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317500

Sigma-Aldrich

(1S,2R)-(+)-Norephedrine

98%

Sinónimos:

(1S,2R)-2-Amino-1-phenyl-1-propanol, erythro-α-(1-aminoethyl)benzyl alcohol, D-(+)-Norephedrine, Phenylpropanolamine

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About This Item

Fórmula lineal:
C6H5CH(OH)CH(CH3)NH2
Número de CAS:
37577-28-9
Peso molecular:
151.21
Beilstein/REAXYS Number:
2802896
MDL number:
MFCD00064411
UNSPSC Code:
12352116
PubChem Substance ID:
24859081
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

optical activity

[α]20/D +40°, c = 7 in 1 M HCl

mp

51-54 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@@H](N)[C@@H](O)c1ccccc1

InChI

1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1

InChI key

DLNKOYKMWOXYQA-VXNVDRBHSA-N

Categorías relacionadas

General description

(1S,2R)-(+)-Norephedrine is an enantiomer of ephedrine mainly used as a chiral auxiliary for asymmetric synthesis.

Application

(1S,2R)-(+)-Norephedrine may be used in the preparation of dendritic ligands, which on combining with Ru(II) complexes form efficient asymmetric transfer hydrogenation catalysts. It may also be used in the preparation of N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)furan-2-carboxamide. This chiral amide can efficiently catalyze the enantioselective ethylation of aromatic and heteroaromatic aldehydes to secondary alcohols in the absence of titanium tetraisopropoxide as promotor.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

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Chiral amide from (1S, 2R)-(+)-norephedrine alkaloid in the enantioselective addition of diethylzinc to aryl and heteroaryl aldehydes.
Ananthi N, et al.
Tetrahedron Asymmetry, 20(15), 1731-1735 (2009)
Dendritic catalysts for asymmetric transfer hydrogenation based (1S, 2R)-norephedrine derived ligands.
Liu PN, et al.
Tetrahedron Asymmetry, 14(16), 2481-2485 (2003)
Ana Caroline Costa Sa et al.
Scientific reports, 9(1), 8795-8795 (2019-06-21)
Growing evidence suggests that peripheral factors to the brain driving neuro-inflammation could affect Alzheimer's Disease (AD) and Parkinson's Disease (PD) severity. Herpes simplex virus type 1 (HSV1) infection has been associated with AD while other related viruses, including cytomegalovirus (CMV)
Stefan W Toennes et al.
Journal of pharmaceutical and biomedical analysis, 179, 113008-113008 (2019-12-02)
Each year, synthetic drugs are occurring in high numbers in the illicit drug market. But data on their pharmacology and toxicology are scarcely available. Therefore, a pilot study was performed to evaluate excretion of 4-fluoroamphetamine (4FA) in humans and identify
María José Ojeda-Montes et al.
Future medicinal chemistry, 9(18), 2129-2146 (2017-11-28)
Extracts from Ephedra species have been reported to be effective as antidiabetics. A previous in silico study predicted that ephedrine and five ephedrine derivatives could contribute to the described antidiabetic effect of Ephedra extracts by inhibiting dipeptidyl peptidase IV (DPP-IV).
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Chromatograms

application for HPLC

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