Benzylidenemalonic acid

Base Information

• Chemical Name: Benzylidenemalonic acid
• CAS No.: 584-45-2
• Molecular Formula: C10H8 O4
• Molecular Weight: 192.171
• European Community (EC) Number: 209-538-2
• NSC Number: 28955
• DSSTox Substance ID: DTXSID80207111
• Nikkaji Number: J95.737B
• ChEMBL ID: CHEMBL2148183
• Mol file: 584-45-2.mol

Synonyms:Benzylidenemalonic acid;Benzalmalonic acid;Malonic acid, benzylidene-;584-45-2;2-benzylidenepropanedioic acid;Propanedioic acid, (phenylmethylene)-;EINECS 209-538-2;BRN 2048635;CHEMBL2148183;2-(phenylmethylidene)propanedioic acid;4-09-00-03460 (Beilstein Handbook Reference);2-Benzylidenemalonic acid;benzalmalonsaure;2-Benzylidenemalonic acid #;SCHEMBL39098;DTXSID80207111;NSC28955;BDBM50391684;NSC 28955;NSC-28955;AKOS006272459;AS-0259;LS-88789

Chemical Property of Benzylidenemalonic acid

Chemical Property:

• Vapor Pressure: 1.4E-06mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Boiling Point: 384°C at 760 mmHg
• Flash Point: 200.2°C
• PSA: 74.60000
• Density: 1.413g/cm³
• LogP: 1.23920
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 192.04225873
• Heavy Atom Count: 14
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C(=O)O)C(=O)O

Technology Process of Benzylidenemalonic acid

There total 36 articles about Benzylidenemalonic acid 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: 98.0%

malonic acid (141-82-2) + benzaldehyde (100-52-7) → 2-benzylidenemalonic acid (584-45-2)

Guidance literature:

With nickel; In ethanol; at 25 ℃; for 0.3h; under 760.051 Torr; chemoselective reaction;

DOI:10.1016/j.catcom.2010.01.017

Reference yield: 85.0%

dicobalt octacarbonyl (15226-74-1,61091-28-9,61117-58-6) + (E)-2-chloro-3-phenylacrylic acid (705-55-5) → 2-benzylidenemalonic acid (584-45-2)

Guidance literature:

With calcium hydroxide; carbon monoxide; methyl iodide; In 1,4-dioxane; water; 20°C, 20 h.;

Reference yield: 79.0%

malonic acid (141-82-2) + benzaldehyde (100-52-7) → (E)-3-phenylacrylic acid (140-10-3) + 2-benzylidenemalonic acid (584-45-2)

Guidance literature:

With bentonite; for 0.0833333h; Further Variations:; Reagents; Product distribution; Microwave irradiation;

DOI:10.1039/b009803p

upstream raw materials:

ethanol

malonic acid

benzylidene 1,1-diacetate

benzaldehyde

Downstream raw materials:

Cinnamic acid

(E)-3-phenylacrylic acid

3-Amino-3-phenylpropionic acid

diethyl benzalmalonate

Refernces

Intramolecular cycloaddition of N-phthalimidoaziridines to double and triple carbon-carbon bonds

10.1016/j.tetlet.2009.08.015

The research investigates the intramolecular cycloaddition of N-phthalimidoaziridines to carbon–carbon double and triple bonds. The purpose is to explore the potential of this reaction to produce complex nitrogen-containing heterocyclic compounds, which have applications in various fields including natural product synthesis and pharmaceuticals. The study synthesized N-phthalimidoaziridines with unsaturated side chains from salicylic aldehyde and used oxidative aminoaziridination procedures. Key chemicals involved include salicylic aldehyde, ortho-(allyloxy)- and ortho-(propargyloxy)cinnamic acids, benzylidenemalonic acid derivatives, and N-aminophthalimide. The results showed that thermolysis of these aziridines led to the formation of condensed N-phthalimidopyrrolidines, N-phthalimidopyrrolines, or their subsequent transformations, with yields and product configurations influenced by the nature of the substituents and the type of unsaturated bond. The study concludes that the reaction is a general process for the described compounds, with the rate-determining step likely being the cleavage of the aziridine to form the azomethine ylide. The configuration of the products aligns with a mechanism involving thermally allowed conrotatory ring-opening followed by a concerted 1,3-dipolar cycloaddition.

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