2-(2-Hydroxyphenyl)glycine

2-(2-Hydroxyphenyl)glycine - Names and Identifiers

Name	amino(2-hydroxyphenyl)acetic acid
Synonyms	Hydroxyphenyl glycine 2-HYDROXY PHENYL GLYCINE 2-(2-Hydroxyphenyl)glycine amino(2-hydroxyphenyl)acetic acid Amino(2-hydroxyphenyl)acetic acid 2-Amino(2-hydroxyphenyl)acetic acid AMINO-(2-HYDROXY-PHENYL)-ACETIC ACID 2-amino-2-(2-hydroxyphenyl)acetic acid Benzeneacetic acid, a-amino-2-hydroxy- Benzeneacetic acid, α-amino-2-hydroxy- 2-AMINO-2-(2-HYDROXYPHENYL)ACETIC ACID benzeneacetic acid, alpha-amino-2-hydroxy- (S)-methyl 2-(2-chlorophenyl)-2-(2-(hydroxymethyl)-6,7- dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetate
CAS	25178-38-5
InChI	InChI=1/C8H9NO3/c9-7(8(11)12)5-3-1-2-4-6(5)10/h1-4,7,10H,9H2,(H,11,12)

2-(2-Hydroxyphenyl)glycine - Physico-chemical Properties

Molecular Formula	C8H9NO3
Molar Mass	167.16
Density	1.396±0.06 g/cm3(Predicted)
Boling Point	358.8±32.0 °C(Predicted)
Flash Point	170.781°C
Vapor Presure	0mmHg at 25°C
pKa	1.82±0.10(Predicted)
Storage Condition	Inert atmosphere,Room Temperature
Refractive Index	1.633

2-(2-Hydroxyphenyl)glycine - Risk and Safety

Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.

2-(2-Hydroxyphenyl)glycine - Reference Information

use

2-hydroxyphenylglycine can be used as an intermediate in pharmaceutical synthesis.

Preparation

a) Dissolve salicylaldehyde and benzamine (molar ratio 1:1) in ethanol, and reflux the mixture for 2 hours. The reaction was stirred at room temperature for another 2 hours, and the solvent was removed under reduced pressure to obtain the imine in a quantitative yield.
B) Add anhydrous tetrahydrofuran (THF) to the obtained imine, slowly add trimethylcyanosilane (TMSCN) dropwise, and the molar amine: TMSCN is 1:3. The reaction mixture is stirred at room temperature for 40 hours, added into the solution of saturated ammonium chloride (NH4Cl), extracted with ether, the ether phase is washed with water, and finally dried with magnesium sulfate, the solvent is removed under vacuum, and α-aminonitrile is quantitatively obtained in the form of oil.
c) The obtained α-aminonitrile is heated in concentrated hydrochloric acid at 60-70 ℃ for 3 hours. Thereafter, the crude oil is allowed to cool and dried under reduced pressure. After drying, the residue was suspended in acetone, filtered and dried to give N-benzyl-2-hydroxyphenylglycine hydrochloride, which was a powdered solid with 97% yield.
d) A solution of hydrochloric acid in Pd(c) is added to a methanol solution (15% by weight of the mass of the substrate)-benzyl-2-hydroxyphenylglycine N, and then hydrogen pressure (50psi) is carried out for 16 hours. The crude product was filtered and the solvent was removed under reduced pressure to obtain 2-hydroxyphenylglycine with 96% yields.

Last Update：2024-04-09 21:54:55