(3R)-3-Amino-1-butanol
[CAS# 61477-40-5]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Amino alcohol derivative
• Name: (3R)-3-Amino-1-butanol
• Synonyms: (R)-3-Aminobutan-1-ol; (R)-3-Aminobutanol
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• Protein Sequence: X
• CAS Registry Number: 61477-40-5
• EC Number: 640-387-9
• SMILES: C[C@H](CCO)N

Properties

• Density: 0.927
• Boiling point: 168 °C
• Flash point: 56 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H314-H318-H412
• Safety Statements: P260-P264-P264+P265-P270-P273-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Flammable liquids	Flam. Liq.	3	H226
Acute hazardous to the aquatic environment	Aquatic Acute	3	H402

Discovery and Applications

(3R)-3-Amino-1-butanol, also known as L-threoninol or L-3-amino-1-butanol, was first synthesized and characterized through organic chemistry research aimed at developing amino alcohols with specific stereochemistry. Chemists focused on modifying the structure of butanol—a four-carbon alcohol—to introduce an amino group at the third carbon position while preserving the stereochemistry essential for biological activity. Through synthetic routes involving the reduction of suitable ketones or the amino acid threonine, (3R)-3-Amino-1-butanol was successfully produced. Its discovery represented a significant advancement in organic chemistry, providing a versatile building block for the synthesis of various organic compounds with pharmacological, industrial, and research applications.

(3R)-3-Amino-1-butanol serves as a key intermediate in the synthesis of pharmaceutical compounds, including chiral building blocks, amino acids, and peptide derivatives. Its stereochemistry and amino functionality enable the construction of complex molecules with precise spatial arrangements, crucial for biological activity and pharmacological effects. Researchers explore (3R)-3-Amino-1-butanol derivatives as potential drug candidates for various therapeutic areas, including cardiovascular diseases, central nervous system disorders, and infectious diseases. These compounds exhibit diverse pharmacological activities, such as enzyme inhibition, receptor modulation, or antimicrobial action, making them promising candidates for drug development.

(3R)-3-Amino-1-butanol derivatives are used as chiral auxiliaries in asymmetric synthesis to control the stereochemistry of reactions and enhance the selectivity of chemical transformations. They facilitate the synthesis of chiral agrochemicals, including insecticides, herbicides, and fungicides, with improved efficacy and environmental compatibility. Some derivatives of (3R)-3-Amino-1-butanol exhibit plant growth-regulating properties, influencing various physiological processes in plants, such as root development, flowering, and fruit ripening. These compounds are employed in agriculture to improve crop yield, quality, and resistance to environmental stressors, contributing to sustainable agriculture practices.

(3R)-3-Amino-1-butanol derivatives are used as additives in polymer synthesis to modify the properties of polymers, such as flexibility, adhesion, and thermal stability. They serve as chain extenders, crosslinking agents, or stabilizers, enhancing the performance of polymers in various applications, including coatings, adhesives, and elastomers. Some derivatives of (3R)-3-Amino-1-butanol are employed in surface modification techniques to functionalize materials, such as nanoparticles, membranes, and surfaces of biomedical implants. These compounds facilitate the attachment of functional groups or biomolecules, enabling tailored surface properties for specific applications in biotechnology, catalysis, and medical devices.

References

2024. Synthesis and Antitumor Activity of Dolutegravir Derivatives Bearing 1,2,3-Triazole Moieties. *BMC Chemistry*, 18(1). DOI: 10.1186/s13065-024-01205-3

2020. Reshaping the Substrate Binding Region of (R)-Selective ω-Transaminase for Asymmetric Synthesis of (R)-3-Amino-1-Butanol. *Applied Microbiology and Biotechnology*, 104(9). DOI: 10.1007/s00253-020-10539-6

2016. Development of Synthetic Routes to Dolutegravir. *Synthesis of Heterocycles in Contemporary Medicinal Chemistry*. DOI: 10.1007/7081_2016_200