Cinchonine supplier | CasNO.118-10-5

Name
Cinchonine
EINECS 204-234-6
CAS No. 118-10-5
Article Data21
CAS DataBase
Density 1.2 g/cm³
Solubility insoluble in water
Melting Point 256-266 °C
Formula C₁₉H₂₂N₂O
Boiling Point 464.5 °C at 760 mmHg
Molecular Weight 294.396
Flash Point 234.7 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-36/37
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xn
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;
PSA 36.36000
LogP 3.10250

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

C: 118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3
(+)-cinchonine

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

B: 118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3
(+)-cinchonine

C: 560119-45-1
(1S,2R,3S,5S,6R)-2-(quinolin-4-yl)-6-vinyl-1-azabicyclo[3.2.2]nonan-3-ol

D: (E)-cinchene

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

: 14509-68-3, 14528-54-2, 72402-48-3, 72402-49-4
cinchonan-9-one

: 64-19-7
acetic acid

iron powder: iron powder

: 118-10-5
Cinchonin

...Expand

: 14509-68-3, 14528-54-2, 72402-48-3, 72402-49-4
cinchonan-9-one

: 64-17-5
ethanol

sodium: sodium

: 118-10-5
Cinchonin

...Expand

: 14402-57-4
benzoylcinchonine

alcoholic KOH-solution: alcoholic KOH-solution

A: 65-85-0
benzoic acid

B: 118-10-5
Cinchonin

Conditions

Conditions	Yield
at 60 - 70℃;

...Expand

: (9S,10Ξ)-10-iodo-10,11-dihydro-cinchonan-9-ol; dihydriodide hydrate

water: water

A: 118-10-5
Cinchonin

B: 7299-23-2
9,10-Epoxy-10,11-dihydro-cinchonan

C apocinchonine: apocinchonine

Conditions

Conditions	Yield
at 150 - 160℃; im Rohr; isomer(ic) I;

...Expand

: 118-10-5
Cinchonin

: 1609-86-5
Tert-butyl isocyanate

: (9S)-9-deoxy-cinchonin-9-yl tert-butylcarbamate

Conditions

Conditions	Yield
With dibutyltin(II) dilaurate In toluene at 110℃; for 48h;	99%

: 917-54-4
methyllithium

: 118-10-5
Cinchonin

: 2'-methylcinchonine

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

: (2R,5R,1'S)-1-(9-anthracenyl)methyl-5-ethylene-2-[1-hydroxy-1-(quinol-4-yl)]methyl-1-azoniabicyclo[2.2.2]octane chloride

Conditions

Conditions	Yield
In toluene at 110℃; for 2h;	98%
In toluene Reflux;	94%
In toluene for 24h; Heating;	80%

: (1E,4E)-1,5-bis(4-(bromomethyl)phenyl)penta-1,4-dien-3-one

: 118-10-5
Cinchonin

: C57H60N4O3(2+)*2Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran; N,N-dimethyl-formamide Reflux;	98%

: 92642-09-6
5,5'-bis(bromomethyl)-2,2'-bipyridine

: 118-10-5
Cinchonin

: C50H54N6O2(2+)*2Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran Reflux;	96%

: 100-44-7
benzyl chloride

: 118-10-5
Cinchonin

: 69221-14-3
(9S)-9-hydroxy-1-(phenylmethyl)-cinchonanium chloride

Conditions

Conditions	Yield
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃; for 10h;	95%
With ethanol
In N,N-dimethyl-formamide at 80℃; for 3h; N-quaternization;

: 60682-97-5, 66888-72-0, 29477-66-5
(1E)-1,2-bis[3-(bromomethyl)phenyl]diazene

: 118-10-5
Cinchonin

: C54H58N4O2(2+)*2Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran; acetonitrile Reflux;	95%

: 98-59-9
p-toluenesulfonyl chloride

: 118-10-5
Cinchonin

: 189309-24-8
O-tosylcinchonine

Conditions

Conditions	Yield
Stage #1: Cinchonin With sodium hydride In tetrahydrofuran at 70℃; for 2h; deprotonation; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 60 - 70℃; for 10h; Tosylation;	94%
With tributyl-amine; potassium hydroxide In dichloromethane; water at 20℃; for 24h;	90%
With pyridine

: 118-10-5
Cinchonin

: 485-65-4
dihydrocinchonine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 10h;	92%
With sulfuric acid; palladium Hydrogenation;
With palladium; acetic acid Hydrogenation;

: 118-10-5
Cinchonin

: 74-88-4
methyl iodide

: (1S,4S,5R)-2-((S)-methoxy(quinolin-4-yl)methyl)-5-vinylquinuclidine

Conditions

Conditions	Yield
Stage #1: Cinchonin With potassium hydride In N,N-dimethyl-formamide; mineral oil; pentane at 0 - 50℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil; pentane at 0 - 20℃; Inert atmosphere;	91%
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃;	60%
Stage #1: Cinchonin With potassium hydride In tetrahydrofuran; mineral oil at 0 - 50℃; for 3h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;	59%

: 876-08-4
p-(chloromethyl)benzoyl chloride

: 118-10-5
Cinchonin

: C27H27ClN2O2

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 16h;	90%

: 124-63-0
methanesulfonyl chloride

: 118-10-5
Cinchonin

: 560119-43-9
methanesulfonic acid (quinolin-4-yl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methyl ester

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	88%

: 622-95-7
4-chlorobenzyl bromide

: 118-10-5
Cinchonin

: N-(4-chlorobenzyl)cinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 5.5h; Reflux;	87.8%
In tetrahydrofuran for 84h; Heating;	52%

: 100-44-7
benzyl chloride

: 118-10-5
Cinchonin

: 1261665-86-4
O-benzylcinchonine

Conditions

Conditions	Yield
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil	87%
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: benzyl chloride In N,N-dimethyl-formamide; mineral oil	86%

: 106-95-6
allyl bromide

: 118-10-5
Cinchonin

: 852951-76-9
O-allylcinchonine

Conditions

Conditions	Yield
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil	87%
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil	87%
Stage #1: Cinchonin With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;	87%
With sodium hydride In N,N-dimethyl-formamide at 30℃; for 2h;	87%

: 100-39-0
benzyl bromide

: 118-10-5
Cinchonin

: (1S,2R,4S,5R)-1-benzyl-2-((S)-(1-benzylquinolin-1-ium-4-yl)(hydroxy)methyl)-5-vinylquinuclidin-1-ium bromide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide; isopropyl alcohol at 70℃; for 12h; Inert atmosphere;	87%

: 29133-99-1
4,6-dichloro-2,5-diphenylpyrimidine

: 118-10-5
Cinchonin

: C35H31ClN4O

Conditions

Conditions	Yield
With potassium hydroxide In toluene for 1h; Inert atmosphere; Reflux;	87%

: 100-39-0
benzyl bromide

: 118-10-5
Cinchonin

: 85653-34-5
(+)-N-benzylcinchonineammonium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 4.5h; Reflux;	86.9%
In tetrahydrofuran for 16h; Reflux;	82%
In acetonitrile at 20℃; for 24h; Inert atmosphere;

: C27H31Br

: 118-10-5
Cinchonin

: C46H53N2O(1+)*Br(1-)

Conditions

Conditions	Yield
In tetrahydrofuran for 16h; Reflux;	86%

: 32247-96-4
3,5-bis(trifluoromethyl)benzyl bromide

: 118-10-5
Cinchonin

: N1-3,5-bis(trifluoromethyl)benzylcinchonium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Heating;	85%
In tetrahydrofuran for 24h; Reflux;	79%
In toluene at 80℃; Inert atmosphere;	72%

: 108-30-5
succinic acid anhydride

: 118-10-5
Cinchonin

: C23H26N2O4

Conditions

Conditions	Yield
With dmap In dichloromethane at 50℃;	84%

: 939-26-4
2-bromomethylnaphthyl bromide

: 118-10-5
Cinchonin

: 207561-98-6
N-(2-napthylmethyl)cinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 16h; Reflux;	83%

: 40400-13-3
2-Iodobenzyl bromide

: 118-10-5
Cinchonin

: 1410875-87-4
N-2-iodobenzylcinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 12h; Reflux; Inert atmosphere;	82%

: 611-17-6
1-bromomethyl-2-chlorobenzene

: 118-10-5
Cinchonin

: 1261665-70-6
N-(2-chlorobenzyl)cinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 6h; Reflux;	81.2%

: 118-10-5
Cinchonin

: (8R,9R)-9-amino(9-deoxy)epicinchonin

Conditions

Conditions	Yield
Stage #1: Cinchonin With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: With diphenylphosphoranyl azide In tetrahydrofuran at 0 - 50℃; Inert atmosphere; Stage #3: With hydrogenchloride In dichloromethane; water	81%
Stage #1: Cinchonin With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: With ammonia In tetrahydrofuran; chloroform at 0 - 60℃;	78%
Multi-step reaction with 2 steps 1.1: diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 50 °C 2.1: triphenylphosphine / 15 h / 50 °C 2.2: 24 h / 20 °C View Scheme

: 10387-13-0
9,1-bis(chloromethyl)anthracene

: 118-10-5
Cinchonin

: C54H56N4O2(2+)*2Cl(1-)

Conditions

Conditions	Yield
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃;	80%

: 2417-77-8
9-bromoethylanthracene

: 118-10-5
Cinchonin

: 365567-24-4
N-(anthracen-9-ylmethyl)cinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 4.5h; Reflux;	79.6%
In tetrahydrofuran for 8h; Inert atmosphere; Reflux;	71%
In tetrahydrofuran for 16h; Reflux;	52%

: 2746-25-0
p-Methoxybenzyl bromide

: 118-10-5
Cinchonin

: 207561-99-7
N-(4-methoxybenzyl)cinchoninium bromide

Conditions

Conditions	Yield
In tetrahydrofuran for 3.5h; Reflux;	78.6%

: 589-15-1
1-bromomethyl-4-bromobenzene

: 118-10-5
Cinchonin

: N-(p-bromobenzyl)-cinchoninium bromide

Conditions

Conditions	Yield
In chloroform 1.) reflux, 40 min, 2.) room temperature, 19 h;	77%
In tetrahydrofuran for 5.5h; Reflux;	66.3%
In tetrahydrofuran for 44h; Heating;	41%

: 4392-24-9
3-phenylprop-2-en-1-yl bromide

: 118-10-5
Cinchonin

: N-cinnamyl-cinchoninium bromide

Conditions

Conditions	Yield
In chloroform 1.) reflux, 2.) room temperature;	77%

Cinchonine Chemical Properties

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 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.

Cinchonine Consensus Reports

Reported in EPA TSCA Inventory.

Cinchonine Safety Profile

Poison by intraperitoneal and subcutaneous routes. When heated to decomposition it emits toxic fumes of NO_x.
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

Cinchonine 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.

Product Name

Cinchonine

Synthetic route

Cinchonine Chemical Properties

Cinchonine Toxicity Data With Reference

Cinchonine Consensus Reports

Cinchonine Safety Profile

Cinchonine Specification

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