(2R)-1-aminopropan-2-ol

• ChemBase ID: 87369
• Molecular Formular: C3H9NO
• Molecular Mass: 75.10966
• Monoisotopic Mass: 75.06841391
• SMILES: NC[C@@H](C)O
• Canonical SMILES: C[C@H](CN)O
• InChI: InChI=1S/C3H9NO/c1-3(5)2-4/h3,5H,2,4H2,1H3/t3-/m1/s1
• InChIKey: HXKKHQJGJAFBHI-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-aminopropan-2-ol
• IUPAC Traditional name: (R)-1-amino-2-propanol
• Synonyms: (2S)-(+)-1-Aminopropan-2-ol; (-)-Isopropanolamine; (R)-(-)-1-Amino-2-propanol; (2R)-1-aminopropan-2-ol; (R)-(-)-Isopropanolamine; (R)-1-Aminopropan-2-ol; (-)-异丙醇胺; (R)-(-)-1-氨基-2-丙醇

Database IDs

• CAS Number: 2799-17-9; 2799-16-8
• EC Number: 220-532-9
• MDL Number: MFCD00064428
• Beilstein Number: 1718869
• PubChem SID: 24846300; 162074473; 24854348
• PubChem CID: 439938

CALCULATED PROPERTIES

• Acid pKa: 15.304407
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -3.8963997
• LogD (pH = 7.4): -3.0420208
• Log P: -0.89898586
• Molar Refractivity: 20.6299 cm^3
• Polarizability: 8.402709 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 24°C; 24-26 °C(lit.); 24-26°C
• Boiling Point: 160 °C(lit.); 160°C; 160°C
• Flash Point: 159.8 °F; 71 °C; 71°C; 71°C(159°F)
• Auto Ignition Point: 635 °F
• Density: 0.954; 0.954 g/mL at 25 °C(lit.); 0.960
• Refractive Index: 1.4482; n20/D 1.448; n20/D 1.4482(lit.)
• Vapor Pressure: <1 mmHg ( 20 °C)
• Vapor Density: 2.6 (vs air)
• Optical Rotation: [α]/D -23.5±2°, c = 1% in methanol; [α]20/D -23.5°, c = 1 in methanol; -18 (c=1.8 in water)
• Hydrophobicity(logP): -0.986

Safety Information

• Storage Warning: Corrosive; Hygroscopic
• RTECS: UA5775000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3259; UN3259
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45; 23-26-36-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H312
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3259 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95%; 98%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Impurities: ≤1% water
• Linear Formula: CH3CH(OH)CH2NH2

DETAILS

Sigma Aldrich - 238856

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 09281

Other Notes
Used for the preparation of chiral enamines1; Synthesis of 2-methylaziridine2; Use as chiral ligand3

REFERENCES

• For an extensive review of the use of 1,2-amino alcohols as chiral auxiliaries in asymmetric synthesis, see: Chem. Rev., 96, 835 (1996).