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Basic Information
| CAS No.: | 118-10-5 |
|---|---|
| Name: | Cinchonine |
| Article Data: | 21 |
| Molecular Structure: | |
|
|
|
| Formula: | C19H22N2O |
| Molecular Weight: | 294.396 |
| Synonyms: | (S)-[(5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;Quinoline alkaloid;.alpha.-Quinidine;Prestwick_501;(9S)-Cinchonan-9-ol;(S)-[(4R,5S,7S)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;[(5S,7R)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;D-Cinchonine;Cinchonan-9-ol, (9S)-;2-Quinuclidinemethanol, .alpha.-(5-vinyl-2-quinolyl)-;4-quinolyl(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol;(+)-Cinconine; |
| EINECS: | 204-234-6 |
| Density: | 1.2 g/cm3 |
| Melting Point: | 256-266 °C |
| Boiling Point: | 464.5 °C at 760 mmHg |
| Flash Point: | 234.7 °C |
| Solubility: | insoluble in water |
| Appearance: | white to light yellow crystal powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 20/21/22 |
| Safety: | 26-36-36/37 |
| PSA: | 36.36000 |
| LogP: | 3.10250 |
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Synthetic route
- 189309-24-8
O-tosylcinchonine
A
- 1393446-38-2
(Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate
B
- 118-10-5
Cinchonin
Conditions
| Conditions | Yield |
|---|---|
| With salicylic acid In ethylene glycol at 95℃; for 0.5h; Microwave irradiation; | A 60% B 15% C 15% |
...Expand
- 560119-43-9
methanesulfonic acid (quinolin-4-yl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methyl ester
A
- 118-10-5
Cinchonin
C
- 560119-45-1
(1S,2R,3S,5S,6R)-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol
Conditions
| Conditions | Yield |
|---|---|
| With water; tartaric acid at 100℃; Title compound not separated from byproducts; | A n/a B n/a C 48% D 1% |
...Expand
...Expand
...Expand
Conditions
| Conditions | Yield |
|---|---|
| at 60 - 70℃; |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| at 150 - 160℃; im Rohr; isomer(ic) I; |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| With dibutyltin(II) dilaurate In toluene at 110℃; for 48h; | 99% |
Conditions
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -10 - 50℃; for 6h; Inert atmosphere; Schlenk technique; | 99% |
| In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere; |
- 24463-19-2
anthracenylmethyl chloride
- 118-10-5
Cinchonin
Conditions
| Conditions | Yield |
|---|---|
| In toluene at 110℃; for 2h; | 98% |
| In toluene Reflux; | 94% |
| In toluene for 24h; Heating; | 80% |
Conditions
| Conditions | Yield |
|---|---|
| In tetrahydrofuran; N,N-dimethyl-formamide Reflux; | 98% |
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Cinchonine
Chemistry
The molecular formula of Cinchonine(118-10-5) is C19H22N2O and its formula weight is 294.39.
Cinchonine(118-10-5) has a melting point of 260-263 °C.
The chemical synonyms of Cinchonine(118-10-5) are D-CINCHONINE;(+)-CINCHONINE;CINCHONINE;CINCHONAN-9-OL,(9S)-;(+)-cinconine;(8r,9s)-cinchonine;(9s)-cinchonan-9-o;(9S)-Cinchonan-9-ol
The molecular structure of Cinchonine(118-10-5):
Cinchonine(118-10-5) has a melting point of 260-263 °C.
The chemical synonyms of Cinchonine(118-10-5) are D-CINCHONINE;(+)-CINCHONINE;CINCHONINE;CINCHONAN-9-OL,(9S)-;(+)-cinconine;(8r,9s)-cinchonine;(9s)-cinchonan-9-o;(9S)-Cinchonan-9-ol
The molecular structure of Cinchonine(118-10-5):
Toxicity Data With Reference
| 1. | ipr-rat LD50:152 mg/kg | APTOA6 Acta Pharmacologica et Toxicologica. 4 (1948),265. | ||
| 2. | scu-mus LDLo:400 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 205 (1948),129. | ||
| 3. | scu-frg LDLo:200 mg/kg | AEPPAE Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 205 (1948),129. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes Xn
Risk Statements 20/22-20/21/22
Safety Statements 26-36-36/37
RIDADR 1544
WGK Germany 3
RTECS GD3500000
F 8-34
HazardClass 6.1(b)
PackingGroup III
Hazard Codes Xn
Risk Statements 20/22-20/21/22
Safety Statements 26-36-36/37
RIDADR 1544
WGK Germany 3
RTECS GD3500000
F 8-34
HazardClass 6.1(b)
PackingGroup III
Specification
Chemical Stability: Stable under normal temperatures and pressures.
Conditions to Avoid: Incompatible materials, light.
Incompatibilities with Other Materials Strong oxidizing agents, strong reducing agents, strong bases.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization Has not been reported.
Conditions to Avoid: Incompatible materials, light.
Incompatibilities with Other Materials Strong oxidizing agents, strong reducing agents, strong bases.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization Has not been reported.