70138-19-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-METHYLPHENYL)ETHANAMINE is used as a precursor in the synthesis of other pharmaceuticals and research chemicals. Its ability to stimulate the sympathetic nervous system and act as a dopamine reuptake inhibitor makes it a valuable component in the development of medications targeting various conditions.
Used in Medical Applications:
1-(3-METHYLPHENYL)ETHANAMINE is used in medical applications for its potential psychoactive effects and its influence on neurotransmitter levels in the brain. Its ability to affect the levels of dopamine can be beneficial in the treatment of certain neurological and psychiatric disorders.
However, due to its potential for abuse and addiction, 1-(3-METHYLPHENYL)ETHANAMINE is considered a controlled substance, and its use in medical applications is strictly regulated.

Upstream product

• 585-74-0 3-Methylacetophenone 
• 540-69-2 ammonium formate 
• 77287-34-4 formamide 
• 23040-54-2 1-m-tolyl-ethanone oxime 

Downstream Products

• 42071-04-5 1-(m-Methylphenyl)-1-formylaminethan 
• 138457-19-9 (1R)-1-(3-methylphenyl)ethan-1-amine 
• 138457-18-8 (-)-(S)-1-(3-methylphenyl)ethylamine 
• 42071-13-6 N-Methyl-N-<1-(m-methylphenyl)-ethyl>-amin 
• 1105678-36-1 3-{[1-(3-methylphenyl)ethyl]amino}-4-(pyridin-4-ylamino)cyclobut-3-ene-1,2-dione 
• 816431-99-9 C₉H₁₃N*C₁₂H₁₅NO₃ 
• 1227845-02-4 C₉H₁₃N*C₁₂H₁₅NO₃ 
• 1350639-70-1 6-(4-methoxyphenyl)-N-(1-m-tolylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 1350639-87-0 4-(4-((1-(m-tolyl)ethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenol hydrobromide 
• 1605305-81-4 (R)-2-methoxy-N-(1-m-tolylethyl)acetamide 
• 585-74-0 3-Methylacetophenone 
• 1295522-07-4 1,7-dimethyl-3,4-diphenyl-isoquinoline 
• 1439557-96-6 C₃₇H₄₀N₆O₃S 
• 1070875-05-6 N-(1-(m-methylphenyl)ethyl)acetamide 

Relevant academic research and scientific papers

Ultra-small cobalt nanoparticles from molecularly-defined Co-salen complexes for catalytic synthesis of amines

We report the synthesis of in situ generated cobalt nanoparticles from molecularly defined complexes as efficient and selective catalysts for reductive amination reactions. In the presence of ammonia and hydrogen, cobalt-salen complexes such as cobalt(ii)-N,N′-bis(salicylidene)-1,2-phenylenediamine produce ultra-small (2-4 nm) cobalt-nanoparticles embedded in a carbon-nitrogen framework. The resulting materials constitute stable, reusable and magnetically separable catalysts, which enable the synthesis of linear and branched benzylic, heterocyclic and aliphatic primary amines from carbonyl compounds and ammonia. The isolated nanoparticles also represent excellent catalysts for the synthesis of primary, secondary as well as tertiary amines including biologically relevant N-methyl amines.

Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant

The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.

The Synthesis of Primary Amines through Reductive Amination Employing an Iron Catalyst

The reductive amination of ketones and aldehydes by ammonia is a highly attractive method for the synthesis of primary amines. The use of catalysts, especially reusable catalysts, based on earth-abundant metals is similarly appealing. Here, the iron-catalyzed synthesis of primary amines through reductive amination was realized. A broad scope and a very good tolerance of functional groups were observed. Ketones, including purely aliphatic ones, aryl–alkyl, dialkyl, and heterocyclic, as well as aldehydes could be converted smoothly into their corresponding primary amines. In addition, the amination of pharmaceuticals, bioactive compounds, and natural products was demonstrated. Many functional groups, such as hydroxy, methoxy, dioxol, sulfonyl, and boronate ester substituents, were tolerated. The catalyst is easy to handle, selective, and reusable and ammonia dissolved in water could be employed as the nitrogen source. The key is the use of a specific Fe complex for the catalyst synthesis and an N-doped SiC material as catalyst support.

Rh(III)-Catalyzed Coupling of N-Chloroimines with α-Diazo-α-phosphonoacetates for the Synthesis of 2 H-Isoindoles

We report herein the first use of N-chloroimines as effective synthons for directed C-H functionalization. Rh(III)-catalyzed coupling of N-chloroimines with α-diazo-α-phosphonoacetates allows for efficient dechlorinative/dephosphonative access to 2H-isoindoles. Further deesterification under Ni(II) catalysis enables the complete elimination of reactivity-assisting groups and full exposure of reactivity of C3 and N2 ring atoms for attaching structurally distinct appendages.

Substituent effects on chiral resolutions of derivatized 1-phenylalkylamines by heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin GC stationary phase

Chiral resolutions of trifluoroacetyl-derivatized 1-phenylalkylamines with different type and position of substituent were investigated by capillary gas chromatography by using heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-cyclodextrin diluted in OV-1701 as a chiral stationary phase. The influence of column temperature on retention and enantioselectivity was examined. All enantiomers of meta-substituted analytes as well as fluoro-substituted analytes could be resolved. Temperature had a favorable influence on enantioselectivity for small amines with substituents at the ortho-position. The type of substituent at the stereogenic center of amines also had a crucial effect as the ethyl group led to poor enantioseparation. Among all analytes studied, trifluoroacetyl-derivatized 1-(2′-fluorophenyl)ethylamine exhibited baseline resolution with the shortest analysis time.

METHOD FOR THE HOMOGENEOUS CATALYTIC REDUCTIVE AMINATION OF CARBONYL COMPOUNDS

The present invention relates to a method for the reductive amination of a carbonyl compound, comprising one or more carbonyl groups amenable to reductive amination, forming the corresponding primary amine, characterized in that the reaction is carried out in the presence of a homogeneously dissolved catalyst complex K, comprising at least one metal atom from Group 8, 9 or 10 of the periodic table, bearing a bidentate phosphane ligand, a carbonyl ligand, a neutral ligand and a hydride ligand, and also an acid as co-catalyst.

Direct Synthesis of Primary Amines via Ruthenium-Catalysed Amination of Ketones with Ammonia and Hydrogen

A highly selective reductive amination of ketones to primary amines with ammonia and hydrogen using a simple ruthenium catalyst has been developed. The protocol described constitutes an efficient and direct atom-economical approach en route to α-methylbenzylamine derivatives in good to high yields. The presence of catalytic amounts of aluminum triflate turned out to be crucial for achieving high conversion towards primary amines.

Synthesis and in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines

A series of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines have been synthesised, characterised and tested for their in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity. The compounds were prepared from ethyl cyanoacetate and α-bromoacetophenones via the 2-amino-3-ethoxycarbonyl-5- aryl-pyrroles and 4-chloro-6-arylpyrrolopyrimidines. Aromatic substitution with benzylic amines was performed by conventional thermal substitution, and palladium catalysed coupling. The two methods resulted in similar yields, but the palladium coupling had the benefit of lower chemical consumption and reduced reaction times. Eight of the new compounds had IC50 values in the range of 2.8-9.0 nM. Four of these have a fluorine atom positioned at sites otherwise potentially susceptible to oxidative metabolism. Structural variation of the 6-aryl group indicated that the inhibitory action was only moderately sensitive to modifications in this fragment. However, the potency depended strongly on the structure of the aromatic part of the 4-amino group, and any aromatic substitution except fluorine reduced the in vitro activity. The cellular EGFR internalization response of selected compounds was evaluated using HeLa cells. Three fluorinated derivatives had a pronounced effect in inhibiting EGFR internalization.

Identification and SAR of squarate inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

A novel series of inhibitors for mitogen activated protein kinase-activated protein kinase 2 (MK-2) are reported. These squarate based inhibitors were identified via a high-throughput screen. An MK2 co-structure with the starting ligand was obtained and a structure based approach was followed to optimize potency and selectivity.

Synthesis and chiral recognition ability of O-phenyl ethylphosphonothioic acid with a conformationally flexible phenoxy group for CH/π interaction

Enantiopure O-phenyl ethylphosphonothioic acid 1 was easily obtained by the enantioseparation of racemic 1, which was prepared from commercially available phosphorothioic trichloride in four steps. Enantiopure 1 was found to show an excellent chiral recognition ability for various 1-arylethylamine derivatives during the diastereomeric salt formation. In particular, enantiopure 1 was able to recognize the chirality of o- and m-substituted 1-arylethylamine derivatives, of which the chirality is generally difficult to establish by conventional resolving agents. X-ray crystallographic analyses of the less-soluble diastereomeric salts revealed that the conformation of the phenoxy group in enantiopure 1 could change in the diastereomeric salt crystals and that the excellent chiral recognition ability of enantiopure 1 resulted from the effective CH/π interaction of the phenoxy phenyl group.