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134910 Sigma-Aldrich

(1R,2S)-(−)-Ephedrine

98%

Synonym: (−)-Ephedrine, (1R,2S)-(−)-α-(1-Methylaminoethyl)benzyl alcohol, (1R,2S)-(−)-2-Methylamino-1-phenyl-1-propanol, L-α-(1-Methylaminoethyl)benzyl alcohol

  • CAS Number 299-42-3

  • Linear Formula C6H5CH[CH(NHCH3)CH3]OH

  • Molecular Weight 165.23

  •  Beilstein/REAXYS Number 2208730

  •  EC Number 206-080-5

  •  MDL number MFCD00064257

  •  PubChem Substance ID 24848190

  •  NACRES NA.22

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Properties

Related Categories Alkaloid, Asymmetric Synthesis, Cell Biology, Chemical Synthesis, Chiral Auxiliaries,
Quality Level   200
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

Description

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
KB0700000
Flash Point(F) 
186.8 °F - closed cup
Flash Point(C) 
86 °C - closed cup
Protocols & Articles

Articles

Ephedrines

Both enantiomers of ephedrine, pseudoephedrine, norephedrine, and their derivatives are used as practical chiral auxiliaries for asymmetric synthesis. Enolates of readily available (1R,2R)-(–)- and (...
Aldrich ChemFiles 2005, 5.4, 9.
Keywords: Alkylations, Asymmetric synthesis, Chemfiles, Chiral auxiliaries

HPLC Analysis of Ephedrine Enantiomers on CHIRALPAK® AGP

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Ephedrine Enantiomers on CHIRALPAK® AGP
Keywords: Chromatography, High performance liquid chromatography, Pharmaceutical

Peer-Reviewed Papers
15

References

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