benzyl[(1R)-1-phenylethyl]amine

• ChemBase ID: 69409
• Molecular Formular: C15H17N
• Molecular Mass: 211.30218
• Monoisotopic Mass: 211.13609955
• SMILES: N([C@H](C)c1ccccc1)Cc1ccccc1
• Canonical SMILES: C[C@H](c1ccccc1)NCc1ccccc1
• InChI: InChI=1S/C15H17N/c1-13(15-10-6-3-7-11-15)16-12-14-8-4-2-5-9-14/h2-11,13,16H,12H2,1H3/t13-/m1/s1
• InChIKey: ZYZHMSJNPCYUTB-CYBMUJFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl[(1R)-1-phenylethyl]amine
• IUPAC Traditional name: benzyl[(1R)-1-phenylethyl]amine
• Synonyms: (R)-N-Benzyl-1-phenylethanamine; D-(+)-N-Benzyl-alpha-methylbenzylamine; (R)-(+)-N-Benzyl-1-phenylethylamine; R-(+)-N-Benzyl-1-phenylethylamine; (R)-(+)-N-(1-Phenylethyl)benzylamine; (R)-(+)-N-Benzyl-1-phenylethylamine; (R)-(+)-N-Benzyl-α-methylbenzylamine; (R)-(+)-N-苄基-1-苯乙胺; (R)-(+)-N-(1-苯乙基)苄胺; (R)-(+)-N-苄基-1-苯乙胺; (R)-(+)-N-苄基-α-甲基苄胺

Database IDs

• CAS Number: 38235-77-7
• MDL Number: MFCD00015010
• Beilstein Number: 3589990
• PubChem SID: 24848339; 162035135; 24867044
• PubChem CID: 1268086

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.55898386
• LogD (pH = 7.4): 1.8762265
• Log P: 3.6726427
• Molar Refractivity: 68.3374 cm^3
• Polarizability: 27.088657 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 171 °C/15 mmHg(lit.); 171°C/15mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.01 g/mL at 25 °C(lit.); 1.010
• Refractive Index: 1.5630; n20/D 1.564(lit.)
• Optical Rotation: [α]20/D +38°, neat; [α]20/D +58±2°, c = 5% in ethanol; +39 (neat)

Safety Information

• Storage Warning: Air Sensitive; IRRITANT
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P501A; P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥97.5%; ≥98.5% (sum of enantiomers, GC); 95+%; 98%; ChiPros 99+%, ee 96+%
• Grade: produced by BASF; puriss.
• Optical Purity: ee: ≥97% (HPLC); enantiomeric excess: ≥97.5%
• Linear Formula: C6H5CH(CH3)NHCH2C6H5

DETAILS

Sigma Aldrich - 431737

Application
Chiral amine used for enantioselective deprotonations.1,2,3,4
Packaging
10 mL in glass bottle
50 mL in poly bottle

Sigma Aldrich - 726915

Packaging
25, 100 g in glass bottle
Legal Information
ChiPros is a registered trademark of BASF SE

Sigma Aldrich - 13765

Other Notes
The metal amide of this base is used for diastereoselective Michael additions yielding β-amino acids1; Base for enantioselective ketone enolate formation2,3

REFERENCES

• N-Metallated derivatives are useful chiral bases. The Mg derivative effects the enantioselective deprotonation of 2,6-disubstituted cyclohexanones: Chem. Commun., 479 (2000); Synlett, 1253 (2001); 1017 (2003):