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| | (-)-Bis[(S)-1-phenylethyl]amine Basic information |
| Product Name: | (-)-Bis[(S)-1-phenylethyl]amine | | Synonyms: | (S-(R* R*))-(-)-BIS(ALPHA-METHYLBENZYL)&;(-)-Bis[(S)-1-phenylethyl]amine, 99% (99+% EE/GLC);(S,S)-Bis-(1-phenylethyl)amin;(-)-bis[(s)-α-methylbenzyl]amine;(S)-(-)-Bis-(1-phenylethyl)-amine hydrochloride;(-)-Bis[(S)-1-phenylethyl]amine, ChiPros 99%, ee 98+%;(-)-Bis[(S)-α-methylbenzyl]amine, [S-(R*,R*)]-(-)-Bis(α-methylbenzyl)amine;(-)-Bis[(S)-1-phenylethyl]amine | | CAS: | 56210-72-1 | | MF: | C16H19N | | MW: | 225.33 | | EINECS: | | | Product Categories: | | | Mol File: | 56210-72-1.mol | ![(-)-Bis[(S)-1-phenylethyl]amine Structure](CAS/GIF/56210-72-1.gif) |
| | (-)-Bis[(S)-1-phenylethyl]amine Chemical Properties |
| 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. | | pka | 8.79±0.29(Predicted) | | form | liquid | | 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 Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37 | | WGK Germany | 3 | | F | 3 | | HS Code | 2921199990 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (-)-Bis[(S)-1-phenylethyl]amine Usage And Synthesis |
| 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. |
| | (-)-Bis[(S)-1-phenylethyl]amine Preparation Products And Raw materials |
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