L-Phenylglycinol
[CAS# 3182-95-4]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: L-Phenylglycinol
• Synonyms: L(-)-2-Amino-3-phenyl-1-propanol; L-2-amino-3-phenylpropan-1-ol; (S)-2-Amino-3-phenyl-1-propanol; (S)-(-)-2-Amino-3-phenyl-1-propanol; L-(-)-Phenylalaninol
• Protein Sequence: F
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.21
• CAS Registry Number: 3182-95-4
• EC Number: 221-674-4
• SMILES: C1=CC=C(C=C1)C[C@@H](CO)N

Properties

• Melting point: 92-94 ºC
• alpha: -23 º (c=5,EtOH)

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovory and Applicatios

L-Phenylglycinol, a chiral amino alcohol with the formula C8H11NO, was first synthesized and studied in the early 20th century. It is derived from phenylglycine and serves as a crucial intermediate in organic synthesis. The discovery of L-Phenylglycinol provided chemists with an important tool for stereoselective synthesis, enabling the creation of compounds with specific chiral configurations. Its synthesis typically involves the reduction of phenylglycine derivatives or via asymmetric synthesis techniques.

L-Phenylglycinol is extensively used in the pharmaceutical industry as a chiral building block and resolving agent. Its ability to induce chirality in drug molecules makes it essential for the synthesis of enantiomerically pure pharmaceuticals. L-Phenylglycinol is employed in the synthesis of various active pharmaceutical ingredients (APIs), including antihypertensive agents, antibiotics, and antiviral drugs.

In the agrochemical sector, L-Phenylglycinol is used to synthesize chiral pesticides and herbicides. These compounds often require specific stereochemistry to effectively target pests or weeds while minimizing environmental impact. L-Phenylglycinol enables the production of agrochemicals with precise biological activities, enhancing their effectiveness and reducing side effects.

L-Phenylglycinol serves as a valuable intermediate in organic synthesis, particularly in asymmetric synthesis and catalysis. Its chiral nature allows it to be used as a ligand in catalytic reactions, facilitating the production of enantioselective compounds. It is also employed in the synthesis of chiral auxiliaries, which are used to control the stereochemistry of subsequent reactions.

In materials science, L-Phenylglycinol is used to develop chiral materials and polymers. These materials have applications in areas such as optical devices, enantioselective sensors, and drug delivery systems. The incorporation of L-Phenylglycinol into polymer chains can impart chirality, leading to materials with unique properties. For example, chiral polymers can exhibit selective binding to specific enantiomers, making them useful in enantioselective separation processes.

L-Phenylglycinol is widely utilized in academic and industrial research to explore new synthetic methodologies and reaction mechanisms. Researchers use it as a model compound to study chiral induction and enantioselective reactions.

Beyond its role in synthesis, L-Phenylglycinol finds applications in various industrial processes. Its use as a chiral auxiliary and ligand in catalytic reactions helps streamline production processes and improve the efficiency of chemical manufacturing.

References

2024. Chiral ferrocenylimine alcohols and corresponding reduced ferrocenyl secondary amine alcohols: synthesis, X-crystal structures and characterization. Transition Metal Chemistry, 49(6).
DOI: 10.1007/s11243-024-00604-8

2023. β-Lactam TRPM8 Antagonists Derived from Phe-Phenylalaninol Conjugates: Structure-Activity Relationships and Antiallodynic Activity. International Journal of Molecular Sciences, 24(19).
DOI: 10.3390/ijms241914894

2021. Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin. ELECTROPHORESIS, 42(21).
DOI: 10.1002/elps.202100076