| Identification | Back Directory | [Name]
(-)-Bis[(S)-1-phenylethyl]amine | [CAS]
56210-72-1 | [Synonyms]
(S,S)-Bis-(1-phenylethyl)amin
(-)-Bis[(S)-1-phenylethyl]amine
(S)-bis((S)-1-phenylethyl)amine
(-)-bis[(s)-α-methylbenzyl]amine
(-)-Bis[(S)-1-phenylethyl]amine 99%
(S-(R* R*))-(-)-BIS(ALPHA-METHYLBENZYL)&
(S)-(-)-Bis-(1-phenylethyl)-amine hydrochloride
(-)-Bis[(S)-1-phenylethyl]amine, 99% (99+% EE/GLC)
(-)-Bis[(S)-1-phenylethyl]amine, ChiPros 99%, ee 98+%
(-)-Bis[(S)-1-phenylethyl]aMine, ChiPros|r, 99%, ee 98+%
(-)-Bis[(S)-α-methylbenzyl]amine, [S-(R*,R*)]-(-)-Bis(α-methylbenzyl)amine | [Molecular Formula]
C16H19N | [MDL Number]
MFCD00243087 | [MOL File]
56210-72-1.mol | [Molecular Weight]
225.33 |
| Chemical Properties | Back Directory | [Melting point ]
~260 °C
| [alpha ]
-197 º (NEAT) | [Boiling point ]
86 °C0.05 mm Hg(lit.)
| [density ]
0.987 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5525(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
readily sol common organic solvents (ether, THF, chloroform, etc.); insol H2O. | [form ]
liquid | [pka]
8.79±0.29(Predicted) | [color ]
Clear, colourless | [Optical Rotation]
[α]/D 159°, c = 2 in ethanol | [Water Solubility ]
Immiscible with water. | [InChI]
InChI=1S/C16H19N/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16/h3-14,17H,1-2H3/t13-,14-/m0/s1 | [InChIKey]
NXLACVVNHYIYJN-KBPBESRZSA-N | [SMILES]
N([C@H](C1=CC=CC=C1)C)[C@H](C1=CC=CC=C1)C | [CAS DataBase Reference]
56210-72-1 |
| Hazard Information | Back Directory | [Uses]
(-)-Bis[(S)-1-phenylethyl]amine is used as a chiral resolution reagent in organic synthesis. | [Preparation]
Preparative Methods of (-)-(S,S)-α,α′-Dimethyldibenzylamine: minor improvements to the original catalytic hydrogenation procedure have been
described (eq 1). This method provides (S,S)-(-)-(1) with an optical purity of only 70%. Enantiomerically
pure (S,S)-(-)-(1) can be obtained by recrystallization of the hydrochloride salt of this enriched material from
water or the benzoate salt from isopropanol. A chemical reduction procedure has also been described that
yields optically active (S,S)-(1) with 74% enantiomeric excess (eq 2). A significant improvement to the
former procedures is the diastereoselective hydrogenation of imines catalyzed by rhodium/chiral
diphosphines, which yields (S,S)-(1) with an optical purity of 99.4% (eq 3).
![(-)-Bis[(S)-1-phenylethyl]amine synthesis](/NewsImg/2025-01-10/6387210492052306913464980.png "(-)-Bis[(S)-1-phenylethyl]amine synthesis") | [General Description]
(-)-(S,S)-α,α′-Dimethyldibenzylamine is a starting material for the formation of chiral amide reagents; useful in the stereospecific deprotonation of
prochiral ketones, and as a chirality transfer agent in the reactions of prochiral enolates; stereoselective
conjugate addition of organometallic reagents to unsaturated carbonyl systems.[1] | [storage]
(-)-(S,S)-α,α′-Dimethyldibenzylamine is no special precautions have been noted in the literature. The free base is
a clear distillable liquid that should be stored under an inert atmosphere to prevent air oxidation. Long term
storage may lead to some coloration of the material. | [Purification Methods]
Purification of (-)-(S,S)-α,α′-Dimethyldibenzylamine: the free base can be distilled. The HCl salt can be recrystallized from water, which removes
diastereomeric impurities. The benzoate salt can be recrystallized from isopropanol.
| [References]
1. (a) Eleveld, M. B.; Hogeveen, H.; Schudde, E. P. JOC 1986, 51, 3635. (b) Yoshida, T.; Harada, K. BCJ 1972, 45,
3706. |
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