(-)-Bis[(S)-1-phenylethyl]amine
- Product Name
- (-)-Bis[(S)-1-phenylethyl]amine
- CAS No.
- 56210-72-1
- Chemical Name
- (-)-Bis[(S)-1-phenylethyl]amine
- Synonyms
- Tamsulosin Impurity 29;bis[(1S)-1-phenylethyl]amine;(S,S)-Bis-(1-phenylethyl)amin;(S)-bis((S)-1-phenylethyl)amine;(-)-Bis[(S)-1-phenylethyl]amine;(?)-Bis[(S)-1-phenylethyl]amine;(-)-bis[(s)-α-methylbenzyl]amine;(S)-(-)-Bis-(1-phenylethyl)-amine;(-)-Bis[(S)-1-phenylethyl]amine 99%;(S-(R* R*))-(-)-BIS(ALPHA-METHYLBENZYL)&
- CBNumber
- CB1499311
- Molecular Formula
- C16H19N
- Formula Weight
- 225.33
- MOL File
- 56210-72-1.mol
(-)-Bis[(S)-1-phenylethyl]amine Property
- Melting point:
- ~260 °C
- Boiling point:
- 86 °C0.05 mm Hg(lit.)
- alpha
- -197 º (NEAT)
- Density
- 0.987 g/mL at 25 °C(lit.)
- refractive index
- n20/D 1.5525(lit.)
- Flash point:
- >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 activity
- [α]/D 159°, c = 2 in ethanol
- Water Solubility
- Immiscible with water.
- CAS DataBase Reference
- 56210-72-1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 433810
- Product name
- (?)-Bis[(S)-1-phenylethyl]amine
- Purity
- 99%
- Packaging
- 1g
- Price
- $63.8
- Updated
- 2024/03/01
- Product number
- 433810
- Product name
- (?)-Bis[(S)-1-phenylethyl]amine
- Purity
- 99%
- Packaging
- 10g
- Price
- $350
- Updated
- 2024/03/01
- Product number
- H27106
- Product name
- (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
- Packaging
- 1g
- Price
- $46.65
- Updated
- 2024/03/01
- Product number
- H27106
- Product name
- (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
- Packaging
- 5g
- Price
- $158
- Updated
- 2024/03/01
- Product number
- H27106
- Product name
- (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
- Packaging
- 25g
- Price
- $590
- Updated
- 2024/03/01
(-)-Bis[(S)-1-phenylethyl]amine Chemical Properties,Usage,Production
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).
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
Raw materials
Preparation Products
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