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472549

Sigma-Aldrich

(2R,5R)-(+)-5-Vinyl-2-quinuclidinemethanol

96%

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Empirical Formula (Hill Notation):
C10H17NO
Molecular Weight:
167.25
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

96%

optical activity

[α]20/D +189°, c = 1 in methanol

refractive index

n20/D 1.515 (lit.)

bp

267 °C (lit.)

density

1.073 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OC[C@H]1CC2CCN1C[C@@H]2C=C

InChI

1S/C10H17NO/c1-2-8-6-11-4-3-9(8)5-10(11)7-12/h2,8-10,12H,1,3-7H2/t8-,9+,10+/m0/s1

InChI key

GAFZBOMPQVRGKU-IVZWLZJFSA-N

Application

Valuable building block for medicinal chemistry. The skeleton of this compound is identical to the framework of cinchona alkaloids. Possible applications include resolving agents, chiral stationary phases, and chiral ligands in asymmetric synthesis.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Regulatory Information

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S S Hong et al.
Chirality, 4(7), 432-438 (1992-01-01)
Recently we synthesized a naphthalene analog of medetomidine, 4-[1-(1-naphthyl)ethyl]-1H-imidazole hydrochloride (1), and found it to be highly potent in adrenergic systems. The separation of optical isomers of this naphthalene analog was achieved by using the isomers of tartaric acid. The
Ojima, I., ed.
Catalytic Asymmetric Synthesis (1993)

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