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%,99%, ^*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

• 1、 Capaccio, Vito,Sicignano, Marina,Rodríguez, Ricardo I.,Della Sala, Giorgio,Alemán, José. "Asymmetric Synthesis of α-Trifluoromethylthio-β-Amino Acids under Phase Transfer Catalysis". supporting information. p. 219 - 223. Retrieved 2019/12/30.
• 2、 -. "Mesoionic insecticide". Paragraph 0173-0175. . Retrieved 2020/09/16.