1-azabicyclo[2.2.2]octan-3-ol

• ChemBase ID: 91071
• Molecular Formular: C7H13NO
• Molecular Mass: 127.18422
• Monoisotopic Mass: 127.09971404
• SMILES: N12CCC(C(C1)O)CC2
• Canonical SMILES: OC1CN2CCC1CC2
• InChI: InChI=1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2
• InChIKey: IVLICPVPXWEGCA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-azabicyclo[2.2.2]octan-3-ol
• IUPAC Traditional name: 1-azabicyclo 2.2.2 octan-3-ol
• Synonyms: Quinuclidin-3-ol; 1-Azabicyclo[2.2.2]octan-3-ol; 3-Hydroxyquinuclidine 98%; 3-Quinuclidinol; 3-HYDROXYQUINUCLIDINE; 3-Hydroxyquinuclidine; 3-Quinuclidinol; 1-azabicyclo[2.2.2]octan-3-ol; 3-喹核醇

Database IDs

• CAS Number: 1619-34-7
• EC Number: 216-578-4
• MDL Number: MFCD00151326
• Beilstein Number: 104327
• Merck Index: 148082
• PubChem SID: 162077775
• PubChem CID: 15381

CALCULATED PROPERTIES

• Acid pKa: 14.57555
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.391622
• LogD (pH = 7.4): -1.8484352
• Log P: -0.14292806
• Molar Refractivity: 36.2316 cm^3
• Polarizability: 14.310322 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 217-224°C; 220-223°C; 223 - 224°C
• Hydrophobicity(logP): -0.159

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air Sensitive; Corrosive/Air Sensitive/Store under Argon
• RTECS: VD6191700
• European Hazard Symbols: Corrosive (C)
• UN Number: UN3263
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: 95%; 98+%

DETAILS

MP Biomedicals - 02151313

Crystalline

REFERENCES

• Reagent for selective cleavage of ?-keto esters to ketones in high yield: Synth. Commun., 5, 341 (1975). Geminal diesters are converted to monoesters in high yield under similar conditions: J. Org. Chem., 41, 208 (1976).
• Superior catalyst for the Baylis-Hillman reaction: the addition of acrylic esters to aldehydes, often very slow (4-7 days) with the usual catalyst 1,4-Diazabicyclo[2.2.2]octane, A14003, is much faster (<1 day) in the presence of quinuclidinol: Synth. Commun., 18, 495 (1988); Tetrahedron Lett., 32, 5611 (1991). For more recent discussion and methodology, see: J. Org. Chem., 67, 510 (2002); 68, 692 (2003). For reviews of the Baylis-Hillman reaction, see: Tetrahedron, 44, 4653 (1988); 52, 8001 (1996). The rate of addition of enones to aldehydes is similarly enhanced: Synth. Commun., 18, 495 (1988); 19, 959 (1989).