Diethyl phenylmalonate

Base Information

• Chemical Name: Diethyl phenylmalonate
• CAS No.: 83-13-6
• Molecular Formula: C13H16O4
• Molecular Weight: 236.268
• Hs Code.: 29173980
• European Community (EC) Number: 201-456-5
• NSC Number: 53560,8126
• UNII: XVQ6PE5CLT
• DSSTox Substance ID: DTXSID7058886
• Nikkaji Number: J136.571A
• Wikipedia: Diethyl_phenylmalonate
• Wikidata: Q18351725
• Mol file: 83-13-6.mol

Synonyms:Diethyl phenylmalonate;83-13-6;Diethyl 2-phenylmalonate;Propanedioic acid, phenyl-, diethyl ester;Phenylmalonic acid diethyl ester;diethyl 2-phenylpropanedioate;DIETHYLPHENYLMALONATE;1,3-diethyl 2-phenylpropanedioate;XVQ6PE5CLT;MFCD00009144;Malonic acid, phenyl-, diethyl ester;EINECS 201-456-5;NSC 53560;NSC-53560;AI3-07022;Ethyl phenylmalonate;diethylphenylmalonat-;diethyl-phenylmalonate;UNII-XVQ6PE5CLT;PhCH(CO2Et)2;CBMicro_047868;Diethyl 2-phenylmalonate #;Diethyl phenylmalonate, 98%;SCHEMBL266419;DTXSID7058886;phenyl-malonic acid diethyl ester;NSC8126;NSC-8126;NSC53560;2-Phenyl-malonic acid diethyl ester;AKOS003671792;2-phenyl-propanedioic acid diethyl ester;AC-19988;AS-14253;SY033136;BIM-0047923.P001;CS-0036888;FT-0624800;P0311;EN300-85265;W18251;A840510;Propanedioic acid, 2-phenyl-, 1,3-diethyl ester;SR-01000196305;Q-200976;SR-01000196305-1;Q18351725;F0001-2125;2-ethyl-2-(2-ethylphenyl)propanedioate;Diethyl 2-Phenylmalonate

Chemical Property of Diethyl phenylmalonate

Chemical Property:

• Appearance/Colour: clear colourless to yellowish liquid after melting
• Vapor Pressure: 0.00108mmHg at 25°C
• Melting Point: 16 °C
• Refractive Index: n20/D 1.491(lit.)
• Boiling Point: 301 °C at 760 mmHg
• PKA: 11.84±0.46(Predicted)
• Flash Point: 141.8 °C
• PSA: 52.60000
• Density: 1.111 g/cm³
• LogP: 1.89640
• Storage Temp.: Store below +30°C.
• Water Solubility.: immiscible
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 236.10485899
• Heavy Atom Count: 17
• Complexity: 238

Purity/Quality:

99% ^*data from raw suppliers

Diethyl Phenylmalonate ^*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(C1=CC=CC=C1)C(=O)OCC
• Uses: Diethyl phenylmalonate was used in the synthesis of felbamate-d4 (2-phenyl-1,3-propanediol-l,l,3,3-d4 dicarbamate) using lithium aluminum deuteride.

Technology Process of Diethyl phenylmalonate

There total 51 articles about Diethyl phenylmalonate 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: 100.0%

iodobenzene (591-50-4) + diethyl malonate (105-53-3) → diethyl 2-phenylmalonate (83-13-6)

Guidance literature:

With barium dihydroxide; sodium tetrachloropalladate(II); In N,N-dimethyl acetamide; at 100 ℃; for 14h;

DOI:10.1016/S0040-4039(02)00314-3

Reference yield: 93.0%

chlorobenzene (108-90-7) + diethyl malonate (105-53-3) → diethyl 2-phenylmalonate (83-13-6)

Guidance literature:

With barium dihydroxide; sodium tetrachloropalladate(II); In N,N-dimethyl acetamide; at 100 ℃; for 14h;

DOI:10.1016/S0040-4039(02)00314-3

Reference yield: 92.0%

Ethyl 2-phenylethanoate (101-97-3) → diethyl 2-phenylmalonate (83-13-6)

Guidance literature:

With polystyrene-trityllithium; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/ja00415a034

upstream raw materials:

tetrachloromethane

ethyl 2-diazo-3-oxo-3-phenylpropanoate

2-oxo-3-phenylbutanedioic acid diethyl ester

Ethyl 2-phenylethanoate

Downstream raw materials:

phenyl-acetic acid-(2-piperidino-ethyl ester)

1-ethyl-2-(1-methyl-[4]piperidyl)-4-phenyl-pyrazolidine-3,5-dione

1-isopropyl-2-(1-methyl-piperidin-4-yl)-4-phenyl-pyrazolidine-3,5-dione

1-(1-butyl-[4]piperidyl)-4-phenyl-pyrazolidine-3,5-dione

Refernces

• 1、 Aramendía, María A.,Borau, Victoriano,Jiménez, César,Marinas, José M.,Ruiz, José R.,Urbano, Francisco J.. "α-Arylation of diethyl malonate via enolate with bases in a heterogeneous phase". . p. 2847 - 2849. Retrieved 2002.
• 2、 Lee, Boran,Chirik, Paul J.. "Ketone Synthesis from Benzyldiboronates and Esters: Leveraging α-Boryl Carbanions for Carbon-Carbon Bond Formation". supporting information. p. 2429 - 2437. Retrieved 2020/03/03.
• 3、 Garnier, Tony,Danel, Mathieu,Magné, Valentin,Pujol, Anthony,Bénéteau, Valérie,Pale, Patrick,Chassaing, Stefan. "Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis". . p. 6408 - 6422. Retrieved 2018/05/31.