56210-72-1

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 NO: 56210-72-1
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.33
• Mol File: 56210-72-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: ~260 °C
• Boiling Point: 86 °C0.05 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.987 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00143mmHg at 25°C
• Refractive Index: n20/D 1.5525(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 8.79±0.29(Predicted)
• Water Solubility: Immiscible with water.
• CAS DataBase Reference: (-)-Bis[(S)-1-phenylethyl]amine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Bis[(S)-1-phenylethyl]amine(56210-72-1)
• EPA Substance Registry System: (-)-Bis[(S)-1-phenylethyl]amine(56210-72-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 3
• Hazardous Substances Data: 56210-72-1(Hazardous Substances Data)

Usage

Uses

(-)-Bis[(S)-1-phenylethyl]amine is used as a chiral resolution reagent in organic synthesis.

InChI:InChI=1/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

Upstream product

• 98-85-1 1-Phenylethanol 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 98-86-2 acetophenone 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 10024-74-5 (R,R)-N,N-bis-(1-phenylethyl)amine 
• 100-47-0 benzonitrile 
• 13280-20-1 1-phenylethanimine 
• 130562-15-1 [1-(2-Fluoro-phenyl)-eth-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 445-27-2 2'-Fluoroacetophenone 
• 100-41-4 ethylbenzene 
• 618-36-0 rac-methylbenzylamine 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 284662-16-4 (S,S)-N-bromoacetyl-bis(α-methylbenzyl)amine 
• 364782-99-0 N,N-bis[(1R)-1-phenylethyl]prop-2-enamide 
• 376355-58-7 N,N-bis-[(S)-1-phenylethyl]dibenzo[d,f][1,3,2]dioxaphosphepin-6-amine 
• 500103-26-4 O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-bis[(S,S)-1-phenyl-ethyl]phosphoramidite 
• 201732-49-2 ((P)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 201732-49-2 ((M)-bis-3,3'-dimethyl-naphthaleno[1,2-f;2,1-d]-1,3-dioxa-2-phosphacycloheptan-2-yl)-(R,R)-bis(1-phenylethyl)amine 
• 246236-74-8 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid bis-((S)-1-phenyl-ethyl)-amide 
• 246236-72-6 (2R,3S)-3-Phenyl-oxirane-2-carboxylic acid bis-((S)-1-phenyl-ethyl)-amide 
• 712352-08-4 (S)-(+)-(3,5-dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-[(1R)-1-phenethyl]amine 
• 1033190-47-4 C₁₈H₂₀BrNO 
• 1020396-85-3 (S,S)-N-(2,10-dimethyl-12H-5,7-dioxa-6-phosphadibenzo[a,d]cycloocten-6-yl)bis(1-phenylethyl)amine 
• 10024-74-5 (R*,R*)-N-(1'-phenylethyl)-1-phenylethylamine 

Relevant articles and documents

An Iridium Catalytic System Compatible with Inorganic and Organic Nitrogen Sources for Dual Asymmetric Reductive Amination Reactions

Asymmetric reductive amination (ARA) is one of the most promising methods for the synthesis of chiral amines. Herein we report our efforts on merging two ARA reactions into a single-step transformation. Catalyzed by a complex formed from iridium and a steric hindered phosphoramidite, readily available and inexpensive aromatic ketones initially undergo the first ARA with ammonium acetate to afford primary amines, which serve as the amine sources for the second ARA, and finally provide the enantiopure C2-symmetric secondary amine products. The developed process competently enables the successive coupling of inorganic and organic nitrogen sources with ketones in the same reaction system. The Br?nsted acid additive plays multiple roles in this procedure: it accelerates the formation of imine intermediates, minimizes the inhibitory effect of N-containing species on the iridium catalyst, and reduces the primary amine side products.

One-Pot Synthesis of Symmetrical Tertiary and Secondary Amines from Carbonyl Compounds, Ammonium Carbonate and Carbon Monoxide as a Reductant

Rh-catalyzed one-step synthesis of tertiary and secondary amines from aldehydes and ketones, ammonium carbonate serving as nitrogen source, and carbon monoxide as a reducing agent has been developed. Aliphatic and aromatic aldehydes lead to the corresponding tertiary symmetrical amines in 69–83 % yields. Aromatic and aliphatic ketones lead to the corresponding secondary symmetrical amines which were obtained in 62–79 % yields.

B(C6F5)3-Catalyzed Asymmetric Reductive Amination of Ketones with Ammonia Borane

The first example of metal-free B(C6F5)3-catalyzed asymmetric reduction amination of ketones with chiral α-methylbenzylamine (α-MBA) using ammonia borane as the reductant is reported. This one-pot method has a broad substrate scope and provides various chiral amines in 81-95% yield with 80-99% de. This protocol was further applied in the total synthesis of cinacalcet.