Diethyl methylmalonate (609-08-5)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 60 - 70 ℃;

Reference yield: 91.2%

2-cyanopropanoic acid (632-07-5) + ethanol (64-17-5) → Diethyl methylmalonate (609-08-5)

Guidance literature:

With sulfuric acid; at 20 - 80 ℃; for 4h; Temperature;

upstream raw materials:

methyl bromide

sodium diethylmalonate

diethyl ether

ethyl γ-benzoyl-α-ethoxycarbonyl-α-methyl-β-phenylbutyrate

Downstream raw materials:

2,4-dihydroxy-3,6-dimethylpyridine

2-ethyl-2-methylmalonic acid

diethyl 2-ethyl-2-methylmalonate

2,4-Dihydroxy-3-methyl-chinolin

Refernces

• 1、 Yang, Dan,Wu, Xiong,Zheng, Xiao-Jie,Xie, Jian-Hua,Zhou, Qi-Lin. "Dynamic Kinetic Resolution of I-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters". supporting information. p. 5153 - 5157. Retrieved 2021/07/20.
• 2、 Chan, Wei Chuen,Vinod, Jincy K.,Koide, Kazunori. "Acetal Addition to Electron-Deficient Alkenes with Hydrogen Atom Transfer as a Radical Chain Propagation Step". . p. 3674 - 3682. Retrieved 2021/02/16.