Diethyl tert-butylmalonate

Base Information

• Chemical Name: Diethyl tert-butylmalonate
• CAS No.: 759-24-0
• Molecular Formula: C11H20 O4
• Molecular Weight: 216.277
• Hs Code.: 2917190090
• European Community (EC) Number: 212-067-5
• NSC Number: 5178
• UNII: Q84FCS2AEB
• DSSTox Substance ID: DTXSID50226819
• Nikkaji Number: J193.121K
• Wikidata: Q83106363
• Mol file: 759-24-0.mol

Synonyms:Diethyl tert-butylmalonate;759-24-0;Diethyl 2-(tert-butyl)malonate;Diethyl t-butylmalonate;diethyl 2-tert-butylpropanedioate;Diethyl (1,1-dimethylethyl)malonate;Diethyl 2-tert-butylmalonate;EINECS 212-067-5;Q84FCS2AEB;NSC-5178;tert-Butylmalonic acid diethyl ester;Propanedioic acid, (1,1-dimethylethyl)-, diethyl ester;UNII-Q84FCS2AEB;SCHEMBL334770;Diethyl 2-tert-butylmalonate #;Diethyl tert-butylmalonate, 96%;DTXSID50226819;NSC5178;NSC 5178;MFCD00009152;1,3-diethyl 2-tert-butylpropanedioate;2-tert-butyl-malonic acid diethyl ester;AS-81555;LS-185545;2-tert-butyl-propanedioic acid diethyl ester;CS-0364853;FT-0624807;1,3-Diethyl 2-(1,1-dimethylethyl)propanedioate;A838552

Chemical Property of Diethyl tert-butylmalonate

Chemical Property:

• Vapor Pressure: 0.102mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 102-104 °C11 mm Hg(lit.)
• PKA: 13.74±0.46(Predicted)
• Flash Point: 195 °F
• PSA: 52.60000
• Density: 1.014 g/mL at 25 °C(lit.)
• LogP: 1.77490
• Water Solubility.: Immiscible with water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 216.13615911
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

97% ^*data from raw suppliers

Diethyl tert-butylmalonate 96% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)OCC)C(C)(C)C
• Uses: Diethyl tert-butylmalonate is used in the preparation of enantiomers of 4-tert-butyl-3-isopropyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-sulfide.

Technology Process of Diethyl tert-butylmalonate

There total 24 articles about Diethyl tert-butylmalonate 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: 93.0%

diethyl isopropylidenemalonate (6802-75-1) + methyl iodide (74-88-4) → tert-butylmalonic acid diethyl ester (759-24-0)

Guidance literature:

methyl iodide; With magnesium; In diethyl ether; at 0 ℃; Inert atmosphere;

diethyl isopropylidenemalonate; With copper(l) chloride; In diethyl ether; for 1.5h; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.tetlet.2016.10.114

Reference yield: 82.0%

diethyl isopropylidenemalonate (6802-75-1) + methyl manganese chloride (89984-56-5) → isopropenyl-malonic acid diethyl ester (38806-12-1) + tert-butylmalonic acid diethyl ester (759-24-0)

Guidance literature:

In tetrahydrofuran; for 2h; Product distribution; 1.) 0 deg C, 2.) 20 deg C; var organomanganeses.;

DOI:10.1016/S0040-4020(01)81312-0

Reference yield: 68.0%

diethyl 1,1-dimethylethyl(methylsulfonyl)malonate (1214319-97-7) → tert-butylmalonic acid diethyl ester (759-24-0)

Guidance literature:

diethyl 1,1-dimethylethyl(methylsulfonyl)malonate; With 1,4-diaza-bicyclo[2.2.2]octane; In toluene; at 20 ℃; for 8h; Reflux;

With water;

DOI:10.1080/00397910902962852

upstream raw materials:

methyl magnesium iodide

diethyl isopropylidenemalonate

t-butyl bromide

diethyl malonate

Downstream raw materials:

4-tert-butyl-1,2-diphenyl-pyrazolidine-3,5-dione

4-tert-butyl-2-phenyl-isoxazolidine-3,5-dione

diethyl (methyl-tert-butyl)malonate

N-phenyl-2-carbethoxy-3,3-dimethylbutyramide