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378704

Sigma-Aldrich

Tropane

98%

Synonym(s):

8-Methyl-8-azabicyclo[3.2.1]octane

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About This Item

Empirical Formula (Hill Notation):
C8H15N
CAS Number:
Molecular Weight:
125.21
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
Assay:
98%
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Assay

98%

form

liquid

refractive index

n20/D 1.477 (lit.)

bp

167-169 °C (lit.)

density

0.931 g/mL at 25 °C (lit.)

SMILES string

CN1[C@H]2CCC[C@@H]1CC2

InChI

1S/C8H15N/c1-9-7-3-2-4-8(9)6-5-7/h7-8H,2-6H2,1H3/t7-,8+

InChI key

XLRPYZSEQKXZAA-OCAPTIKFSA-N

General description

Tropane (8-methyl-8-azabicyclo[3.2.1]-octane) is a bridged bicyclic N-containing compound.[1] The 8-methyl-8-azabicyclo[3.2.1]-octane has a tropane ring system, which is an important substructure in a number of natural products and synthetic compounds of biological and medicinal importance.[2] Production of tropane alkaloid in callus and root cultures of seven Hyoscyamus species has been studied.[3] Tropane derivatives are reported to undergo rapid N-methyl inversion.[4]

Pictograms

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Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

107.6 °F - closed cup

Flash Point(C)

42 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Enhancing Tropane Alkaloid Production Based on the Functional Identification of Tropine-Forming Reductase in
Kaihui Zhao et al.
Frontiers in plant science, 8, 1745-1745 (2017-11-01)
A Kokotkiewicz et al.
Food chemistry, 221, 535-540 (2016-12-17)
Thin layer chromatographic methods for quantitative determination of nightshade-specific tropane (l-hyoscyamine, scopolamine) and steroidal alkaloids (α-solanine, α-chaconine) in goji berries (L. barbarum L., Solanaceae) were developed. The analysis of tropane derivatives included separation on silica gel-coated HPTLC plates using mobile
Determination of the N-methyl stereochemistry in tropane and granatane derivatives in solution: a computational and NMR spectroscopic study.
Lazny R, et al.
Tetrahedron, 68(31), 6158-6163 (2012)
An improved synthesis of (+)-2-tropinone.
Zhang C, et al.
The Journal of Organic Chemistry, 62(22), 7888-7889 (1997)
Lu Wang et al.
Angewandte Chemie (International ed. in English), 53(22), 5657-5661 (2014-04-18)
A palladium-catalyzed oxidative carbonylative esterification of a variety of functionalized alcohols under base- and ligand-free conditions has been demonstrated. A CO/olefin combination was utilized as the acylating reagent with O2 as a benign oxidant. Notably, the scope of the substrate

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