2-Amino-2-phenylacetic acid

Synonym(s):(±)-α-Aminophenylacetic acid;DL-α-Phenylglycine

CAS NO.：2835-06-5
Empirical Formula: C8H9NO2
Molecular Weight: 151.17
MDL number: MFCD00064402
EINECS: 220-608-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-08 20:21:46

What is 2-Amino-2-phenylacetic acid?

Description

2-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 properties

white amorphous powder

The Uses of 2-Amino-2-phenylacetic acid

DL-α-Phenylglycine is used as a reagent in the synthesis of benzoquinone-amino acid conjugates which have antibacterial activity.

Definition

ChEBI: 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

Properties of 2-Amino-2-phenylacetic acid

Melting point:	290 °C (subl.)(lit.)
Boiling point:	273.17°C (rough estimate)
alpha	[α]D20-0.5～+0.5゜ (c=5, dil. HCl)
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
form	Crystalline Powder
pka	1.94±0.10(Predicted)
color	White to off-white
Water Solubility	115g/L(100 ºC)
Merck	14,7291
BRN	3197862
CAS DataBase Reference	2835-06-5(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetic acid, «alpha»-amino-, (.+/-.)-(2835-06-5)
EPA Substance Registry System	2-Phenylglycine (2835-06-5)

Safety information for 2-Amino-2-phenylacetic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.