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ChemicalBook--->CAS DataBase List--->56210-72-1

56210-72-1

56210-72-1 Structure

56210-72-1 Structure
IdentificationBack 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 PropertiesBack 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 activity]

[α]/D 159°, c = 2 in ethanol
[Water Solubility ]

Immiscible with water.
[CAS DataBase Reference]

56210-72-1
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37
[WGK Germany ]

3
[F ]

3
[HS Code ]

2921199990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Tetrahydrofuran-->Toluene-->Sodium borohydride-->p-Toluenesulfonic acid-->Acetophenone-->L-1-Phenylethylamine-->HEAVY DISTILLATE
Hazard InformationBack 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
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

(-)-Bis[(S)-1-phenylethyl]amine(56210-72-1)IR
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