Diethyl benzylidenemalonate

Base Information

• Chemical Name: Diethyl benzylidenemalonate
• CAS No.: 5292-53-5
• Molecular Formula: C14H16 O4
• Molecular Weight: 248.279
• Hs Code.: 2917399090
• European Community (EC) Number: 226-137-8
• NSC Number: 1272
• UNII: T3XFN6T8WY
• DSSTox Substance ID: DTXSID30200975
• Nikkaji Number: J8.833A
• ChEMBL ID: CHEMBL1496422
• Mol file: 5292-53-5.mol

Synonyms:Diethyl benzylidenemalonate;5292-53-5;Diethyl benzalmalonate;Diethyl 2-benzylidenemalonate;Ethyl benzylidenemalonate;Diethyl (phenylmethylene)malonate;diethyl 2-benzylidenepropanedioate;Diethylbenzylidenemalonate;2-Benzylidene-malonic acid diethyl ester;Propanedioic acid, (phenylmethylene)-, diethyl ester;Malonic acid, benzylidene-, diethyl ester;Benzylidenemalonic acid diethyl ester;1,3-diethyl 2-(phenylmethylidene)propanedioate;AI3-02423;Benzalmalonic Acid Diethyl Ester;NSC-1272;EINECS 226-137-8;MFCD00009149;EC 226-137-8;T3XFN6T8WY;SCHEMBL935186;diethyl benzylidenepropanedioate;Diethyl 2-benzylidenemalonate #;CHEMBL1496422;2-Benzylidenemalonic acid diethyl;DTXSID30200975;NSC1272;Benzal-Malonic Acid Diethyl Ester;NSC 1272;.beta.,.beta.-Diethoxycarbonylstyrene;benzylidenemalonic acid, diethyl ester;AKOS002133974;NCGC00166046-01;NCGC00166046-02;2-benzylidene-propanedioic acid diethyl ester;A7717;B0420;FT-0622850;2-(1-(2-ethylphenyl)propylidene)malonic acid;Diethyl benzylidenemalonate, >=99.0% (GC);D88642;EN300-129393;AB01334643-02;Propanedioic acid, 2-(phenylmethylene)-, diethyl ester

Chemical Property of Diethyl benzylidenemalonate

Chemical Property:

• Vapor Pressure: 0.00012mmHg at 25°C
• Melting Point: 28-31°C
• Refractive Index: n20/D 1.536(lit.)
• Boiling Point: 215-217 °C30 mm Hg(lit.)
• Flash Point: 149.6°C
• PSA: 52.60000
• Density: 1.129g/cm³
• LogP: 2.19620
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 248.10485899
• Heavy Atom Count: 18
• Complexity: 294

Purity/Quality:

99.9% ^*data from raw suppliers

1,3-Diethyl2-(phenylmethylidene)propanedioate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=CC=C1)C(=O)OCC
• Uses: Diethyl benzylidenemalonate is used as a pharmaceutical intermediate. It is also involved in the Conjugate addition of cyanide ion to arylidenemalonic esters provides a useful route to arylsuccinic acids.

Technology Process of Diethyl benzylidenemalonate

There total 72 articles about Diethyl benzylidenemalonate 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: 96.0%

benzaldehyde dimethyl acetal (1125-88-8) + diethyl malonate (105-53-3) → diethyl benzalmalonate (5292-53-5)

Guidance literature:

With DMAN-SO₃H-SiO₂-5-5; In water; for 24h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c3cy00269a

Reference yield: 93.0%

diethyl dibromomalonate (631-22-1) + benzaldehyde (100-52-7) → diethyl benzalmalonate (5292-53-5)

Guidance literature:

With dibutyl telluride; In tetrahydrofuran; at 50 ℃; Mechanism; other carbonyl compounds;

DOI:10.1080/00397919108019792

Reference yield: 92.0%

diethyl malonate (105-53-3) + benzyl alcohol (100-51-6,185532-71-2) → benzaldehyde (100-52-7) + diethyl benzalmalonate (5292-53-5)

Guidance literature:

With dihydrogen peroxide; In water; acetonitrile; at 80 ℃; for 16h; Catalytic behavior;

DOI:10.1002/cctc.201501365

upstream raw materials:

piperidine

benzaldehyde

diethyl malonate

benzylidene dichloride

Downstream raw materials:

(α-piperidino-benzyl)-malonic acid diethyl ester

1-Hydroxy-2-(hydroxy-diphenyl-methyl)-1.3-diphenyl-indan

N'-benzylidene-N,N-dimethyl-p-phenylenediamine

(3-oxo-1,2,3-triphenyl-propyl)-malonic acid diethyl ester

Refernces

• 1、 Sugino, Kotaro,Oya, Nobuhiro,Yoshie, Naoko,Ogura, Masaru. "A simple modification creates a great difference: New solid-base catalyst using methylated N-substituted SBA-15". . p. 20030 - 20032. Retrieved 2011.
• 2、 Climent, Maria J.,Corma, Avelino,Dominguez, Irene,Iborra, Sara,Sabater, Maria J.,Sastre, German. "Gem-diamines as highly active organocatalysts for carbon-carbon bond formation". . p. 136 - 146. Retrieved 2007.
• 3、 Chen, Xinqing,Arruebo, Manuel,Yeung, King Lun. "Flow-synthesis of mesoporous silicas and their use in the preparation of magnetic catalysts for Knoevenagel condensation reactions". . p. 140 - 147. Retrieved 2013.
• 4、 Llopis, Sebastián,Velty, Alexandra,Díaz, Urbano. "Active Base Hybrid Organosilica Materials based on Pyrrolidine Builder Units for Fine Chemicals Production". . p. 5012 - 5024. Retrieved 2021/10/19.
• 5、 Ramaiah, Manjunatha M.,Shivananju, Nanjunda Swamy,Shubha, Priya Babu. "A facile, efficient and solvent-free titanium (IV) ethoxide catalysed knoevenagel condensation of aldehydes and active methylenes". . p. 107 - 115. Retrieved 2020/02/04.