Diethyl methyl(phenyl)malonate

Base Information

• Chemical Name: Diethyl methyl(phenyl)malonate
• CAS No.: 34009-61-5
• Molecular Formula: C14H18 O4
• Molecular Weight: 250.295
• Hs Code.: 2917399090
• European Community (EC) Number: 251-789-5
• NSC Number: 147481
• UNII: UU4Q9WA4YZ
• DSSTox Substance ID: DTXSID20187620
• Nikkaji Number: J287.847J
• Wikidata: Q83059325
• Mol file: 34009-61-5.mol

Synonyms:Diethyl methyl(phenyl)malonate;34009-61-5;DIETHYL METHYLPHENYLMALONATE;diethyl 2-methyl-2-phenylpropanedioate;diethyl 2-methyl-2-phenylmalonate;EINECS 251-789-5;NSC-147481;NSC147481;UU4Q9WA4YZ;phenyl methyl diethyl malonate;SCHEMBL2910521;DTXSID20187620;Methylphenylmalonic acid diethyl ester;NSC 147481;Malonic acid, methylphenyl-, diethyl ester;FT-0738401;F78806;Propanedioic acid, methylphenyl-, diethyl ester;Propanedioic acid, 2-methyl-2-phenyl-, 1,3-diethyl ester

Chemical Property of Diethyl methyl(phenyl)malonate

Chemical Property:

• Vapor Pressure: 0.000427mmHg at 25°C
• Melting Point: 156-157 °C (decomp)
• Boiling Point: 315.8°Cat760mmHg
• Flash Point: 148.5°C
• PSA: 52.60000
• Density: 1.092g/cm³
• LogP: 2.07050
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO-d6
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 250.12050905
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

99% ^*data from raw suppliers

DIETHYL METHYLPHENYLMALONATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(C1=CC=CC=C1)C(=O)OCC
• Uses: Diethyl Methylphenylmalonate is an impurity in the synthesis of Heptobarbital (H281165). Heptobarbital is an impurity of Phenobarbital (P316760), which is a controlled substance (depressant), anticonvulsant, sedative and hypnotic.

Technology Process of Diethyl methyl(phenyl)malonate

There total 29 articles about Diethyl methyl(phenyl)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: 98.0%

diethyl 2-phenylmalonate (83-13-6) + methyl iodide (74-88-4) → diethyl 2-methyl-2-phenylmalonate (34009-61-5)

Guidance literature:

diethyl 2-phenylmalonate; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

methyl iodide; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/ja0382361

Reference yield: 95.0%

diphenyliodonium tetrafluoroborate + Diethyl methylmalonate (609-08-5) → diethyl 2-methyl-2-phenylmalonate (34009-61-5)

Guidance literature:

With sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo981065b

Reference yield: 89.0%

bromobenzene (108-86-1,52753-63-6) + diethyl malonate (105-53-3) + methyl iodide (74-88-4) → diethyl 2-methyl-2-phenylmalonate (34009-61-5)

Guidance literature:

bromobenzene; diethyl malonate; With potassium phosphate; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; at 70 ℃; for 10h;

methyl iodide; In toluene; at 70 ℃; for 3h; Further stages.;

DOI:10.1021/jo016226h

upstream raw materials:

diethyl 2-phenylmalonate

methyl iodide

Diethyl methylmalonate

phenyl(p-tolyl)iodonium trifluoromethanesulfonate

Downstream raw materials:

3-methyl-3-phenyl-1H-benz[4,5]imidazo[1,2-a]pyrimidine-2,4-dione

1,5-dimethyl-5-phenyl-pyrimidine-2,4,6-trione

2-(ethylthio)aniline

1-methyl-2-(1-phenylethyl)benzothiazole

Refernces

• 1、 Fan, Rong,Liu, Binbin,Zheng, Tianyu,Xu, Kun,Tan, Chen,Zeng, Tianlong,Su, Shuaisong,Tan, Jiajing. "An aryne triggered ring-opening fluorination of cyclic thioethers with potassium fluoride". supporting information. p. 7081 - 7084. Retrieved 2018/07/05.
• 2、 Yip, Stephanie Y. Y.,A?ssa, Christophe. "Isomerization of olefins triggered by rhodium-catalyzed C-H bond activation: Control of endocyclic β-hydrogen elimination". supporting information. p. 6870 - 6873. Retrieved 2015/06/02.