bis[(1S)-1-phenylethyl]amine hydrochloride

• ChemBase ID: 131148
• Molecular Formular: C16H20ClN
• Molecular Mass: 261.7897
• Monoisotopic Mass: 261.12842733
• SMILES: C[C@@H](c1ccccc1)N[C@@H](C)c1ccccc1.Cl
• Canonical SMILES: C[C@@H](c1ccccc1)N[C@H](c1ccccc1)C.Cl
• InChI: InChI=1S/C16H19N.ClH/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16;/h3-14,17H,1-2H3;1H/t13-,14-;/m0./s1
• InChIKey: ZBQCLJZOKDRAOW-IODNYQNNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis[(1S)-1-phenylethyl]amine hydrochloride
• IUPAC Traditional name: bis[(1S)-1-phenylethyl]amine hydrochloride
• Synonyms: (-)-Bis[(S)-1-phenylethyl]amine hydrochloride; [S-(R*,R*)]-(-)-Bis(-α-methylbenzyl)amine hydrochloride; (-)-Bis[(S)-α-methylbenzyl]amine hydrochloride; [S-(R*,R*)]-(-)-双(-α-甲苄基)胺 盐酸盐; (-)-双[(S)-α-甲苄基]胺 盐酸盐; (-)-双[(S)-1-苯基乙基]胺 盐酸盐

Database IDs

• CAS Number: 40648-92-8
• MDL Number: MFCD00216671
• Beilstein Number: 4723969
• PubChem SID: 24868213; 24849134; 162225426
• PubChem CID: 12353077

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.9554847
• LogD (pH = 7.4): 2.212895
• Log P: 4.0892177
• Molar Refractivity: 72.7562 cm^3
• Polarizability: 28.934862 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~260 °C; 261-263 °C(lit.)
• Optical Rotation: [α]20/D -73.0°, c = 3 in ethanol; [α]20/D -73±2°, c = 3% in ethanol

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

Product Information

• Purity: ≥98.0% (AT); 97%
• Linear Formula: [C6H5CH(CH3)]2NH·HCl
• Empirical Formula (Hill Notation): C16H19N · HCl

DETAILS

Sigma Aldrich - 445940

Application
The addition of lithium enolates to chiral 2-(aminomethyl)acrylates prepared from this C2-symmetrical amine results in the diastereoselective formation of β-amino acid esters.1 This amine has been employed as a chiral base in the synthesis of 3-substituted- and 3,3-disubstituted-γ-butyrolactones via enantioselective deprotonation of cyclobutane derivatives.2 It has also been used in a new method for the synthesis of β-aminophosphine derivatives of potential value as asymmetric ligands.3

Sigma Aldrich - 15145

Other Notes
The corresponding chiral lithium amide is used as base for the enantioselective deprotonation of ketones.1,2,3,4
Packaging
5, 25 g in glass bottle