Phenylmalonic acid

Base Information

• Chemical Name: Phenylmalonic acid
• CAS No.: 2613-89-0
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• Hs Code.: 2917399090
• European Community (EC) Number: 220-044-6
• NSC Number: 41697,27164
• UNII: 92EX195E1G
• DSSTox Substance ID: DTXSID5062552
• Nikkaji Number: J153H
• Wikidata: Q27094928
• Metabolomics Workbench ID: 148554
• ChEMBL ID: CHEMBL78794
• Mol file: 2613-89-0.mol

Synonyms:phenylmalonic acid

Chemical Property of Phenylmalonic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 6.63E-06mmHg at 25°C
• Melting Point: 149-152 °C (dec.)(lit.)
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 363 °C at 760 mmHg
• PKA: pK1:2.58;pK2:5.03 (25°C)
• Flash Point: 187.5 °C
• PSA: 74.60000
• Density: 1.399 g/cm³
• LogP: 0.93940
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 180.04225873
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

98% ^*data from raw suppliers

Phenylmalonic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)C(=O)O
• Uses: Phenylmalonic Acid is used as the starting material in the synthesis of Sodium Indanylcarbinicillin (S635000); a compound which has been shown to reduce blood pressure in mammals and also has been used as a β-lactam antibiotic.

Technology Process of Phenylmalonic acid

There total 26 articles about Phenylmalonic 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: 91.0%

diethyl 2-phenylmalonate (83-13-6) → phenylmalonic acid (2613-89-0)

Guidance literature:

With water; sodium hydroxide; at 60 ℃; for 3h;

Reference yield: 28.0%

benzylidene dichloride (98-87-3) + carbon dioxide (124-38-9,18923-20-1) → phenylacetic acid (103-82-2) + Chloro-phenyl-acetic acid (4755-72-0,39266-56-3) + phenylmalonic acid (2613-89-0)

Guidance literature:

With Al(III) salt; tetrabutylammomium bromide; In N,N-dimethyl-formamide; under 18240 Torr; anode = Al 99.9percent ; cathode = Zn 99percent ; cathodic current density 100 A m_-2;

DOI:10.1016/S0040-4039(01)81424-6

Reference yield:

toluene (108-88-3,15644-74-3,16713-13-6) → phenylacetic acid (103-82-2) + phenylmalonic acid (2613-89-0)

Guidance literature:

With 1-Chloropentane; sodium; Petroleum ether; Einleiten von Kohlendioxid in das Reaktionsgemisch;

DOI:10.1021/ja01303a063

upstream raw materials:

phenylacetic acid

dimethyl 2-phenylmalonate

diethyl 2-phenylmalonate

toluene

Downstream raw materials:

dimethyl 2-phenylmalonate

3-amino-2-phenyl-propionic acid

1,3-dimethyl-5-phenyl-pyrimidine-2,4,6(1H,3H,5H)-trione

phenylacetic acid

Refernces

Anti-mycobacterial 4-hydroxy-3-phenylpyridin-2(1H)-ones

10.1016/0223-5234(91)90194-R

The research investigates the synthesis and anti-mycobacterial activity of 4-hydroxy-3-phenylpyridin-2(1H)-ones with various substituents. The purpose is to explore the potential of these compounds as inhibitors of Mycobacterium tuberculosis. The study synthesizes these compounds by reacting ethyl p-aminocrotonates with dialkyl malonates or "magic malonates" (2,4,6-trichlorophenyl malonates). Key chemicals used include ethyl p-aminocrotonates, phenylmalonates, and various substituted malonates. The synthesized compounds were tested against M. tuberculosis H37Ra, Escherichia coli B, and Staphylococcus aureus ATCC 25923. The results showed significant inhibitory effects on M. tuberculosis, with some compounds achieving minimal inhibitory concentrations (MIC) as low as 8 μg/ml. The study concludes that the presence of a phenyl group para to the nitrogen atom and an unoccupied β-position in the heterocycle are essential for anti-mycobacterial activity. Substituents at the nitrogen atom and the phenyl ring modulate the activity, with N-substituents like pentyl and hexyl showing enhanced activity. The findings suggest that these pyridin-2(1H)-ones could serve as promising candidates for developing new anti-tuberculosis agents.

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