(3R)-pyrrolidin-3-ol

• ChemBase ID: 59248
• Molecular Formular: C4H9NO
• Molecular Mass: 87.12036
• Monoisotopic Mass: 87.06841391
• SMILES: N1C[C@@H](CC1)O
• Canonical SMILES: O[C@H]1CNCC1
• InChI: InChI=1S/C4H9NO/c6-4-1-2-5-3-4/h4-6H,1-3H2/t4-/m1/s1
• InChIKey: JHHZLHWJQPUNKB-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-pyrrolidin-3-ol
• IUPAC Traditional name: (3R)-pyrrolidin-3-ol
• Synonyms: (3R)-Pyrrolidin-3-ol; (3R)-3-Hydroxypyrrolidine; (R)-3-Hydroxypyrrolidine; (R)-3-Pyrrolidinol; (R)-Pyrrolidin-3-ol; (R)-(+)-3-Pyrrolidinol; (R)-(+)-3-Hydroxypyrrolidine; (3R)-Pyrrolidin-3-ol; (R)-3-羟基吡咯烷; (R)-3-吡咯烷醇; (R)-(+)-3-羟基四氢吡咯/吡咯烷

Database IDs

• CAS Number: 2799-21-5; 83220-72-8
• MDL Number: MFCD00145220; MFCD00005256
• Beilstein Number: 5376132; 4652606
• PubChem SID: 24863928; 24880171; 162064011
• PubChem CID: 2759337

CALCULATED PROPERTIES

• Acid pKa: 14.857613
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -4.1708517
• LogD (pH = 7.4): -3.8556705
• Log P: -0.93477863
• Molar Refractivity: 23.5523 cm^3
• Polarizability: 9.517664 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 15 - 17°C; 15°C; 15°C
• Boiling Point: 108-110°C/8mm; 215-216 °C(lit.); 215-216°C
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• Density: 1.048; 1.078; 1.078 g/mL at 20 °C(lit.)
• Refractive Index: 1.4900; n20/D 1.488(lit.); n20/D 1.490
• Optical Rotation: [α]20/D +6.5±1°, c = 3.5% in methanol (as free base); [α]20/D +6.5°, c = 3.5 in methanol; +6.5 (c=3.5 in methanol)
• Hydrophobicity(logP): -0.927

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic; IRRITANT; Irritant/Air Sensitive/Hygroscopic/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95%; 98%; 99%, ee 99%
• Grade: purum
• Impurities: <2% tetraethylene glycol dimethyl ether
• Empirical Formula (Hill Notation): C4H9NO

DETAILS

Sigma Aldrich - 382981

Packaging
1, 5 g in glass bottle
Application
Used as a ligand in the enantioselective addition of diethylzinc to aromatic aldehydes leading to optically active secondary alcohols.1 Also used to prepare-κ-opioid receptor agonists.2

Sigma Aldrich - 56435

Caution
may discolor to yellow on storage
Other Notes
The free base has a positive optical rotation whereas the hydrochloride gives a negative value1; Chiral building block2,3; Often-used beneficial group in pyridone carboxylic acid antibacterials4

REFERENCES

• Product of Toray Industries, Inc.