(-)-Bis[(S)-1-phenylethyl]amine

ChemicalBook > CAS DataBase List > (-)-Bis[(S)-1-phenylethyl]amine

(-)-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

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(-)-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

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36/37
WGK Germany: 3
F: 3
HS Code: 2921199990

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 433810
Product name: (?)-Bis[(S)-1-phenylethyl]amine
Purity: 99%
Packaging: 1g
Price: $63.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: 433810
Product name: (?)-Bis[(S)-1-phenylethyl]amine
Purity: 99%
Packaging: 10g
Price: $350
Updated: 2024/03/01

Alfa Aesar

Product number: H27106
Product name: (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
Packaging: 1g
Price: $46.65
Updated: 2024/03/01

Alfa Aesar

Product number: H27106
Product name: (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
Packaging: 5g
Price: $158
Updated: 2024/03/01

Alfa Aesar

Product number: H27106
Product name: (-)-Bis[(S)-1-phenylethyl]amine, ChiPros?, 99%, ee 98+%
Packaging: 25g
Price: $590
Updated: 2024/03/01

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(-)-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

p-Toluenesulfonic acid Toluene Sodium borohydride Acetophenone L-1-Phenylethylamine Tetrahydrofuran HEAVY DISTILLATE

Preparation Products

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