diphenyl(2R)-pyrrolidin-2-ylmethanol

• ChemBase ID: 66956
• Molecular Formular: C17H19NO
• Molecular Mass: 253.33886
• Monoisotopic Mass: 253.14666423
• SMILES: N1[C@H](CCC1)C(O)(c1ccccc1)c1ccccc1
• Canonical SMILES: OC(c1ccccc1)(c1ccccc1)[C@H]1CCCN1
• InChI: InChI=1S/C17H19NO/c19-17(16-12-7-13-18-16,14-8-3-1-4-9-14)15-10-5-2-6-11-15/h1-6,8-11,16,18-19H,7,12-13H2/t16-/m1/s1
• InChIKey: OGCGXUGBDJGFFY-MRXNPFEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl(2R)-pyrrolidin-2-ylmethanol
• IUPAC Traditional name: diphenyl(2R)-pyrrolidin-2-ylmethanol
• Synonyms: (R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol; (R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol; (R)-(+)-alpha,alpha-Diphenylprolinol; (R)-α,α-Diphenyl-2-pyrrolidinemethanol; α,α-Diphenyl-D-prolinol; (R)-(+)-Alpha,alpha-Diphenyl-2-pyrrolidinemethanol; α,α-Diphenyl-D-prolinol; (R)-2-(Diphenylhydroxymethyl)pyrrolidine; (R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol; (R)-α,α-二苯基-2-吡咯烷甲醇; α,α-二苯基-D-脯氨醇; (R)-2-(二苯基羟甲基)吡咯烷; (R)-(+)-α,α-二苯基脯氨醇

Database IDs

• CAS Number: 22348-32-9
• MDL Number: MFCD00077754
• Beilstein Number: 4353363
• PubChem SID: 24863890; 162032692
• PubChem CID: 7045371

CALCULATED PROPERTIES

• Acid pKa: 12.901563
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.35732114
• LogD (pH = 7.4): 0.039381664
• Log P: 2.8763463
• Molar Refractivity: 77.1829 cm^3
• Polarizability: 30.58561 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 76-78°C; 77-80 °C; 77-80 °C(lit.)
• Optical Rotation: [α]20/D +69±3°, c = 3% in chloroform; [α]20/D +69°, c = 3 in chloroform; +57.5 (c=3 in methanol)

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 98%; 99%
• Grade: purum
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C17H19NO

DETAILS

Sigma Aldrich - 382337

Packaging
1, 5 g in glass bottle
100 mg in glass bottle
Application
Used to prepare the corresponding oxazaborolidines for the borane-mediated asymmetric reduction of ketones.1

REFERENCES

• Chiral precursor for the asymmetric reduction of ketones, see following entry.