(2S)-2-amino-3-methylbutan-1-ol

• ChemBase ID: 3975
• Molecular Formular: C5H13NO
• Molecular Mass: 103.16282
• Monoisotopic Mass: 103.09971404
• SMILES: CC(C)[C@H](N)CO
• Canonical SMILES: OC[C@H](C(C)C)N
• InChI: InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m1/s1
• InChIKey: NWYYWIJOWOLJNR-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-methylbutan-1-ol
• IUPAC Traditional name: L-valinol
• Synonyms: L-Valinol; (S)-(+)-2-Amino-3-methyl-1-butanol; (S)-2-Amino-3-methylbutanol; 2-Amino-3-methyl-1-butanol; 2-amino-3-methylbutan-1-ol; L-Valinol; (S)-2-Amino-3-methyl-butan-1-ol; L-Valinol; (S)-(+)-2-Amino-3-methyl-1-butanol; (S)-(+)-2-Amino-3-methyl-1-butanol; S)-(+)-2-Amino-3-methyl-1-butanol; (2S)-2-amino-3-methylbutan-1-ol; L-(+)-Valinol; (S)-(+)-2-氨基-3-甲基-1-丁醇; L-缬氨醇; L-缬氨醇; (S)-(+)-2-氨基-3-甲基-1-丁醇

Database IDs

• CAS Number: 2026-48-4
• EC Number: 217-975-5
• MDL Number: MFCD00063850; MFCD00064296
• Beilstein Number: 1719137
• PubChem SID: 160967410; 24851236; 24890042; 46508380
• PubChem CID: 640993

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.1198635
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -3.0263493
• LogD (pH = 7.4): -2.4011502
• Log P: -0.011490631
• Molar Refractivity: 29.6255 cm^3
• Polarizability: 12.084012 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.3
• LOG S: 0.44
• Solubility (Water): 2.86e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 30 - 34°C; 30-32 °C(lit.); 30-32°C; 30-34 °C
• Boiling Point: 189-190 °C(lit.); 81 °C/8 mmHg(lit.); 81°C/8mm
• Flash Point: 172.4 °F; 78 °C
• Density: 0.926 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4548(lit.)
• Optical Rotation: [α]20/D +10±1°, c = 10% in H2O; [α]25/D +10°, c = 10 in H2O
• Hydrophobicity(logP): -0.058

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC/NT); 95%; 96%; 97%
• Grade: purum
• Optical Purity: ee: 95% (GLC)
• Linear Formula: (CH3)2CHCH(NH2)CH2OH
• Empirical Formula (Hill Notation): C5H13NO

DETAILS

MP Biomedicals - 02199475

M.P.=30-32°C
Density=0.926

DrugBank - DB04383

Drug information: experimental

Sigma Aldrich - 186708

Packaging
1, 5, 25 g in glass bottle
Application
Reacts with aldehydes and nitriles to form imines1 and oxazolines,2 respectively, for asymmetric synthesis.

Sigma Aldrich - 94672

Other Notes
Important chiral auxiliary and building block; preparation of 4-isopropyloxazolidinones, employed in stereocontrolled aldol and alkylation reactions 1; Synthesis of chiral 2-thiazolidinethiones for aldol reactions 2; Asymmetric alkylation of condensation product with keto acids 3; Asymmetric reactions of its amidines and imines 4; Oxidation of N-protected derivative to the aldehyde 5