(S)-(+)-2-Phenylglycinol
[CAS# 20989-17-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: (S)-(+)-2-Phenylglycinol
• Synonyms: (S)-(+)-2-Amino-2-phenylethanol; L(+)-alpha-Phenylglycinol; L-beta-Aminophenethyl alcohol
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Protein Sequence: X
• CAS Registry Number: 20989-17-7
• EC Number: 606-683-7
• SMILES: C1=CC=C(C=C1)[C@@H](CO)N

Properties

• Melting point: 75-78 °C (Expl.)
• Alpha: +33°, c = 0.75 (1 M HCl) (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

(S)-(+)-2-Phenylglycinol is a chiral organic compound classified as an amino alcohol, specifically an α-amino-β-phenylethanol. Its molecular structure consists of a primary amine group (–NH₂) and a primary alcohol group (–CH₂OH) attached to a central carbon that also bears a phenyl substituent. The compound is optically active, and the (S)-(+)-enantiomer refers to the stereoisomer that rotates plane-polarized light in a dextrorotatory direction and has an absolute configuration corresponding to the (S)-form according to the Cahn–Ingold–Prelog priority rules.

The discovery and synthetic development of (S)-(+)-2-phenylglycinol emerged from the broader study of amino alcohols in organic and pharmaceutical chemistry. Chiral amino alcohols are valuable as building blocks and auxiliaries in asymmetric synthesis. The compound's configuration and functional groups make it highly versatile for a variety of synthetic transformations, and it has been widely used as a chiral precursor, resolving agent, and ligand in catalytic asymmetric reactions.

One of the principal applications of (S)-(+)-2-phenylglycinol is in the synthesis of chiral pharmaceuticals and natural product analogs. It has been used in the construction of β-amino alcohol-containing drugs and in the asymmetric synthesis of β-lactams, epoxides, and aziridines. The chiral center adjacent to both nucleophilic (NH₂) and electrophilic (OH) groups facilitates regioselective and stereoselective reactions.

References

2021. One-pot synthesis of (R)- and (S)-phenylglycinol from bio-based l-phenylalanine by an artificial biocatalytic cascade. Bioresources and Bioprocessing, 8(1).
DOI: 10.1186/s40643-021-00448-5

2020. Synthesis of functionalized oxazolidines by multicomponent reactions of 1,2-amino alcohols (microreview). Chemistry of Heterocyclic Compounds, 56(4).
DOI: 10.1007/s10593-020-02681-w

2019. Synthesis of novel α-aminophosphonates under microwave irradiation, biological evaluation as antiproliferative agents and apoptosis inducers. Medicinal Chemistry Research, 28(10).
DOI: 10.1007/s00044-019-02436-z