134910

(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
• 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

Properties

• 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

Description

General description

(1R,2S)-(-)-Ephedrine, a chiral β-amino alcohol, is commonly used as a chiral auxiliary in asymmetric synthesis.[1] It undergoes reduction to form (+)-methamphetamine.[2]

Application

(1R,2S)-(-)-Ephedrine can be used in the preparation of optically active phosphine-phosphonite ligands[3] and chirally-substituted cyclopentadienyl (Cp) ligands.[4] It reacts with phosphorus trichloride to form (2R,4S,5R)-2-chloro-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine.[5] It can also act as a chiral resolving agent for (±)-mandelic acid.[6]

Versatile chiral synthon,[7] employed in catalysis[8] and in the preparation of optically pure sulfoxides[9] and oxazolidines.[10]

Safety Information

• Pictograms: GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H302 - H314 - H317
• Precautionary Statements: P260 - P272 - P280 - P301 + P312 - P303 + P361 + P353 - P305 + P351 + P338
• 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