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| CAS No.: | 25333-42-0 |
|---|---|
| Name: | (R)-(-)-3-Quinuclidinol |
| Molecular Structure: | |
|
|
|
| Formula: | C7H13NO |
| Molecular Weight: | 127.186 |
| Synonyms: | 1-Azabicyclo[2.2.2]octan-3-ol,(R)-;3-Quinuclidinol, (-)- (8CI);(-)-3-Quinuclidinol;(3R)-1-Azabicyclo[2.2.2]octan-3-ol;(3R)-3-Quinuclidinol;(3R)-Quinuclidin-3-ol;(R)-(-)-1-Azabicyclo[2.2.2]octan-3-ol;(R)-1-Azabicyclo[2.2.2]octan-3-ol;(R)-3-Hydroxyquinuclidine;(R)-3-Quinuclidinol;(R)-3-Quinuclidol;R-Quinuclidin-3-ol;l-3-Quinuclidinol; |
| EINECS: | 246-857-6 |
| Density: | 1.13 g/cm3 |
| Melting Point: | 217-224 °C |
| Boiling Point: | 206.9 °C at 760 mmHg |
| Flash Point: | 97.7 °C |
| Solubility: | 100 g/100 mL |
| Appearance: | White solid |
| Hazard Symbols: |
 F,  C
|
| Risk Codes: | 34-11 |
| Safety: | 45-36/37/39-26-16 |
| Transport Information: | UN 3263 |
| PSA: | 23.47000 |
| LogP: | 0.01080 |
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3-Quinuclidinone
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With potassium tert-butylate; hydrogen; RuCl2[(S,S)-xylskewphos] (dmf)n In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity; | 100% |
| With trans-RuCl2((S)-BINAP)((R)-iphan); potassium tert-butylate; hydrogen In isopropyl alcohol at 25℃; under 38002.6 Torr; for 24h; optical yield given as %ee; enantioselective reaction; | 99% |
| With potassium tert-butylate; hydrogen; RuBr2[(S,S)-xylskewphos](6-Me-pica) In ethanol at 30℃; under 7600.51 Torr; for 19h; Product distribution / selectivity; | 95% |
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 20℃; for 0.166667h; | 99% |
| With sodium hydroxide In water at 20℃; for 0.166667h; | 99% |
| With sodium hydroxide In water at 20℃; for 0.166667h; | 99% |
- 1193-65-3
3-quinuclidinone hydrochloride
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With D-glucose In aq. phosphate buffer at 37℃; for 30h; pH=8; Concentration; Temperature; pH-value; Time; | 93% |
| Multi-step reaction with 2 steps 1: sodium; ethanol 2: (1S)-2-oxo-bornane-10-sulfonic acid View Scheme | |
| With R-DAIPEN; potassium tert-butylate; hydrogen; [RuCl(p-cymene)((R)-DM-SEGPHOS)]Cl In isopropyl alcohol at 30℃; under 22502.3 Torr; for 8h; Conversion of starting material; | n/a |
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water; ethyl acetate at 25 - 30℃; for 1h; pH=1 - 2; Resolution of racemate; | 91% |
- 854934-70-6
(3R)-1-azabicyclo[2.2.2]oct-3-yl benzoate (L)-tartrate
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With sodium hydroxide; water In methanol at 50℃; for 10h; | 90% |
| With sodium hydroxide; water In methanol at 50℃; for 10h; | 90% |
| With sodium hydroxide In methanol; water at 50℃; for 10h; | 90% |
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol for 3h; | 82.4% |
| With sodium hydroxide In water at 70℃; for 1h; | 57.3% |
- 59653-40-6
(+)-Aceclidine
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 50℃; for 1h; | 80% |
- 1619-34-7
3-quinuclidinol
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With camphor-10-sulfonic acid | |
| Multi-step reaction with 3 steps 1: 90 percent / 4 h / Heating 3: 80 percent / 2.5N aq. NaOH / 1 h / 50 °C View Scheme | |
| Multi-step reaction with 3 steps 1: 2 h / 20 °C 2: ethanol; water / 0.33 h / 50 °C 3: sodium hydroxide / water / 1 h / 70 °C View Scheme | |
| Multi-step reaction with 3 steps 1: Reflux 2: ethanol / 7 h / 20 °C 3: sodium hydroxide / ethanol / 3 h View Scheme |
A
- 3684-26-2, 25333-42-0, 34583-34-1, 1619-34-7
(S)-quinuclidin-3-ol
B
- 25333-42-0
(R)-quinuclidin-3-ol
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water for 0.25h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
| Conditions | Yield |
|---|---|
| With horse serum butyrycholinesterase; water In phosphate buffer at 30℃; pH=7.4; Enzyme kinetics; |
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Chemistry
Product Name: (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0)
Molecular Formula: C7H13NO
Molecular Weight: 127.18g/mol
Mol File: 25333-42-0.mol
EINECS: 246-857-6
Appearance: White Solid
Melting Point: 217-224 °C
Boiling point: 206.9 °C at 760 mmHg
Storage Temperature: Flammables area
Flash Point: 97.7 °C
Density: 1.13 g/cm3
Water Solubility: 100 g/100 mL
Index of Refraction: 1.549
Molar Refractivity: 35.73 cm3
Molar Volume: 112.2 cm3
Surface Tension: 44.8 dyne/cm
Enthalpy of Vaporization: 51.55 kJ/mol
Vapour Pressure: 0.0545 mmHg at 25°C
XLogP3-AA: 0.2
H-Bond Donor: 1
H-Bond Acceptor: 2
Structure Descriptors of (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0):
IUPAC Name: (8R)-1-azabicyclo[2.2.2]octan-8-ol
Canonical SMILES: C1CN2CCC1C(C2)O
Isomeric SMILES: C1CN2CCC1[C@H](C2)O
InChI: InChI=1S/C7H13NO/c9-7-5-8-3-1-6(7)2-4-8/h6-7,9H,1-5H2/t7-/m0/s1
InChIKey: IVLICPVPXWEGCA-ZETCQYMHSA-N
Product Categories: Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals
Safety Profile
Safety Information of (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0):
Hazard Codes: C
,F
Risk Statements: 34-11
R34:Causes burns.
R11:Highly flammable.
Safety Statements: 45-36/37/39-26-16
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S16:Keep away from sources of ignition.
RIDADR: 3263
Specification
(R)-(-)-3-Quinuclidinol , its CAS NO. is 25333-42-0, the synonym is (R)-Quinuclidin-3-ol .