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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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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

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.

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.

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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A L Carey et al.
Diabetologia, 56(1), 147-155 (2012-10-16)
Brown adipose tissue (BAT) activation increases energy consumption and may help in the treatment of obesity. Cold exposure is the main physiological stimulus for BAT thermogenesis and the sympathetic nervous system, which innervates BAT, is essential in this process. However
A novel nucleoside phosphoramidite synthon derived from 1R, 2S-ephedrine
Iyer RP, et al
Tetrahedron Asymmetry, 6(5), 1051-1054 (1995)
Tetrahedron Asymmetry, 2, 1123-1123 (1991)
Synthetic Communications, 829-829 (1992)
A novel chiral cyclopentadienyl ligand based on ephedrine
van der Zeijden AAH
Tetrahedron Asymmetry, 6(4), 913-918 (1995)
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