10024-74-5

Basic information

• Product Name: ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE
• Synonyms: Bis(α-methylbenzyl)amine;N-(α-Methylbenzyl)-α-methylbenzenemethanamine;BenzeneMethanaMine, a-Methyl-N-(1-phenylethyl)-
• CAS NO: 10024-74-5
• Molecular Formula: C₁₆H₁₉N
• Molecular Weight: 225.3365
• Mol File: 10024-74-5.mol

Chemical Properties

• Boiling Point: 356.85°C (rough estimate)
• Flash Point: 137.2°C
• Appearance: /
• Density: 1.0180
• Refractive Index: 1.5730
• CAS DataBase Reference: ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE(10024-74-5)
• EPA Substance Registry System: ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE(10024-74-5)

Safety Data

• Hazardous Substances Data: 10024-74-5(Hazardous Substances Data)

Usage

Uses

Used in the Polyurethane Industry:
ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE is used as a catalyst for the production of polyurethane foam, facilitating the formation of urethane linkages in the polymerization process. This results in the creation of high-quality and durable polyurethane materials, which are widely used in various applications such as insulation, cushioning, and flexible foams.
Used in Pharmaceutical and Agrochemical Industries:
ALPHA,ALPHA'-DIMETHYLDIBENZYLAMINE is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its role in these industries is crucial for the development of new and effective products in the medical and agricultural sectors.

Upstream product

• 40636-57-5 (αS)-α-methyl-N-(1-phenylethylidene)benzenemethanamine 
• 2408-37-9 2,2,6-trimethylcyclohexan-1-one 
• 25102-87-8 N-(α-methyl)benzylidene 1-phenylethanamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 89103-78-6 (-)-(R)-N-(1-phenylethyl)-α-methylbenzylideneamine 
• 127104-51-2 (R*,R*)-diethyl N,N-bis(1-phenylethyl)amino phosphate 
• 68199-31-5 (R)-N-(α-methylbenzylidene)-α-methylbenzylamine 
• 100483-17-8 (E)-N-<1-phenylethylidene>-1-phenylethylamine 
• 98-86-2 acetophenone 
• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 104873-95-2 [(R)-1-(4-Chloro-phenyl)-ethyl]-((R)-1-phenyl-ethyl)-amine 
• 618-36-0 rac-methylbenzylamine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 100-52-7 benzaldehyde 

Downstream Products

• 134431-02-0 methyl (3R,αR,α'R)-3-(N,N-bis(α-methylbenzyl)amino)butanoate 
• 134431-04-2 tert-butyl (3R,αR,α'R)-3-(N,N-bis(α-methylbenzyl)amino)butanoate 
• 134431-03-1 benzyl (3R,αR,α'R)-3-(N,N-bis(α-methylbenzyl)amino)butanoate 
• 137219-70-6 2-{[Bis-((S)-1-phenyl-ethyl)-amino]-methyl}-acrylic acid tert-butyl ester 
• 90933-78-1 C₁₆H₁₈NO 
• 197387-11-4 lithium (S,S)-bis(α-methylbenzyl)amide 
• 232267-74-2 (S)-3-[Bis-((S)-1-phenyl-ethyl)-amino]-hept-6-enoic acid ethyl ester 
• 246236-70-4 (S,S)-(E)-N-cinnamoyl-bis(α-methylbenzyl)amine 
• 712352-08-4 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 
• 712352-08-4 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 
• 284662-16-4 (S,S)-N-bromoacetyl-bis(α-methylbenzyl)amine 

Relevant articles and documents

Mixtures of chiral phosphorous acid diesters and achiral P ligands in the enantio- and diastereoselective hydrogenation of ketimines

Try this cocktail! Ligand systems comprising a monodentate phosphorous acid diester derived from binol (La) and an achiral monodentate P ligand (Lb), such as a phosphite, are surprisingly efficient in the stereoselective Ir-catalyzed hydrogenation of ketimines (see scheme).

Metal-free transfer hydrogenation catalysis by B(C6F 5)3

The activation of amines by B(C6F5)3 is shown to effect the catalytic racemization of a chiral amine. Extending this strategy to a bimolecular process, catalytic transfer hydrogenation of imines, enamines, and N-heterocycles is demonstrated using iPr2NH as the source of hydrogen and a catalytic amount of the Lewis acid B(C 6F5)3.

Diastereoselective hydrogenation and kinetic resolution of imines using rhodium/diphosphine catalyzed hydrogenation

Kinetic resolution of racemic α-methylbenzyl amine can be achieved with 98% e.e. of the remaining amine at 70% conversion using the Rhodium/2S,4S-BDPP catalyzed asymmetric hydrogenation of imines. The same catalyst will hydrogenate optically pure α-methylbenzyl amines with a diastereoselectivity of up to 333:1.

A new atom-economical and selective synthesis of secondary and tertiary alkylamines by means of Cp*Iridium complex catalyzed multiple N-alkylation of ammonium salts with alcohols without solvent

A new atom-economical and selective synthetic method for secondary and tertiary alkylamines has been achieved by means of (pentamethylcyclopentadienyl) iridium (Cp*Ir) complex catalyzed multiple N-alkylations of ammonium salts with primary and secondary alcohols without solvent. Georg Thieme Verlag Stuttgart.

Diastereoselective Addition of Methylcopper- and Dimethylcuprate-Boron Trifluoride Reagents to (S)-(N-Alkylidene)-1-phenylethylamines

The reactions of methylcopper- and dimethylcuprate-boron trifluoride reagents with aldimines derived from (S)-1-phenylethylamine afford with good diastereoselectivity (S,S)-amines from aromatic imines, but the (R,S)-amine from an aliphatic imine

ENANTIOSELECTIVE REDUCTION OF ACETOPHENONE BY BORANE.CHIRAL AMINE COMPLEXES

The enantioselective reduction of acetophenone by the borane.chiral amine complexes BH3.1a - BH3.1d affords 1-phenyl-1-ethanol with o.y. up to 42percent.

Method for synthesizing chiral phosphite ligand based on R - 2 - phenylethylamine

The invention discloses a method for synthesizing chiral phosphite ligand based on R - 2 -phenylethylamine. To the method, R - 2 -phenylethylamine is reacted with acetophenone to obtain the imine intermediate, and then is mixed with H. 2 Under

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.

Preparation method of chiral amine compounds

The invention discloses a preparation method of chiral amine compounds. The preparation method of the chiral amine compounds specifically comprises the following steps: adding ketone compounds and chiral auxiliary (S)-a-phenylethylamine or (R)-a-phenylethylamine to an organic solvent to prepare an imine intermediate under the action of a large-steric-hindrance boron catalyst and a water removing agent; adding a reducing agent to the imine intermediate without separation and purification, and preparing the chiral amine compounds with a one-pot method. By calculation, the product yield is 81%-96%, and the highest de value can reach 99%. Compared with the prior art, the use amount of the large-steric-hindrance boron catalyst in the method can be reduced to 0.1 mol%, use of the equivalent metal catalyst is avoided from the source, and the method has the characteristics of being simple to operate, mild in reaction condition, wide in substrate applicability, environmental friendly and the like, and has better application value and potential economic and social benefits.