134910

Sigma-Aldrich

(1R,2S)-(−)-Ephedrine

98%

Synonym(s):
(1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (−)-Ephedrine, (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/REAXYS Number:
2208730
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

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

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.

Packaging

25, 100 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 1

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

A novel chiral cyclopentadienyl ligand based on ephedrine
van der Zeijden AAH
Tetrahedron Asymmetry, 6(4), 913-918 (1995)
Synthetic Communications, 829-829 (1992)
Tetrahedron Asymmetry, 2, 1123-1123 (1991)
(1R,2S)-Ephedrine
Soai K and Hitchcock SR
e-EROS Encyclopedia of Reagents for Organic Synthesis. null
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)

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