(S)-(+)-2-Amino-3-methyl-1-butanol

• CAS: 2026-48-4
• Catalog Number: ACM2026484
• Category: Main Products
• Molecular Weight: 103.16
• Molecular Formula: C5H13NO
• Description: Valinol is an organic compound named after, and commonly produced from, the amino acid valine. The compound is chiral and is produced almost exclusively as the Sisomer (also designated as the Lisomer), due to the abundant supply of S-valine. It is part of a broader class of amino alcohols
• Synonyms: S-VALINOL;(S)-2-Amino-3-Methyl-1-Butanol;L-Val-ol;Valinol;H-L-VAL-OL
• IUPAC Name: (2S)-2-amino-3-methylbutan-1-ol
• InChI Key: NWYYWIJOWOLJNR-RXMQYKEDSA-N
• Boiling Point: 81°C8mm Hg(lit.)
• Melting Point: 30-32ºC
• Flash Point: 78ºC
• Density: 0.926
• Appearance: White to light yellow crystal powder
• EC Number: 217-975-5
• Exact Mass: 103.10000
• Hazard Codes: Xi
• Hazard Statements: Xi
• HS Code: 29221980
• LogP: 0.66230
• MDL Number: MFCD00064296
• Refractive Index: 1.4538-1.4558
• Safety Description: 26-24/25-36
• Stability: Stable under normal temperatures and pressures. Absorbs carbon dioxide from the air.
• Storage Conditions: 2-8ºC
• Supplemental Hazard Statements: H315-H319
• Symbol: GHS07
• Vapor Pressure: 0.182mmHg at 25°C
• WGK Germany: 3

Case Study

(S)-(+)-2-Amino-3-methyl-1-butanol: An Effective Stabilizer for High-Quality Sol-Gel ZnO Films

Vilà, Anna, et al. Nanomaterials 13.6 (2023): 1057.

The sol-gel synthesis of zinc oxide (ZnO) thin films for optical and electronic devices requires precise control over precursor chemistry to ensure ink stability and final film purity. The choice of molecular stabilizer is critical, as it influences the gelation process, the crystalline phases formed upon annealing, and the ultimate optical properties. In this comparative research, the (S)-(+)-2-Amino-3-methyl-1-butanol was used as a stabilizer in a sol-gel process with zinc acetate dihydrate and 2-methoxyethanol. It functioned as a complexing agent to control the hydrolysis and condensation reactions, forming a stable precursor ink. This ink was drop-coated onto glass and calcined at temperatures from 300°C to 600°C to produce ZnO thin films. Its performance was directly compared to other aliphatic and aromatic aminoalcohols.
Key Performance:
· Superior Ink and Film Stability: Precursor inks formulated with this and other aliphatic aminoalcohols demonstrated significantly greater stability than those with aromatic analogues, which degraded rapidly.
· High Phase Purity: Films derived from this aliphatic stabilizer formed exclusively the hexagonal wurtzite phase of ZnO at all annealing temperatures. In contrast, films made with aromatic stabilizers contained a mixture of wurtzite and cubic sphalerite phases, indicating lower purity.
· Favorable Optical Properties: The optical band gap (Eg) of films made with this aliphatic aminoalcohol was higher, and the Urbach energy (EU)-associated with structural disorder-was lower than in films made with an aromatic counterpart (aminobenzyl alcohol), indicating improved optical quality and fewer defects.

(S)-(+)-2-Amino-3-methyl-1-butanol: A Chiral Building Block for Organometallic Catalysts

Chen, Chong, et al. Journal of Organometallic Chemistry 910 (2020): 121129.

Developing effective chiral ligands is fundamental to advancing asymmetric catalysis, a cornerstone of modern pharmaceutical and fine chemical synthesis. This study demonstrates how (S)-(+)-2-Amino-3-methyl-1-butanol serves as an effective chiral precursor for constructing a library of bidentate Schiff-base ligands used in organometallic chemistry.
In this application, the product was utilized as a key chiral amino alcohol reactant. It underwent a straightforward condensation reaction with various salicylaldehyde derivatives-including salicylaldehyde, 5-nitrosalicylaldehyde, and 3,5-dibromosalicylaldehyde-in refluxing ethanol. This process yielded specific chiral Schiff-base ligands (HL1, HL2, and HL6*), where the product's structure defines the chiral environment. These ligands were subsequently used to synthesize half-sandwich ruthenium(II) complexes.
Key Performance:
Efficient Ligand Synthesis: The condensation reactions using (S)-(+)-2-Amino-3-methyl-1-butanol proceeded efficiently, yielding the target chiral ligands HL1, HL2, and HL6 in high yields of 81%, 82%, and 84%, respectively.
Formation of Defined Complexes: The synthesized ligands successfully coordinated to a ruthenium metal center, forming complexes of the type [(η6-p-cymene)Ru(κ²-N,O-L*)Cl]. Single-crystal X-ray diffraction confirmed the molecular structure of these complexes.
Induction of Chiral Properties: The chiral information from the amino alcohol was transferred to the metal complex. Structural analysis of a related complex suggested the synthesis proceeded without chiral inversion, and the resulting complex exhibited a specific metal-to-ligand charge transfer (MLCT) absorption at 365 nm.