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Merck

134910

(1R,2S)-(−)-Ephedrine

98%

Synonym(s):

(−)-Ephedrine, (1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (1R,2S)-(−)-2-Methylamino-1-phenyl-1-propanol, L-α-(1-Methylaminoethyl)benzyl alcohol

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About This Item

Linear Formula:
C6H5CH[CH(NHCH3)CH3]OH
CAS Number:
299-42-3
Molecular Weight:
165.23
UNSPSC Code:
12352116
NACRES:
NA.22
PubChem Substance ID:
24848190
EC Number:
206-080-5
Beilstein/REAXYS Number:
2208730
MDL number:
MFCD00064257

Key Documents

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Product Name

(1R,2S)-(−)-Ephedrine, 98%

InChI key

KWGRBVOPPLSCSI-WPRPVWTQSA-N

InChI

1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

SMILES string

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

assay

98%

form

solid

optical activity

[α]21/D −41°, c = 5 in 1 M HCl

bp

255 °C (lit.)

mp

37-39 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

functional group

amine
hydroxyl
phenyl

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

(1R,2S)-(-)-Ephedrine can be used in the preparation of optically active phosphine-phosphonite ligands and chirally-substituted cyclopentadienyl (Cp) ligands. It reacts with phosphorus trichloride to form (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine. It can also act as a chiral resolving agent for (±)-mandelic acid.
Versatile chiral synthon, employed in catalysis and in the preparation of optically pure sulfoxides and oxazolidines.

General description

(1R,2S)-(-)-Ephedrine, a chiral β-amino alcohol, is commonly used as a chiral auxiliary in asymmetric synthesis. It undergoes reduction to form (+)-methamphetamine.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 1

flash_point_f

186.8 °F - closed cup

flash_point_c

86 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7974
STBG4818V
STBG2435V
STBF3993V
STBF0862V

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Synthetic Communications, 829-829 (1992)
A novel chiral cyclopentadienyl ligand based on ephedrine
van der Zeijden AAH
Tetrahedron Asymmetry, 6(4), 913-918 (1995)
Penelope P Howards et al.
PloS one, 7(11), e50372-e50372 (2012-11-21)
Medications may be consumed periconceptionally before a woman knows she is pregnant. In this study, the authors evaluate the association of a prescription diet drug (Letigen) containing ephedrine (20 mg) and caffeine (200 mg) with spontaneous abortion (SAB) in the
Investigation of (1R, 2S)-(-)-Ephedrine by Cryogenic Terahertz Spectroscopy and Solid-State Density Functional Theory.
Hakey PM, et al
ChemPhysChem, 10(14), 2434-2444 (2009)
Tetrahedron Asymmetry, 2, 1123-1123 (1991)
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