2-Amino-2-phenylacetic acid

2-Amino-2-phenylacetic acid Basic information
Product Name:2-Amino-2-phenylacetic acid
Synonyms:RARECHEM AK ML 0501;(.+/-.)-alpha-Phenylglycine;(+/-)-benzeneaceticaci;.alpha.-amino-,(+-)-Benzeneaceticacid;-Aminobenzeneaceticacid;Benzeneacetic acid, alpha-amino-, (±;Benzeneaceticacid,-amino-,(+-)-;PHENYLGLYCINE(D,L-)
CAS:2835-06-5
MF:C8H9NO2
MW:151.17
EINECS:220-608-1
Product Categories:Aromatic Building Blocks;GLYCINESCAFFOLD;Pharmaceutical Intermediates;Phenylglycine [Phg]
Mol File:2835-06-5.mol
2-Amino-2-phenylacetic acid Structure
2-Amino-2-phenylacetic acid Chemical Properties
Melting point 290 °C (subl.)(lit.)
alpha [α]D20-0.5~+0.5゜ (c=5, dil. HCl)
Boiling point 273.17°C (rough estimate)
density 1.2023 (rough estimate)
refractive index 1.5810 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility almost transparency in Sodium hydroxide solution
pka1.94±0.10(Predicted)
form Crystalline Powder
color White to off-white
Water Solubility 115g/L(100 ºC)
Merck 14,7291
BRN 3197862
InChIKeyZGUNAGUHMKGQNY-UHFFFAOYSA-N
CAS DataBase Reference2835-06-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetic acid, «alpha»-amino-, (.+/-.)-(2835-06-5)
EPA Substance Registry System2-Phenylglycine (2835-06-5)
Safety Information
Hazard Codes F,C
Risk Statements 11-34
Safety Statements 24/25-45-36/37/39-26-16
WGK Germany 3
TSCA Yes
HS Code 29224999
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2-Amino-2-phenylacetic acid Usage And Synthesis
Description2-Amino-2-phenylacetic acid is a natural compound that has been identified as a selective inhibitor of cyclooxygenase 2 (COX-2), and it exhibits antiinflammatory activity. It has been shown to inhibit COX-2 at low concentrations and to be less potent than aspirin in inhibiting COX-1. It is also an amide, with a molecular weight of 296. In order to determine the structure of it, XRD data was collected from the monosodium salt form of the compound. The ester hydrochloride form was used for enzyme activity assays because it is more soluble in water than the free base form. The synthesis of 2-Amino-2-phenylacetic acid was achieved through a two step process involving amide formation and hydrolysis.
Chemical Propertieswhite amorphous powder
UsesDL-α-Phenylglycine is used as a reagent in the synthesis of benzoquinone-amino acid conjugates which have antibacterial activity.
DefinitionChEBI: An amino acid with a structure in which a phenyl ring is bonded to the alpha-carbon of glycine.
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 3, p. 84, 1955
Synthetic Communications, 2, p. 423, 1972 DOI: 10.1080/00397917208081791
2-AMINOPHENYLACETIC ACID 3-Aminophenylacetic acid Sulfanilic acid (2S)-2-Amino-2-phenylacetic acid DL-Phenylalanine ALTRENOGEST 4-Aminobenzoic acid Triphenyltin acetate o-Aminophenylacetic acid Sulfanilamide 4-Aminophenylacetic acid p-Anisidine Aniline 2-AMINOPHENYLACETIC ACID 4-Hydroxy-D-(-)-2-phenylglycine AMINO ACIDS Anthranilic acid Diethylstilbestrol

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