Diethyl 2-(4-chlorobenzylidene)malonate

Base Information

• Chemical Name: Diethyl 2-(4-chlorobenzylidene)malonate
• CAS No.: 6827-40-3
• Molecular Formula: C14H15ClO4
• Molecular Weight: 282.724
• Hs Code.: 2917399090
• NSC Number: 165832
• DSSTox Substance ID: DTXSID00304459
• Nikkaji Number: J324.999I
• Mol file: 6827-40-3.mol

Synonyms:Diethyl 2-(4-chlorobenzylidene)malonate;6827-40-3;diethyl 2-[(4-chlorophenyl)methylidene]propanedioate;NSC165832;diethyl 2-[(4-chlorophenyl)methylene]malonate;SCHEMBL5860473;DTXSID00304459;MVRRBDRVDOIABW-UHFFFAOYSA-N;Diethyl 4-chlorobenzylidenemalonate;MFCD00018786;AKOS005075854;diethyl (4-chlorobenzylidene)-malonate;Diethyl2-(4-chlorobenzylidene)malonate;NSC-165832;CS-0331371;10P-012;Diethyl [(4-chlorophenyl)methylidene]propanedioate;2-(4-chloro-benzylidene)-malonic acid diethyl ester;1,3-diethyl 2-[(4-chlorophenyl)methylidene]propanedioate

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

Chemical Property:

• Vapor Pressure: 4.61E-05mmHg at 25°C
• Boiling Point: 349.7°Cat760mmHg
• Flash Point: 129.7°C
• PSA: 52.60000
• Density: 1.22g/cm³
• LogP: 2.84960
• Storage Temp.: 2-8°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 282.0658866
• Heavy Atom Count: 19
• Complexity: 323

Purity/Quality:

99%min ^*data from raw suppliers

Diethyl 2-(4-chlorobenzylidene)malonate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 10 articles about Diethyl 2-(4-chlorobenzylidene)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: 100.0%

4-chlorobenzaldehyde (104-88-1) + diethyl malonate (105-53-3) → diethyl 4-chlorobenzylidenemalonate (6827-40-3)

Guidance literature:

With C₁₆H₁₄MnN₂O₂⁽¹⁺⁾*[(Si₃Mg_5.5Li_0.3)O₂₀(OH)4]^(1-); In toluene; at 120 ℃; for 72h; Inert atmosphere;

DOI:10.1039/c2cy20442h

Reference yield: 99.0%

diethyl dibromomalonate (631-22-1) + 4-chlorobenzaldehyde (104-88-1) → diethyl 4-chlorobenzylidenemalonate (6827-40-3)

Guidance literature:

With dibutyl telluride; In tetrahydrofuran; at 50 ℃;

DOI:10.1080/00397919108019792

Reference yield: 93.0%

4-chlorobenzaldehyde (104-88-1) + Diethyl 2-bromomalonate (685-87-0) → diethyl 4-chlorobenzylidenemalonate (6827-40-3)

Guidance literature:

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

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

upstream raw materials:

4-chlorobenzaldehyde

diethyl malonate

diethyl dibromomalonate

Diethyl 2-bromomalonate

Downstream raw materials:

<α-(O,O-Diethyl-phosphono)-4-chlor-benzyl>-malonsaeure-diethylester

2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylic acid diethyl ester

diethyl (4-chlorobenzyl)malonate

diethyl bromo[bromo(4-chlorophenyl)methyl]malonate

Refernces

• 1、 Yang, Lu,Zhu, Jiang,Xie, Fukai,Peng, Xiaoshi,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng. "Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins". . p. 1053 - 1060. Retrieved 2019/09/06.
• 2、 Lima, Fabio,Grunenberg, Lars,Rahman, Husaini B. A.,Labes, Ricardo,Sedelmeier, Joerg,Ley, Steven V.. "Organic photocatalysis for the radical couplings of boronic acid derivatives in batch and flow". supporting information. p. 5606 - 5609. Retrieved 2018/06/04.