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525863

Sigma-Aldrich

trans-2-Aminocyclopentanol hydrochloride

97%

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About This Item

Empirical Formula (Hill Notation):
C5H11NO · HCl
CAS Number:
Molecular Weight:
137.61
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

mp

191-196 °C (lit.)

SMILES string

Cl.N[C@H]1CCC[C@@H]1O

InChI

1S/C5H11NO.ClH/c6-4-2-1-3-5(4)7;/h4-5,7H,1-3,6H2;1H/t4-,5-;/m0./s1

InChI key

ZFSXKSSWYSZPGQ-FHAQVOQBSA-N

General description

trans-2-Aminocyclopentanol hydrochloride is an aminocyclanol. Its d,l-cis- and d,l-trans- forms have been synthesized. The trans-form of the product can be produced in large (multigram) scale via carbamate addition protocol. Cholinesterase inhibitory potential of cis-form of 2-aminocyclopentanol hydrochloride is higher (twofold) that of its trans-form.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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Stereochemistry of Aminocyclanols. Synthesis of cis Epimers via Oxazolines. The 2-Aminocyclopentanols*.
McCasland GE and Smith DA.
Journal of the American Chemical Society, 72(5), 2190-2195 (1950)
James A Birrell et al.
Organic letters, 15(12), 2895-2897 (2013-06-08)
A highly enantioselective addition of phenyl carbamate to meso-epoxides has been developed to efficiently generate protected trans-1,2-amino alcohols. This transformation is promoted by an oligomeric (salen)Co-OTf catalyst and has been used to prepare two useful 2-aminocycloalkanol hydrochlorides in enantiopure form
Preparation of antidotes for anticholinesterase poisoning. IV. Synthesis and protective effectiveness of 2'-(cis-and trans-2'-hydroxycyclohexyl) aminoethyl 1-phenylcyclopentanecarboxylate hydrochlorides.
Bannard RAB and Parkkari JH.
Canadian Journal of Chemistry, 48(9), 1377-1382 (1970)

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