Diethyl 2-(4-fluorophenyl)malonate

Base Information

• Chemical Name: Diethyl 2-(4-fluorophenyl)malonate
• CAS No.: 2965-90-4
• Molecular Formula: C13H15FO4
• Molecular Weight: 254.258
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID20382193
• Nikkaji Number: J1.368.675K
• Wikidata: Q72461942
• Mol file: 2965-90-4.mol

Synonyms:Diethyl 2-(4-fluorophenyl)malonate;2965-90-4;Diethyl 2-(4-fluorophenyl)propanedioate;Diethyl 4-fluorophenyl malonate;MFCD04039208;DIETHYL-4-FLUOROPHENYL MALONATE;1,3-diethyl 2-(4-fluorophenyl)propanedioate;SCHEMBL1772316;diethyl (4-fluorophenyl)malonate;DTXSID20382193;QHPZGTQIXUSMBA-UHFFFAOYSA-N;AMY19328;CAA96590;BBL102877;diethyl (4-fluorophenyl)propanedioate;STL556685;AKOS005256058;AS-46981;(4-Fluorophenyl)malonic acid diethyl ester;FT-0732140;F11122;A819994;Propanedioic acid, 2-(4-fluorophenyl)-, 1,3-diethyl ester

Chemical Property of Diethyl 2-(4-fluorophenyl)malonate

Chemical Property:

• Vapor Pressure: 0.000961mmHg at 25°C
• Refractive Index: 1.4774 (589.3 nm 20℃)
• Boiling Point: 302.9 °C at 760 mmHg
• PKA: 11.53±0.46(Predicted)
• Flash Point: 132.6 °C
• PSA: 52.60000
• Density: 1.173 g/cm³
• LogP: 2.03550
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 254.09543712
• Heavy Atom Count: 18
• Complexity: 267

Purity/Quality:

99%, ^*data from raw suppliers

Diethyl2-(4-fluorophenyl)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C1=CC=C(C=C1)F)C(=O)OCC

Technology Process of Diethyl 2-(4-fluorophenyl)malonate

There total 8 articles about Diethyl 2-(4-fluorophenyl)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: 87.0%

4-fluoro-1-iodobenzene (352-34-1) + diethyl malonate (105-53-3) → diethyl 2-(4-fluorophenyl)malonate (2965-90-4)

Guidance literature:

With copper; caesium carbonate; In dimethyl sulfoxide; at 70 ℃; for 6h; Inert atmosphere;

DOI:10.1055/s-0033-1338437

Reference yield: 83.0%

tris(4-fluorophenyl)boroxine (448-59-9) + diethyl malonate (105-53-3) → diethyl 2-(4-fluorophenyl)malonate (2965-90-4)

Guidance literature:

With cesium acetate; copper(II) bis(trifluoromethanesulfonate); triethylamine; In 1,2-dichloro-ethane; at 30 ℃; for 44h; Glovebox; Inert atmosphere;

DOI:10.1002/anie.201510558

Reference yield: 80.0%

1-Bromo-4-fluorobenzene (460-00-4) + diethyl malonate (105-53-3) → diethyl 2-(4-fluorophenyl)malonate (2965-90-4)

Guidance literature:

With tri-tert-butyl phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 70 ℃; for 3h;

DOI:10.1021/jo016226h

upstream raw materials:

1-Bromo-4-fluorobenzene

diethyl malonate

ethyl cyanoformate

ethyl 2-(4-fluorophenyl)acetate

Downstream raw materials:

diethyl 3-(4-fluorophenyl)cyclobutane-1,1-dicarboxylate

C₂₉H₁₈F₄N₆O

Refernces

• 1、 Li, Zexian,Shi, Zhuangzhi,Wang, Minyan. "Radical Addition Enables 1,2-Aryl Migration from a Vinyl-Substituted All-Carbon Quaternary Center". supporting information. p. 186 - 190. Retrieved 2020/11/02.
• 2、 Nascimento de Oliveira, Marllon,Arseniyadis, Stellios,Cossy, Janine. "Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids". supporting information. p. 4810 - 4814. Retrieved 2018/03/21.