4-Amino-2-methyl-1-butanol
[CAS# 44565-27-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 4-Amino-2-methyl-1-butanol
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16
• CAS Registry Number: 44565-27-7
• EC Number: 677-079-9
• SMILES: CC(CCN)CO

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.450, Calc.^*
• Boiling Point: 174.7±23.0 °C (760 mmHg), Calc.^*
• Flash Point: 59.4±22.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

4-Amino-2-methyl-1-butanol is an organic compound with the molecular formula C5H13NO, characterized by an amino group (-NH2) and a hydroxyl group (-OH) attached to a branched butane backbone. This compound was initially synthesized in the early 20th century as part of research into alkanolamines, a group of compounds that show promise due to their unique dual functionality. As both an amine and an alcohol, 4-amino-2-methyl-1-butanol can undergo a range of chemical reactions, making it valuable as a versatile intermediate in organic synthesis and a precursor in pharmaceutical development.

One of the primary applications of 4-amino-2-methyl-1-butanol is in the synthesis of active pharmaceutical ingredients (APIs), where it serves as a precursor to beta-adrenergic blocking agents and other bioactive molecules. Its structural features allow for selective modification, enabling chemists to construct complex molecules with specific therapeutic properties. For instance, the amino group can undergo acetylation or be used to create amide bonds, while the hydroxyl group can be transformed into esters or other reactive groups, expanding its use in producing a wide range of drugs with targeted effects.

Additionally, 4-amino-2-methyl-1-butanol has found applications in the production of surfactants and emulsifiers for personal care products and cosmetics. The combination of hydrophilic (amine and hydroxyl) groups and a hydrophobic alkyl chain endows it with surfactant-like properties, allowing it to stabilize emulsions in formulations such as lotions and creams. Its relatively mild and skin-friendly profile further supports its use in formulations for sensitive skin, where stability and safety are critical.

In recent years, 4-amino-2-methyl-1-butanol has also gained attention in the production of specialty polymers, particularly in polyurethanes and polyamides. When used as a chain extender, the amino and hydroxyl groups contribute to the formation of durable polymers with enhanced elasticity and resilience. These properties are beneficial in creating adhesives, coatings, and sealants that require flexibility and adhesion.

Overall, 4-amino-2-methyl-1-butanol’s combination of functional groups provides it with broad applicability across pharmaceuticals, personal care, and polymer science. Its adaptability in chemical transformations continues to make it an attractive compound for researchers and manufacturers seeking to develop new materials and products.

References

1981. A simple synthesis of (E)-3-formylbut-2-enenitrile, and its use as a precursor of isotope-labelled zeatin and (±) dihydrozeatin. Cellular and Molecular Life Sciences, 37(6).
DOI: 10.1007/bf01990038

2004. Synthesis and Application of a New Bisphosphite Ligand Collection for Asymmetric Hydroformylation of Allyl Cyanide. The Journal of Organic Chemistry, 69(11).
DOI: 10.1021/jo040128p