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

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

hazcat

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

storage_class_code

8A - Combustible, corrosive hazardous materials

WGK Germany

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

Certificate of Analysis

Certificate of Origin

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 Letters, 32, 5885-5885 (1991)
Enantiomeric Resolution of (?)-Mandelic Acid by (1R, 2S)-(-)-Ephedrine. An Organic Chemistry Laboratory Experiment Illustrating Stereoisomerism
Baar MR and Cerrone-Szakal AL
Journal of Chemical Education, 82(7), 1040-1040 (2005)
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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