Diethyl 2-[(4-fluorophenyl)methylene]malonate

Base Information

• Chemical Name: Diethyl 2-[(4-fluorophenyl)methylene]malonate
• CAS No.: 790-53-4
• Molecular Formula: C14H15FO4
• Molecular Weight: 266.269
• DSSTox Substance ID: DTXSID00377567
• Nikkaji Number: J825.913E
• ChEMBL ID: CHEMBL1448533
• Mol file: 790-53-4.mol

Synonyms:790-53-4;diethyl 2-[(4-fluorophenyl)methylene]malonate;diethyl 2-[(4-fluorophenyl)methylidene]propanedioate;Propanedioic acid, [(4-fluorophenyl)methylene]-, diethyl ester;1,3-diethyl 2-[(4-fluorophenyl)methylidene]propanedioate;MLS000326875;SCHEMBL3218584;CHEMBL1448533;DTXSID00377567;MFCD00049276;AKOS003630169;diethyl 2-(4-fluorobenzylidene)malonate;SMR000179483;4-Fluorobenzylidenemalonic acid diethyl ester;10P-119;1,3-diethyl2-[(4-fluorophenyl)methylidene]propanedioate

Chemical Property of Diethyl 2-[(4-fluorophenyl)methylene]malonate

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 266.09543712
• Heavy Atom Count: 19
• Complexity: 323

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=C(C=C1)F)C(=O)OCC

Technology Process of Diethyl 2-[(4-fluorophenyl)methylene]malonate

There total 3 articles about Diethyl 2-[(4-fluorophenyl)methylene]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: 99.0%

4-fluorobenzaldehyde (459-57-4) + diethyl malonate (105-53-3) → diethyl 2-(4-fluorobenzylidene)malonate (790-53-4)

Guidance literature:

With piperidine; acetic acid; In ethanol; at 110 ℃; for 48h;

DOI:10.1055/s-0033-1340468

Reference yield: 92.0%

4-fluorobenzaldehyde (459-57-4) + Diethyl 2-bromomalonate (685-87-0) → diethyl 2-(4-fluorobenzylidene)malonate (790-53-4)

Guidance literature:

With tri-n-butylarsine; at 80 ℃; for 12h;

DOI:10.1016/0022-328X(89)85082-X

Reference yield: 68.0%

para-fluorobenzylamine (140-75-0) + diethyl malonate (105-53-3) → diethyl 2-(4-fluorobenzylidene)malonate (790-53-4)

Guidance literature:

para-fluorobenzylamine; With fluorenone imine; In toluene; at 20 ℃; for 1h;

diethyl malonate; In toluene; for 48h; Reflux; Inert atmosphere;

DOI:10.1039/c9ob02163a

upstream raw materials:

4-fluorobenzaldehyde

diethyl malonate

Diethyl 2-bromomalonate

para-fluorobenzylamine

Downstream raw materials:

2-[(Diethoxy-thiophosphorylsulfanyl)-(4-fluoro-phenyl)-methyl]-malonic acid diethyl ester

diethyl 2-[(diethoxyphosphoryl)(4-fluorophenyl)methyl]malonate

ethyl 3-cyano-3-(4-fluorophenyl)propanoate

Refernces

• 1、 Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.. "Ball-Milling-Enabled Reactivity of Manganese Metal**". supporting information. p. 23128 - 23133. Retrieved 2021/09/20.
• 2、 Banerjee, Prabal,Maajid Taily, Irshad,Saha, Debarshi. "Electricity Driven 1,3-Oxohydroxylation of Donor-Acceptor Cyclopropanes: a Mild and Straightforward Access to β-Hydroxy Ketones". supporting information. p. 5053 - 5057. Retrieved 2021/09/30.