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134910

Sigma-Aldrich

(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:
Molecular Weight:
165.23
Beilstein/REAXYS Number:
2208730
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22

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Quality Level

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

SMILES string

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

General description

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

Application

(1R,2S)-(-)-Ephedrine can be used in the preparation of optically active phosphine-phosphonite ligands[3] and chirally-substituted cyclopentadienyl (Cp) ligands.[4] It reacts with phosphorus trichloride to form (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine.[5] It can also act as a chiral resolving agent for (±)-mandelic acid.[6]
Versatile chiral synthon,[7] employed in catalysis[8] and in the preparation of optically pure sulfoxides[9] and oxazolidines.[10]

pictograms

CorrosionExclamation mark

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_germany

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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