10181-67-6

Basic information

• Product Name: (R)-α-Ethyl-α-methylbenzylamine
• Synonyms: (1R)-1-Methyl-1-phenyl-1-propanamine;(1R)-1-Phenyl-1-methyl-1-propanamine;(R)-α-Ethyl-α-methylbenzylamine;[R,(+)]-α-Ethyl-α-methylbenzylamine
• CAS NO: 10181-67-6
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.2328
• Mol File: 10181-67-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-α-Ethyl-α-methylbenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-Ethyl-α-methylbenzylamine(10181-67-6)
• EPA Substance Registry System: (R)-α-Ethyl-α-methylbenzylamine(10181-67-6)

Safety Data

• Hazardous Substances Data: 10181-67-6(Hazardous Substances Data)

Usage

Description

(R)-α-Ethyl-α-methylbenzylamine, with the molecular formula C12H17N, is an organic amine characterized by a chiral center. This unique feature allows it to exist in two enantiomeric forms, (R) and (S). As a versatile compound, it plays a significant role in various industrial applications, particularly in the pharmaceutical sector.

Uses

Used in Pharmaceutical Industry:
(R)-α-Ethyl-α-methylbenzylamine is used as an intermediate for the synthesis of various drugs, including antihistamines and antihypertensive agents. Its presence in these medications aids in the treatment of allergies and high blood pressure, respectively.
Used as a Chiral Resolving Agent:
In the field of asymmetric synthesis, (R)-α-Ethyl-α-methylbenzylamine serves as a chiral resolving agent. This application is crucial for obtaining specific enantiomers of a compound, which can have different biological activities and properties.
Used as a Catalyst in Organic Synthesis:
(R)-α-Ethyl-α-methylbenzylamine also functions as a catalyst in organic synthesis, facilitating and enhancing the efficiency of various chemical reactions. This role is essential for the production of complex organic compounds and contributes to the development of new pharmaceuticals and other bioactive substances.
Used in Asymmetric Synthesis and Medicinal Chemistry:
(R)-α-Ethyl-α-methylbenzylamine's potential applications in asymmetric synthesis and medicinal chemistry make it a valuable asset in the development of novel pharmaceuticals and bioactive compounds. Its unique properties and reactivity contribute to the advancement of these fields, ultimately leading to the creation of innovative treatments and therapies.

Upstream product

• 100-47-0 benzonitrile 
• 6948-04-5 1-methyl-1-phenyl-n-propylamine 
• 195438-46-1 Methyl-ethylketon-N'-2-phenyl-2-butylhydrazon 
• 131154-15-9 4-Methyl-benzenesulfinic acid ((R)-1-methyl-1-phenyl-but-3-enyl)-amide 
• 131154-18-2 (R)-(1-methyl-1-phenyl-but-3-enyl)amine 
• 131154-21-7 ((R)-2-[1,3]Dithian-2-yl-1-methyl-1-phenyl-ethyl)-carbamic acid methyl ester 
• 131154-20-6 ((R)-1-Methyl-3-oxo-1-phenyl-propyl)-carbamic acid methyl ester 
• 131154-19-3 ((R)-1-Methyl-1-phenyl-but-3-enyl)-carbamic acid methyl ester 
• 737777-15-0 (S)-N-[(1S,2R,S_s)-1-methyl-1-phenyl-2-(p-tolylsulfinyl)propyl]-p-toluenesulfinamide 
• 65440-68-8 [S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide 
• 737777-38-7 (1S,2R,S_s)-1-methyl-1-phenyl-2-(p-tolylsulfinyl)propylamine 
• 193904-72-2 ((R)-1-Methyl-1-phenyl-propyl)-carbamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 131154-22-8 ((R)-1-Methyl-1-phenyl-propyl)-carbamic acid methyl ester 
• 64551-09-3 (+)-2-Phenyl-2-butylhydrazin 

Relevant articles and documents

Synthesis of highly enantioenriched C-TERTIARY amines from boronic esters: Application to the synthesis of igmesine

Better than all the rest: Tertiary boronic esters, readily available using the lithiation-borylation reaction, have been converted into tertiary alkylamines in very high ee. The work has been applied to a short, modular, and fully stereocontrolled synthesis of the pharmaceutical igmesine and chiral 2,2-disubstituted piperidines.

Stereoselective addition of α-sulfinyl carbanions to N-p-tolylsulfinylketimines: Synthesis of optically pure 1,2,2′-trialkyl-2- aminoethanols

The reactions of lithium carbanions derived from both enantiomers of methyl (1) and ethyl p-tolyl sulfoxide (2) with (S)-N-arylsulfinylketimines 3 and 4 took place in a highly stereoselective manner and good isolated yields. The configuration of the carbon bonded to nitrogen relies exclusively on the N-sulfinylimine configuration. When ethyl p-tolyl sulfoxide (2) is use as nucleophile, two chiral centers are created simultaneously, where the configuration of the carbon bonded to the sulfur is mainly controlled by 2. The asymmetric induction increases with the temperature, being total at room temperature in the case of the matched pair of reactants. A non-oxidative Pummerer reaction on the obtained aminosulfoxides allows a straightforward synthesis of optically pure 1,2-ethanolamines with one or two chiral centers, including amino alcohols with a bulky quaternary carbon bonded to the amine group.

Stereoselective Addition Reactions of Chiral N-Benzylidene-p-toluenesulfinamides. Asymmetric Syntheses of β- and γ-Amino Acids

Chiral N-benzylidene-p-toluenesulfinamides 2 were prepared by the reaction of benzonitril with alkyllithium in ether followed by (-)-l-menthyl (S)-p-tolylsulfinate.Treatment of 2 with allylmagnesium bromide in ether at 0 deg C gave the adducts (R)-7 with excellent stereoselectivity.Pure chiral sulfinamides 7 were converted into β- and γ-amino acids in four and five steps, respectively.