Product Name

  • Name

    Cinchonidine

  • EINECS 207-622-3
  • CAS No. 485-71-2
  • Article Data21
  • CAS DataBase
  • Density 1.204 g/cm3
  • Solubility insoluble in water
  • Melting Point 204-206 °C(lit.)
  • Formula C19H22N2O
  • Boiling Point 464.502 °C at 760 mmHg
  • Molecular Weight 294.396
  • Flash Point 234.723 °C
  • Transport Information UN 1544
  • Appearance white to light yellow crystal powder
  • Safety 22-24/25-36/37-26
  • Risk Codes 20/21/22-42/43-36/37/38
  • Molecular Structure Molecular Structure of 485-71-2 (Cinchonidine)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Cinchonan-9-ol, (8alpha,9R)-;(R)-[(4R,5S,7R)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(R)-[(5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(R)-[(4S,5S,7R)-5-ethenyl-1-azoniabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;Cinchonan-9-ol, (8R,9R)-;Cinchonan-9-ol, (8-alpha,9R)- (9CI);2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-;(R)-[(4S,5S,7S)-5-ethenyl-1-azabicyclo[2.2.2]oct-7-yl]-quinolin-4-yl-methanol;(8S,9R)-Cinchonidine;alpha-Quinidine;(8-alpha,9R)-Cinchonan-9-ol;
  • PSA 36.36000
  • LogP 3.10250

Synthetic route

cinchonidine diphenylmethylsilyl ether

cinchonidine diphenylmethylsilyl ether

Cinchonidin
485-71-2

Cinchonidin

Conditions
ConditionsYield
With potassium 4-(methoxy)phenyltrifluoroborate In dimethyl sulfoxide at 37℃; for 10h; Inert atmosphere;64%
O-tosylcinchonidine
915134-81-5

O-tosylcinchonidine

A

(Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate
1393446-38-2

(Z)-1-(quinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)prop-1-enyl 4-methylbenzene sulfonate

B

(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane
118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3

(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane

C

Cinchonidin
485-71-2

Cinchonidin

Conditions
ConditionsYield
With salicylic acid In ethylene glycol at 95℃; for 0.25h; Microwave irradiation;A 40%
B 20%
C 10%
...Expand
(8S,9R)-cinchonane-9,6'-diol

(8S,9R)-cinchonane-9,6'-diol

Cinchonidin
485-71-2

Cinchonidin

Conditions
ConditionsYield
ueber mehrere Stufen;
Cinchonin
118-10-5

Cinchonin

pentylalcoholic KOH-solution

pentylalcoholic KOH-solution

Cinchonidin
485-71-2

Cinchonidin

pentan-1-ol
71-41-0

pentan-1-ol

Cinchonin
118-10-5

Cinchonin

KOH

KOH

A

(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane
118-10-5, 485-70-1, 485-71-2, 550-54-9, 40134-63-2, 72402-55-2, 72402-56-3

(1S,3R,4S,8S,9S)-9-hydroxy-cinchonane

B

Cinchonidin
485-71-2

Cinchonidin

C

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

(+)-cinchonine

Conditions
ConditionsYield
Product distribution;
...Expand
Cinchonin
118-10-5

Cinchonin

A

Cinchonidin
485-71-2

Cinchonidin

B

epicinchonin; epicinchonidine

epicinchonin; epicinchonidine

Conditions
ConditionsYield
With potassium hydroxide; pentan-1-ol
methyllithium
917-54-4

methyllithium

Cinchonidin
485-71-2

Cinchonidin

2'-methylcinchonidine

2'-methylcinchonidine

Conditions
ConditionsYield
In tetrahydrofuran at -10 - 20℃; for 5h; Inert atmosphere;100%
In tetrahydrofuran at -10 - 50℃; for 6h; Inert atmosphere; Schlenk technique;100%
In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere;14%
In tetrahydrofuran at -78.16℃; for 12h; Inert atmosphere;14%
benzyl chloride
100-44-7

benzyl chloride

Cinchonidin
485-71-2

Cinchonidin

(8S,9R)-(-)-N-benzylcinchonidinium chloride
69221-14-3, 69257-04-1, 95189-65-4

(8S,9R)-(-)-N-benzylcinchonidinium chloride

Conditions
ConditionsYield
In toluene for 2h; Reflux;100%
With sodium iodide In tetrahydrofuran at 20℃; Reflux;
3,5-bistrifluoromethylphenylisothiocyanate
23165-29-9

3,5-bistrifluoromethylphenylisothiocyanate

Cinchonidin
485-71-2

Cinchonidin

O-((R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)(3,5-bis(trifluoromethyl)phenyl)carbamothioate

O-((R)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)(3,5-bis(trifluoromethyl)phenyl)carbamothioate

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;99%
2-{3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy}acetic acid
215169-00-9

2-{3-[(1R)-3-(3,4-dimethoxyphenyl)-1-hydroxypropyl]phenoxy}acetic acid

Cinchonidin
485-71-2

Cinchonidin

C19H22N2O*C19H22O6

C19H22N2O*C19H22O6

Conditions
ConditionsYield
In ethyl acetate at 50℃; for 1h;99%
Cinchonidin
485-71-2

Cinchonidin

methyl iodide
74-88-4

methyl iodide

O-methoxycinchonidine

O-methoxycinchonidine

Conditions
ConditionsYield
Stage #1: Cinchonidin 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;		98%
With sodium hydride In N,N-dimethyl-formamide at 0 - 50℃; for 2.5h;46%
Stage #1: Cinchonidin With sodium hydride In tetrahydrofuran; mineral oil at 0 - 50℃; for 1.5h; Inert atmosphere; Schlenk technique;
Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 72h; Inert atmosphere; Schlenk technique;		1%
N2-acetyl-2,O4-dimethyltyrosine
96574-31-1

N2-acetyl-2,O4-dimethyltyrosine

Cinchonidin
485-71-2

Cinchonidin

(R)-Quinolin-4-yl-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; compound with 2-acetylamino-3-(4-methoxy-phenyl)-2-methyl-propionic acid

(R)-Quinolin-4-yl-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; compound with 2-acetylamino-3-(4-methoxy-phenyl)-2-methyl-propionic acid

Conditions
ConditionsYield
97.4%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Cinchonidin
485-71-2

Cinchonidin

4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-quinoline
183994-23-2

4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-quinoline

Conditions
ConditionsYield
With dmap; triethylamine In N,N-dimethyl-formamide for 24h; Ambient temperature;97%
Cinchonidin
485-71-2

Cinchonidin

4-(bromomethyl)-N-tert-butylbenzenesulfonamide
415679-05-9

4-(bromomethyl)-N-tert-butylbenzenesulfonamide

C30H38N3O3S(1+)*Br(1-)

C30H38N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In methanol at 40℃; for 15h;97%
C14H14BrNO2S

C14H14BrNO2S

Cinchonidin
485-71-2

Cinchonidin

C33H36N3O3S(1+)*Br(1-)

C33H36N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In methanol at 40℃; for 15h;97%
C14H14BrNO3S

C14H14BrNO3S

Cinchonidin
485-71-2

Cinchonidin

C33H36N3O4S(1+)*Br(1-)

C33H36N3O4S(1+)*Br(1-)

Conditions
ConditionsYield
In methanol at 25℃; for 20h;97%
Cinchonidin
485-71-2

Cinchonidin

1,3-bis-(bromomethyl)benzene
626-15-3

1,3-bis-(bromomethyl)benzene

α,α'-biscinchonidinium-m-xylene dibromide

α,α'-biscinchonidinium-m-xylene dibromide

Conditions
ConditionsYield
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃; for 6h;96%
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃; for 4h;72%
In ethanol; chloroform; N,N-dimethyl-formamide
Cinchonidin
485-71-2

Cinchonidin

1,3-bis-(bromomethyl)benzene
626-15-3

1,3-bis-(bromomethyl)benzene

C46H52N4O2(2+)*2Br(1-)

C46H52N4O2(2+)*2Br(1-)

Conditions
ConditionsYield
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃; for 6h;96%
iodomethylbenzene
620-05-3

iodomethylbenzene

Cinchonidin
485-71-2

Cinchonidin

C26H29N2O(1+)*I(1-)

C26H29N2O(1+)*I(1-)

Conditions
ConditionsYield
In tetrahydrofuran for 12h; Inert atmosphere; Reflux;96%
1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

Cinchonidin
485-71-2

Cinchonidin

(2S,4S,5R)-2-((R)-hydroxy(quinolin-4-yl)methyl)-1-(4-nitrobenzyl)-5-vinylquinuclidin-1-ium bromide
123355-59-9

(2S,4S,5R)-2-((R)-hydroxy(quinolin-4-yl)methyl)-1-(4-nitrobenzyl)-5-vinylquinuclidin-1-ium bromide

Conditions
ConditionsYield
In tetrahydrofuran Reflux;95%
In acetonitrile Inert atmosphere;83%
In tetrahydrofuran for 4h; Heating;
2-(bromomethyl)naphthalene
3163-27-7

2-(bromomethyl)naphthalene

Cinchonidin
485-71-2

Cinchonidin

(2S,4S,5R)-2-((R)-hydroxy(quinolin-4-yl)methyl)-1-(naphthalen-1-ylmethyl)-5-vinylquinuclidin-1-ium bromide

(2S,4S,5R)-2-((R)-hydroxy(quinolin-4-yl)methyl)-1-(naphthalen-1-ylmethyl)-5-vinylquinuclidin-1-ium bromide

Conditions
ConditionsYield
In acetonitrile Inert atmosphere;95%
In tetrahydrofuran Reflux;80%
chloromethyldiphenylsilane
144-79-6

chloromethyldiphenylsilane

Cinchonidin
485-71-2

Cinchonidin

cinchonidine diphenylmethylsilyl ether

cinchonidine diphenylmethylsilyl ether

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;95%
C13H11BrINO2S

C13H11BrINO2S

Cinchonidin
485-71-2

Cinchonidin

C32H33IN3O3S(1+)*Br(1-)

C32H33IN3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 20h;94%
C11H16BrNO2S

C11H16BrNO2S

Cinchonidin
485-71-2

Cinchonidin

C30H38N3O3S(1+)*Br(1-)

C30H38N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 20h;94%
C17H14BrNO2S

C17H14BrNO2S

Cinchonidin
485-71-2

Cinchonidin

C36H36N3O3S(1+)*Br(1-)

C36H36N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In methanol at 40℃; for 18h;94%
C14H14BrNO2S

C14H14BrNO2S

Cinchonidin
485-71-2

Cinchonidin

C33H36N3O3S(1+)*Br(1-)

C33H36N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 20h;94%
Cinchonidin
485-71-2

Cinchonidin

C19H21BrN2O

C19H21BrN2O

Conditions
ConditionsYield
With bromine; triethylamine In chloroform at 0 - 20℃; for 4h;94%
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

Cinchonidin
485-71-2

Cinchonidin

(1S,2S,4S,5R)-1-(4-Fluoro-benzyl)-2-((R)-hydroxy-quinolin-4-yl-methyl)-5-vinyl-1-azonia-bicyclo[2.2.2]octane; bromide

(1S,2S,4S,5R)-1-(4-Fluoro-benzyl)-2-((R)-hydroxy-quinolin-4-yl-methyl)-5-vinyl-1-azonia-bicyclo[2.2.2]octane; bromide

Conditions
ConditionsYield
In tetrahydrofuran Reflux;93%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Cinchonidin
485-71-2

Cinchonidin

9-O-mesyl cinchonidine

9-O-mesyl cinchonidine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h;93%
Cinchonidin
485-71-2

Cinchonidin

(-)-hydrocinchonidine
485-64-3

(-)-hydrocinchonidine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 10h;92%
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 12h;86%
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 24h; Reagent/catalyst; Green chemistry; chemoselective reaction;83%
4-(bromomethyl)phenyl[di(1-naphthyl)]methanol
861815-63-6

4-(bromomethyl)phenyl[di(1-naphthyl)]methanol

Cinchonidin
485-71-2

Cinchonidin

1-[4-{hydroxydiphenylmethyl}benzyl]cinchonidinium bromide

1-[4-{hydroxydiphenylmethyl}benzyl]cinchonidinium bromide

Conditions
ConditionsYield
In toluene; acetonitrile at 80℃; for 6h;92%
4-(bromomethyl)-N-(phenyl)benzenesulfonamide
1308718-76-4

4-(bromomethyl)-N-(phenyl)benzenesulfonamide

Cinchonidin
485-71-2

Cinchonidin

C32H34N3O3S(1+)*Br(1-)

C32H34N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; for 20h;92%
1-(bromomethyl)-2,3,4-trifluorobenzene

1-(bromomethyl)-2,3,4-trifluorobenzene

Cinchonidin
485-71-2

Cinchonidin

N-(2',3',4'-trifluoro)benzylhydrocinchonidinium bromide

N-(2',3',4'-trifluoro)benzylhydrocinchonidinium bromide

Conditions
ConditionsYield
In ethanol; chloroform; N,N-dimethyl-formamide at 100℃; for 4h;91%
In tetrahydrofuran for 4h; Heating;
5-(bromomethyl)-1,3-di-tert-butyl-2-methoxybenzene
93629-15-3

5-(bromomethyl)-1,3-di-tert-butyl-2-methoxybenzene

Cinchonidin
485-71-2

Cinchonidin

N-(4-methoxy-3,5-di-tert-butylbenzyl)cinchonidinium bromide

N-(4-methoxy-3,5-di-tert-butylbenzyl)cinchonidinium bromide

Conditions
ConditionsYield
In toluene for 4h; Heating;91%
C13H9BrF3NO2S

C13H9BrF3NO2S

Cinchonidin
485-71-2

Cinchonidin

C32H31F3N3O3S(1+)*Br(1-)

C32H31F3N3O3S(1+)*Br(1-)

Conditions
ConditionsYield
In methanol at 40℃; for 15h;90%
4-Methylbenzyl bromide
104-81-4

4-Methylbenzyl bromide

Cinchonidin
485-71-2

Cinchonidin

(3ξ,8α,9R)-9-hydroxy-1-(4-methylbenzyl)cinchonan-1-ium bromide

(3ξ,8α,9R)-9-hydroxy-1-(4-methylbenzyl)cinchonan-1-ium bromide

Conditions
ConditionsYield
In tetrahydrofuran Reflux;90%

Cinchonidine Consensus Reports

Reported in EPA TSCA Inventory.

Cinchonidine Specification

The Cinchonidine, with the CAS registry number 485-71-2, is also known as (8S,9R)-Cinchonidine. It belongs to the product categories of Cyclic compounds; Alkaloids; Chiral; Biochemistry; Optical Resolution; Quinoline Alkaloids; Quinoline carboxylic Acids, etc.; Quinolines; Synthetic Organic Chemistry; Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 207-622-3. This chemical's molecular formula is C19H22N2O and molecular weight is 294.39. What's more, its systematic name is (8α,9R)-Cinchonan-9-ol. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Natural Product. This chemical is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonine. This chemcial should be sealed and stored in a ventilated and dry place. Moreover, it should be protected from oxides.

Physical properties of Cinchonidine are: (1)ACD/LogP: 2.788; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.29; (4)ACD/LogD (pH 7.4): 0.90; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 10.06; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 36.36 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 89.424 cm3; (15)Molar Volume: 244.537 cm3; (16)Polarizability: 35.45×10-24cm3; (17)Surface Tension: 56.4 dyne/cm; (18)Density: 1.204 g/cm3; (19)Flash Point: 234.723 °C; (20)Enthalpy of Vaporization: 76.485 kJ/mol; (21)Boiling Point: 464.502 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of Cinchonidine: it can be used to produce N-(p-bromobenzyl)-cinchonidinium bromide at the ambient temperature. It will need solvent CH2Cl2 with the reaction time of 17 hours. The yield is about 65%.

Cinchonidine can be used to produce N-(p-bromobenzyl)-cinchonidinium bromide at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemcial is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. This substance may cause sensitisation by inhalation and skin contact. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. You should not breathe dust. When using it, you need wear suitable protective clothing and gloves and you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: n2c1c(cccc1)c(cc2)[C@@H](O)[C@H]3N4CC[C@@H](C3)[C@@H](/C=C)C4
(2)Std. InChI: InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18-,19+/m0/s1
(3)Std. InChIKey: KMPWYEUPVWOPIM-KODHJQJWSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.
rat LD50 intraperitoneal 206mg/kg (206mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Acta Pharmacologica et Toxicologica. Vol. 4, Pg. 265, 1948.

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