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(R)-(-)-3-Quinuclidinol
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Name

(R)-(-)-3-Quinuclidinol

 EINECS 246-857-6
CAS No. 25333-42-0 Density 1.13 g/cm3
PSA 23.47000 LogP 0.01080
Solubility 100 g/100 mL Melting Point 217-224 °C
Formula C7H13NO Boiling Point 206.9 °C at 760 mmHg
Molecular Weight 127.186 Flash Point 97.7 °C
Transport Information UN 3263 Appearance White solid
Safety 45-36/37/39-26-16 Risk Codes 34-11
Molecular Structure Molecular Structure of 25333-42-0 ((R)-(-)-3-Quinuclidinol) Hazard Symbols FlammableF, CorrosiveC
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;

Article Data 51

(R)-(-)-3-Quinuclidinol Synthetic route

3731-38-2

3-Quinuclidinone

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
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%

(3R)-1-azabicyclo[2.2.2]octan-3-ol hydrochloride

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
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
ConditionsYield
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

C7H13NO*C18H14O8

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
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
ConditionsYield
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%

(R)-3-acetoxyquinuclidinium L-tartrate

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
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
ConditionsYield
With sodium hydroxide at 50℃; for 1h;80%
1619-34-7

3-quinuclidinol

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
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

3-Methoxymethoxy-1-aza-bicyclo[2.2.2]octane

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
ConditionsYield
With hydrogenchloride; water for 0.25h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
174590-62-6

(R)-quinuclidin-3-yl benzoate

A

65-85-0

benzoic acid

B

25333-42-0

(R)-quinuclidin-3-ol

Conditions
ConditionsYield
With horse serum butyrycholinesterase; water In phosphate buffer at 30℃; pH=7.4; Enzyme kinetics;

(R)-(-)-3-Quinuclidinol Chemical Properties

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

(R)-(-)-3-Quinuclidinol Safety Profile

Safety Information of (R)-(-)-3-Quinuclidinol (CAS NO.25333-42-0):
Hazard Codes: CCorrosive,FFlammable
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

(R)-(-)-3-Quinuclidinol Specification

 (R)-(-)-3-Quinuclidinol , its CAS NO. is 25333-42-0, the synonym is (R)-Quinuclidin-3-ol .

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