(1S,2R)-2-(dimethylamino)-1-phenylpropan-1-ol

• ChemBase ID: 148987
• Molecular Formular: C11H17NO
• Molecular Mass: 179.25878
• Monoisotopic Mass: 179.13101417
• SMILES: C[C@H]([C@H](c1ccccc1)O)N(C)C
• Canonical SMILES: O[C@H]([C@H](N(C)C)C)c1ccccc1
• InChI: InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m1/s1
• InChIKey: FMCGSUUBYTWNDP-MWLCHTKSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R)-2-(dimethylamino)-1-phenylpropan-1-ol
• IUPAC Traditional name: (1S,2R)-2-(dimethylamino)-1-phenylpropan-1-ol
• Synonyms: (1S,2R)-(+)-2-Dimethylamino-1-phenylpropanol; (+)-N-Methylephedrine; (+)-(1S,2R)-2-Dimethylamino-1-phenylpropanol; (+)-N-Methylephedrine; (1S,2R)-(+)-N-Methylephedrine; (1S,2R)-(+)-2-二甲基氨基-1-苯丙醇; (+)-N-甲基麻黄碱; (+)-(1S,2R)-2-二甲基氨基-1-苯丙醇; (+)-N-甲基麻黄碱; (1S,2R)-(+)-N-甲基麻黄碱

Database IDs

• CAS Number: 42151-56-4
• MDL Number: MFCD00064259
• Beilstein Number: 3198945
• PubChem SID: 24885008; 162243157; 24857291
• PubChem CID: 102023

CALCULATED PROPERTIES

• Acid pKa: 13.882206
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.4248142
• LogD (pH = 7.4): 0.22741346
• Log P: 1.7008827
• Molar Refractivity: 54.982 cm^3
• Polarizability: 21.698908 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 86-88 °C; 87-90 °C(lit.)
• Optical Rotation: [α]20/D +29°, c = 5 in methanol; [α]20/D +30±2°, c = 4.5% in methanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (NT); 99%
• Grade: purum
• Linear Formula: C6H5CH(OH)CH(CH3)N(CH3)2
• Empirical Formula (Hill Notation): C11H17NO

DETAILS

Sigma Aldrich - 287776

Packaging
5 g in glass bottle

Sigma Aldrich - 66892

Other Notes
Chiral modifier for asymmetric LAH reductions of ketones1,2; Use of silyl ketene acetals of its esters in asymmetric Mukaiyama reactions3; Base used for the resolution of acids4
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