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Sigma-Aldrich

(1R,2S)-(−)-Ephedrine

98%

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Synonym(s):
(−)-Ephedrine, (1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (1R,2S)-(−)-2-Methylamino-1-phenyl-1-propanol, L-α-(1-Methylaminoethyl)benzyl alcohol
Linear Formula:
C6H5CH[CH(NHCH3)CH3]OH
CAS Number:
Molecular Weight:
165.23
Beilstein:
2208730
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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.)

storage temp.

2-8°C

SMILES string

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

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

InChI key

KWGRBVOPPLSCSI-WPRPVWTQSA-N

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This Item
317500235210862231
form

solid

form

solid

form

solid

form

crystals

optical activity

[α]21/D −41°, c = 5 in 1 M HCl

optical activity

[α]20/D +40°, c = 7 in 1 M HCl

optical activity

[α]21/D −29.2°, c = 5 in methanol

optical activity

[α]20/D −34°, c = 4 in H2O

bp

255 °C (lit.)

bp

-

bp

-

bp

-

mp

37-39 °C (lit.)

mp

51-54 °C (lit.)

mp

86-88 °C (lit.)

mp

216-220 °C (lit.)

density

1.124 g/mL at 25 °C (lit.)

density

-

density

-

density

-

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A novel chiral cyclopentadienyl ligand based on ephedrine
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