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Phenylacetic Acid

Base Information Edit
  • Chemical Name:Phenylacetic Acid
  • CAS No.:103-82-2
  • Molecular Formula:C8H8O2
  • Molecular Weight:136.15
  • Hs Code.:2916.33
  • European Community (EC) Number:203-148-6
  • ICSC Number:1260
  • NSC Number:139637,125718
  • UNII:ER5I1W795A
  • DSSTox Substance ID:DTXSID2021656
  • Nikkaji Number:J10.117F
  • Wikipedia:Phenylacetic_acid
  • Wikidata:Q410842
  • NCI Thesaurus Code:C77487
  • RXCUI:33332
  • Metabolomics Workbench ID:37136
  • ChEMBL ID:CHEMBL1044
  • Mol file:103-82-2.mol
Phenylacetic Acid

Synonyms:phenylacetate;phenylacetic acid;phenylacetic acid, ammonium salt;phenylacetic acid, calcium salt;phenylacetic acid, cesium salt;phenylacetic acid, lithium salt;phenylacetic acid, mercury salt;phenylacetic acid, potassium salt;phenylacetic acid, rubidium salt;phenylacetic acid, sodium salt;phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd;sodium phenylacetate

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Phenylacetic Acid Edit
Chemical Property:
  • Appearance/Colour:White crystals with a honey-like odour 
  • Vapor Pressure:1 mm Hg ( 97 °C) 
  • Melting Point:76-78 °C(lit.) 
  • Refractive Index:1.552 
  • Boiling Point:265.499 °C at 760 mmHg 
  • PKA:4.28(at 18℃) 
  • Flash Point:156.213 °C 
  • PSA:37.30000 
  • Density:1.165 g/cm3 
  • LogP:1.31370 
  • Storage Temp.:Store at RT. 
  • Water Solubility.:15 g/L (20 ºC) 
  • XLogP3:1.4
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:2
  • Exact Mass:136.052429494
  • Heavy Atom Count:10
  • Complexity:114
Purity/Quality:
Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38 
  • Safety Statements: 26-36-37/39 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Other Classes -> Organic Acids
  • Canonical SMILES:C1=CC=C(C=C1)CC(=O)O
  • Recent ClinicalTrials:Phenylacetate in Treating Children With Recurrent or Progressive Brain Tumors
  • Inhalation Risk:A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
  • Effects of Short Term Exposure:The substance is irritating to the eyes. The substance is mildly irritating to the skin.
  • General Description Phenylacetic acid is a versatile organic compound with applications in various chemical syntheses and pharmaceutical research. It serves as a key reactant in nucleophilic addition reactions with epoxides to form γ-lactones or hydroxy acids, demonstrating improved yields and selectivity under optimized conditions involving lithium chloride. In anti-malarial drug development, phenylacetic acid derivatives, particularly those para-substituted with methyl or trifluoromethyl groups, exhibit potent activity against Plasmodium falciparum. Additionally, phenylacetic acid derivatives are utilized in the synthesis of benzofuran- and indol-2-yl-methanamine derivatives, highlighting their role in producing biologically active compounds. Mass spectrometric studies further reveal unique fragmentation behaviors of ortho-substituted phenylacetamides, emphasizing the influence of substituents on their ionization and decomposition patterns.
Technology Process of Phenylacetic Acid

There total 937 articles about Phenylacetic 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:
Guidance literature:
With manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;
DOI:10.1002/chem.201202640
Guidance literature:
With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;
DOI:10.1002/chem.201202640
Guidance literature:
With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Solvent; Reagent/catalyst; Inert atmosphere;
DOI:10.1002/chem.201202640
Refernces Edit

Efficient addition of acid enediolates to epoxides

10.1002/ejoc.200300795

The research focuses on the development of efficient conditions for the addition of acid enediolates to epoxides, offering an alternative to the traditional use of aluminum enolates. The study introduces a method that employs a sub-stoichiometric amount of amine for dianion generation and the activation of epoxides with lithium chloride (LiCl). The reactants used in the experiments include various epoxides and phenylacetic acid, which are subjected to nucleophilic addition reactions under these new conditions. The experiments are designed to optimize factors such as the amount and nature of the lithium amide used as a base, temperature, and reaction time. Analyses utilized to evaluate the outcomes encompass techniques like infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. The results indicated improved yields and selectivity in the formation of ?-lactones or hydroxy acids, which could be further converted to ?-lactones upon refluxing in toluene. The study also explored the impact of different Lewis acids and additives on the reaction's diastereoselectivity and regioselectivity, with LiCl showing the most promising results, particularly when used in inverse addition.

Structure-activity relationships of novel anti-malarial agents: Part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides

10.1016/S0960-894X(02)01003-X

The study focuses on the structure-activity relationships of novel anti-malarial agents, specifically N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2furyl]acrylic acid amides. The researchers developed a lead compound, benzophenone 4g, which was modified by replacing the tolylacetyl residue at the 2-amino group with various acyl residues to determine their influence on anti-malarial activity. The chemicals used included 2-amino-5-nitrobenzophenone, acid chlorides for acylation, SnCl2?2H2O for reduction, and 3-[5-(4-nitrophenyl)-2-furyl]acrylic acid chloride for further acylation. The purpose of these chemicals was to synthesize and test a series of compounds to identify the optimal acyl residue structure for high anti-malarial activity, with the aim of overcoming drug resistance in Plasmodium falciparum, the causative agent of malaria. The study found that a phenylacetic acid substructure substituted in its para-position with methyl or similar-sized substituents was essential for high activity, with the trifluoromethyl-substituted derivative showing the most potent activity.

Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives

10.1016/j.tetlet.2014.11.015

The study presents a novel synthetic method for the production of benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives, which are significant in synthetic strategies due to their presence in biologically active compounds. The synthesis involves the use of ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting materials, respectively. Key intermediates in this process are compounds bearing the oxazole-4-carboxylic acid methylester moiety. The study details the synthesis process, which includes the use of reagents such as HBr/HAc for the production of benzofuran-2-yl-methanamines and HCl for the synthesis of indol-2-yl-methanamines after the reduction of the nitro-group. The method is effective with electron-donating substituents but has limitations with electron-withdrawing substituents. The study also discusses the availability and preparation of the starting phenylacetic acids and explores the synthetic procedure's applicability to a variety of substituted phenylacetic acids, demonstrating its potential as a general synthetic method for these compounds.

MS investigations on derivatives of phenylacetic acid, I: Loss of ortho-substituents from Ionized phenylacetamides

10.1002/ardp.19883210506

The research focuses on mass spectrometric investigations of derivatives of phenylacetic acid, specifically examining the loss of ortho-substituents from ionized phenylacetamides. The purpose of this study was to explore the mass spectrometry (MS) behavior of ortho-substituted phenylacetamides, particularly the loss of substituents such as chlorine, bromine, and nitro groups, which result in strong (M-X)+ signals in their 70 and 12 eV mass spectra. The research concluded that the loss of ortho-substituents is position-specific, with additional methoxy substitution facilitating the loss of the ortho-nitro group. The study also discussed the MI- and CAD-spectra of the (M-X')+-ions and proposed that a special ortho-effect might be at play, where the ortho-substituent is replaced by an intramolecular attack of the amide group. Various phenylacetamides, including 2a-h, 3a-g, 4a, b, 5a, b, and others, were synthesized from corresponding phenylacetic acids using SOCl2 and then with aqueous ammonia or dimethylamine. The chemicals used in the process encompassed a range of phenylacetamides with different substituents, such as H, CH3, F, Cl, Br, NO2, and OCH3, among others, to investigate their specific mass spectrometry patterns and fragmentation behaviors.