2026-48-4

Basic information

• Product Name: (S)-(+)-2-Amino-3-methyl-1-butanol
• Synonyms: L-VALINAL;(+)-L-VALINOL;L-(+)-VALINOL;L-VALINOL;L-2-AMINO-3-METHYL-1-BUTANOL;l-2-amino-3-methylbutan-1-ol;H-VALINOL;H-VAL-OL
• CAS NO: 2026-48-4
• Molecular Formula: C₅H₁₃NO
• Molecular Weight: 103.16
• EINECS: 217-975-5
• Product Categories: Pharmaceutical Intermediates;Amines;blocks;Amino Alcohols;Amino Acid Derivatives;Valine [Val, V];Amino Alcohols (Chiral);Asymmetric Synthesis;Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Compound;Amino alcohols
• Mol File: 2026-48-4.mol
• Article Data: 134

Chemical Properties

• Melting Point: 30-34 °C
• Boiling Point: 81 °C8 mm Hg(lit.)
• Flash Point: 196 °F
• Appearance: Clear slightly yellow/Liquid After Melting
• Density: 0.926 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.182mmHg at 25°C
• Refractive Index: n20/D 1.4548(lit.)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.82±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 1719137
• CAS DataBase Reference: (S)-(+)-2-Amino-3-methyl-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-Amino-3-methyl-1-butanol(2026-48-4)
• EPA Substance Registry System: (S)-(+)-2-Amino-3-methyl-1-butanol(2026-48-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-24/25-36
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 2026-48-4(Hazardous Substances Data)

Usage

Description

(S)-(+)-2-Amino-3-methyl-1-butanol is a white to light yellow crystalline powder that is an optically active amino alcohol. It is a chiral compound, with the (S)-configuration indicating the spatial arrangement of its atoms in three-dimensional space. (S)-(+)-2-Amino-3-methyl-1-butanol is known for its unique chemical properties and versatile applications across various industries.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-2-Amino-3-methyl-1-butanol is used as a reagent for the synthesis of small-molecule inhibitors of MDM2-p53 protein-protein interaction (MDM2 inhibitors). These inhibitors are in clinical trials for the treatment of cancer, as they can potentially disrupt the interaction between MDM2 and p53 proteins, leading to the activation of p53's tumor-suppressing functions.
Used in Chemical Synthesis:
(S)-(+)-2-Amino-3-methyl-1-butanol is used as a reagent in the synthesis of simple 1,3-thiazolidine-2-thione derivatives, which can exhibit fungicidal activity. This application is particularly relevant in the agricultural and pharmaceutical industries, where fungicides are essential for controlling fungal infections and protecting crops.
Used in Chiral Ligand Synthesis:
(S)-(+)-2-Amino-3-methyl-1-butanol can be used to prepare chiral oxazoline-derived multidentate ligands containing a cyclophosphazene moiety. These ligands are valuable in asymmetric catalysis, a field that focuses on the selective synthesis of chiral compounds with a single enantiomer. The use of chiral ligands can improve the efficiency and selectivity of chemical reactions, leading to the production of enantiomerically pure products.
Used in Organic Chemistry:
(S)-(+)-2-Amino-3-methyl-1-butanol can also be used to prepare imines and oxazolines by reacting with aldehydes and nitriles, respectively. Imines are important intermediates in organic synthesis, while oxazolines are useful as chiral building blocks in the construction of complex organic molecules. The ability of (S)-(+)-2-Amino-3-methyl-1-butanol to form these compounds makes it a valuable starting material in the synthesis of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.

Purification Methods

Purify S-valinol by vacuum distillation using a short Vigreux column (p 11). Alternatively it is purified by steam distillation. The steam distillate is acidified with HCl; the aqueous layer is collected and evaporated. The residue is dissolved in butan-1-ol, filtered and dry Et2O added to crystallise the hydrochloride salt (hygroscopic), m 113o. The free base can be obtained by suspending the salt in Et2O and adding small volumes of saturated aqueous K2CO3 until effervescence is complete and the mixture is distinctly alkaline. At this stage the aqueous layer should appear as a white sludge. The mixture is heated to boiling and refluxed for 30minutes (more Et2O is added if necessary). Purification of Biochemicals — Amino Acids and Peptides The Et2O layer is decanted off from the white sludge, the sludge is extracted twice with Et2O (by boiling for a few minutes), the combined organic layers are dried (KOH pellets), evaporated and the residue is distilled in a vacuum. [Nagao et al. J Org Chem 55 1148 1990, Beilstein 4 III 805.]

InChI:InChI=1/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m0/s1

Upstream product

• 17431-03-7 L-valine ethyl ester 
• 72-18-4 L-valine 
• 23262-05-7 N-Benzoyl-Gly-Val-OEt 
• 4070-48-8 L-Valine methyl ester 
• 42807-42-1 N-benzyl-L-valinol 
• 82193-75-7 L-Prolyl-leucyl-α-aminoisobutyryl-α-aminoisobutyryl-α-glutamyl-valinol 
• 82193-74-6 L-Pro-L-Leu-Aib-D-Iva-L-Glu-L-Vol 
• 82417-07-0 (1S,1'S)-(+)-N-(2'-hydroxy-1'-isopropylethyl)-1,2-diphenylethylamine 
• 93684-34-5 (4S,Z)-2-ethylidene-4-(1-methylethyl)-3-(2-propenyl)oxazolidine 
• 102922-31-6 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 102922-32-7 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-propyl-1,2,3,4-tetrahydro-isoquinoline 
• 119109-81-8 (R)-1-Butyl-2-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline 
• 102922-33-8 (R)-1-Benzyl-2-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-1,2,3,4-tetrahydro-isoquinoline 
• 119109-86-3 (R)-2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-1-(2-methoxy-benzyl)-1,2,3,4-tetrahydro-isoquinoline 

Downstream Products

• 24629-28-5 N-(2,4,6-Trinitro-phenyl)-L-valinol 
• 64715-88-4 (S)-2-amino-1-methoxy-3-methylbutane 
• 149065-76-9 (S)-4-isopropyl-2-(thiophen-2-yl)-4,5-dihydrooxazole 
• 131380-85-3 (-)-1,3-bis<(S)-4-isopropyl-4,5-dihydro-oxazol-2-yl>benzene 
• 108915-04-4 2-[(4S)-4-iso-propyl-4,5-dihydro-1,3-oxazol-2-yl]pyridine 
• 84272-19-5 (4S)-4-isopropyl-1,3-oxazolidine-2-thione 
• 113336-47-3 (S)-N-(1-iso-propyl-2-hydroxyethyl)benzoylformamide 
• 139192-50-0 (2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol 
• 131380-91-1 1-[(4'S)-4'-isopropyl-4',5'-dihydrooxazol-2'-yl]-2-hydroxybenzene 
• 91757-35-6 4-Chloro-N-hydroxy-N'-(1-hydroxymethyl-2-methyl-propyl)-benzamidine 
• 143508-85-4 (S)-2-(N-3',5'-dibromosalicylidene)-amino-3-methyl-1-butanol 
• 155631-48-4 (S)-4,5-dihydro-α,α-dimethyl-4-isopropyloxazole-2-ethanol 
• 155052-31-6 2,4-di-tert-butyl-6-({[(1S)-1-(hydroxymethyl)-2-methylpropyl]imino}methyl)phenol 
• 83537-86-4 N-[(benzyloxy)carbonyl]-glutaminyl-valinol 

Relevant articles and documents

One-pot synthesis of new chiral sulfides and selenides containing oxazolidines: Catalyst in the enantioselective addition of diethylzinc to benzaldehyde

A new easily accessible class of chiral sulfides 1 and selenides 2 containing oxazolidine was prepared from amino acids. They were used as chiral ligands in the catalytic asymmetric addition of diethylzinc to benzaldehyde to give the corresponding seconda

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Enantioselective Synthesis of α-Functionally Substituted Cyclic Ketones via Chiral Organotin Enamines

Chiral organotin enamines 1a-f are easily prepared from cyclic ketones, chiral amino alcohols 5a-c (derived from amino acids), and an organotin precursor.Nucleophilic addition of these compounds to electrophilic alkenes followed by hydrolysis leads to the

Synthesis and characterization of chiral ionic liquids based on quinine, L-proline and L-valine for enantiomeric recognition

The separation of enantiomers remains a major challenge for the pharmaceutical industry. In this work, eight chiral ionic liquids (CILs) directly derived from the ‘chiral pool’ were synthesized and characterized in order to develop enantioselective systems, for the chiral resolution. According to their chiral cations, three different groups of CILs were prepared, namely based on quinine, L-proline and L-valine, and their enantiomeric recognition ability evaluated. For that purpose the diastereomeric interactions between a racemic mixture of Mosher's acid sodium salt and each CIL were studied using 19F NMR spectroscopy. The remarkable chemical shift dispersion induced by some CILs demonstrates their potential application in chiral resolution. Additionally the optical rotation, thermophysical properties and ecotoxicity against the marine bacteria Aliivibrio fischeri of these chiral ionic liquids were addressed.

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

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In the last two decades, tubulysins have emerged as alternatives to microtubule depolymerizing agents such as colchicine and vinblastine, which are well-established anticancer agents. However, the complex structure of tubulysins has always posed a challen