Diethyl 2-ethyl-2-methylmalonate

Base Information

• Chemical Name: Diethyl 2-ethyl-2-methylmalonate
• CAS No.: 2049-70-9
• Molecular Formula: C10H18O4
• Molecular Weight: 202.251
• Hs Code.: 2917190090
• European Community (EC) Number: 218-070-8
• UNII: R6V9A28YP8
• DSSTox Substance ID: DTXSID50174462
• Nikkaji Number: J127.716B
• Wikidata: Q83044542
• Mol file: 2049-70-9.mol

Synonyms:2049-70-9;Diethyl 2-ethyl-2-methylmalonate;diethyl 2-ethyl-2-methylpropanedioate;DIETHYL ETHYLMETHYLMALONATE;2-Ethyl-2-methylmalonic Acid Diethyl Ester;1,3-diethyl 2-ethyl-2-methylpropanedioate;R6V9A28YP8;EINECS 218-070-8;Propanedioic acid, 2-ethyl-2-methyl-, 1,3-diethyl ester;ethyl-methyl-malonic acid diethyl ester;Diathylathylmethylmalonat;Propanedioic acid, ethylmethyl-, diethyl ester;UNII-R6V9A28YP8;SCHEMBL7512223;DIETHYL METHYLETHYLMALONATE;DTXSID50174462;Diethyl 2-ethyl-2-methylmalonate #;Ethylmethylmalonic acid diethyl ester;MFCD02258541;AKOS037646629;2-Ethyl-2-methylmalonic acid diethylester;AS-69877;CS-0320717;D3630;D90209

Chemical Property of Diethyl 2-ethyl-2-methylmalonate

Chemical Property:

• Vapor Pressure: 0.151mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• Boiling Point: 217.8 °C at 760 mmHg
• Flash Point: 93.4 °C
• PSA: 52.60000
• Density: 1.008 g/cm³
• LogP: 1.38480
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 202.12050905
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

98%,99%, ^*data from raw suppliers

Diethyl 2-Ethyl-2-methylmalonate ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C(=O)OCC)C(=O)OCC

Technology Process of Diethyl 2-ethyl-2-methylmalonate

There total 17 articles about Diethyl 2-ethyl-2-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: 97.0%

ethyl iodide (75-03-6) + Diethyl methylmalonate (609-08-5) → diethyl 2-ethyl-2-methylmalonate (2049-70-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 100 ℃; for 2h;

DOI:10.1016/j.bmc.2003.08.017

Reference yield: 93.0%

ethene (74-85-1) + sodium diethyl methylmalonate (62116-54-5) → diethyl 2-ethyl-2-methylmalonate (2049-70-9) + ethyl 2-ethoxycarbonyl-2-methyl-3-butenoate (64770-16-7)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); triethylamine; In tetrahydrofuran; Product distribution; multistep reaction: 1.) -78 deg C, 2.) -60 deg C -> room temperature; palladium-assisted alkylation of various olefin with carbanions accompanied by reductive or β-elimination isolation procedure; stereo- and regioselectivity;

DOI:10.1021/ja00535a026

Reference yield: 91.0%

ethyl bromide (74-96-4) + Diethyl methylmalonate (609-08-5) → diethyl 2-ethyl-2-methylmalonate (2049-70-9)

Guidance literature:

Diethyl methylmalonate; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

ethyl bromide; In tetrahydrofuran; at 25 ℃; for 20h;

DOI:10.1016/j.tetasy.2014.11.011

upstream raw materials:

diethyl ether

3-methyl-hexane-2,4,4-tricarboxylic acid triethyl ester

sodium ethanolate

ethyl iodide

Downstream raw materials:

5-ethyl-5-methyl-1H,3H,5H-pyrimidin-2,4,6-trione

ethosuximide

1-bromo-2-methyl-butane

2-ethyl-2-methyl-1,3-propanediol

Refernces

• 1、 Huang, Huan-Ming,Procter, David J.. "Radical Heterocyclization and Heterocyclization Cascades Triggered by Electron Transfer to Amide-Type Carbonyl Compounds". supporting information. p. 14262 - 14266. Retrieved 2017/10/20.
• 2、 Lee, Hyun Soo,Kim, Dong H.. "Synthesis and evaluation of α,α -disubstituted-3-mercaptopropanoic acids as inhibitors for carboxypeptidase A and implications with respect to enzyme inhibitor design". . p. 4685 - 4691. Retrieved 2007/10/03.