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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:
299-42-3
Molecular Weight:
165.23
Beilstein:
2208730
EC Number:
206-080-5
MDL number:
MFCD00064257
UNSPSC Code:
12352116
PubChem Substance ID:
24848190
NACRES:
NA.22

Quality Level

200

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

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

Signal Word

Danger

Hazard Statements

H302,H314,H317

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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(1S,2R)-(+)-Ephedrine hydrochloride 1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material, Cerilliant®

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E-011

(1S,2R)-(+)-Ephedrine hydrochloride

Synthetic Communications, 829-829 (1992)
A novel chiral cyclopentadienyl ligand based on ephedrine
van der Zeijden AAH
Tetrahedron Asymmetry, 6(4), 913-918 (1995)
Tetrahedron Asymmetry, 2, 1123-1123 (1991)
Penelope P Howards et al.
PloS one, 7(11), e50372-e50372 (2012-11-21)
Medications may be consumed periconceptionally before a woman knows she is pregnant. In this study, the authors evaluate the association of a prescription diet drug (Letigen) containing ephedrine (20 mg) and caffeine (200 mg) with spontaneous abortion (SAB) in the
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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