Cinchonidine

Cinchonidine Basic information

Product Name:	Cinchonidine
Synonyms:	(8-alpha,9r)-cinchonan-9-o;(8alpha,9theta)-cinchonan-9-o;(8s,9r)-cinchonidine;2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-;Cinchonan-9-ol;Cinchonan-9-ol, (8alpha,9R)-;Cinchovatine;Cinchonidinederivedcatalyst
CAS:	485-71-2
MF:	C19H22N2O
MW:	294.39
EINECS:	207-622-3
Product Categories:	AMEBARSONE;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids;chiral;Biochemistry;for Resolution of Acids;Optical Resolution;Quinoline Alkaloids;Quinolinecarboxylic Acids, etc.;Quinolines;cyclic compounds;Synthetic Organic Chemistry
Mol File:	485-71-2.mol

Cinchonidine Chemical Properties

Melting point	204-206 °C(lit.)
alpha	-115 º (c=1, EtOH)
Boiling point	436.16°C (rough estimate)
density	1.0863 (rough estimate)
vapor pressure	0Pa at 25℃
refractive index	-107.5 ° (C=1, EtOH)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	0.25g/l
pka	5.80, 10.03(at 25℃)
form	Crystalline Powder
color	White to cream
PH	9 (0.2g/l, H2O, 20℃)
optical activity	[α]23/D 109.2°, c = 1.5 in ethanol
Water Solubility	Insoluble
Sensitive	Light Sensitive
Merck	14,2286
BRN	89690
Stability:	Stable, but light-sensitive. Incompatible with strong oxidizing agents.
InChIKey	KMPWYEUPVWOPIM-NAHPKXJFSA-N
LogP	2.68 at 25℃
CAS DataBase Reference	485-71-2(CAS DataBase Reference)
NIST Chemistry Reference	Cinchonidine(485-71-2)
EPA Substance Registry System	Cinchonan-9-ol, (8.alpha.,9R)- (485-71-2)

Safety Information

Hazard Codes	Xn,Xi
Risk Statements	20/21/22-42/43-36/37/38-20/22-48/22-43-22-63
Safety Statements	22-24/25-36/37-36-26
RIDADR	1544
WGK Germany	3
RTECS	GD2975000
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29392900
Toxicity	LD50 i.p. in rats: 206 mg/kg (Johnson, Poe); LD50 orally in quail: >316 mg/kg (Schafer)

MSDS Information

Provider	Language
L-Cinchonidine	English
ACROS	English
SigmaAldrich	English
ALFA	English

Cinchonidine Usage And Synthesis

Chemical Properties	white to light yellow crystal powde
Uses	antiamebic, antiprotozoal
Uses	Cinchonidine occurs in most varieties of Cinchona bark and is stereoisomeric with Cinchonine. Cinchonidine exhibits Antimalarial properties.
Definition	ChEBI: 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.
Flammability and Explosibility	Nonflammable
Purification Methods	Crystallise cinchonidine from aqueous EtOH. For the N-benzylcinchonidinium chloride see above entry in this section. [Beilstein 23 III/IV 2824.]

Cinchonidine Preparation Products And Raw materials

Preparation Products

(S)-(-)-7,7'-BIS[DI(3,5-DIMETHYLPHENYL)PHOSPHINO]-2,2',3,3'-TETRAHYDRO-1,1'-SPIROBIINDANE-->(R)-7,7'-BIS(DIPHENYLPHOSPHINO)-1,1'-SPIROBIINDANE-->(S)-1,1'-SPIROBIINDANE-7,7'-DIOL-->(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE-->(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-PHENOXY-->(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-DIMETHYLAMINE-->1,1'-SPIROBIINDANE-7,7'-DIOL-->1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,-->1,1'-BIS(DI-TERT-BUTYLPHOSPHINO)FERROCENE-->2-(Dicyclohexylphosphino)biphenyl-->Esfenvalerate-->QUININE SULFATE-->Fosinopril-->Benazepril-->N-Benzylcinchonidinium chloride

QUININE PHOSPHATE QUININE GLUCONATE QUININE CITRATE Clothianidin QUININE ACETATE 4-Methoxyphenylacetone Anisole 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE Cinchonidine QUININE LACTATE QUININE VALERATE p-Anisidine Silicone rubber,methyl-vinyl Vinyl resin Quinidine QUININE GLYCEROPHOSPHATE 3-Methoxybenzaldehyde Diethylstilbestrol

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