3261-62-9

Usage

Uses

Used in Chemical Synthesis:
4-Methylphenethylamine is used as a chemical intermediate for the preparation of secondary amides. It plays a crucial role in the amidation of sophorolipid ethyl ester, which is an important step in the synthesis of various chemical compounds.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-Methylphenethylamine, due to its amine functional group, could potentially be used in the pharmaceutical industry for the synthesis of various drugs and medications. Amines are known to be versatile building blocks in the development of pharmaceutical compounds.
Used in Research and Development:
4-Methylphenethylamine may also find applications in research and development, particularly in the field of organic chemistry and material science. Its unique chemical properties could be exploited to create new compounds or materials with specific characteristics and applications.

InChI:InChI=1/C9H13N/c1-8-2-4-9(5-3-8)6-7-10/h2-5H,6-7,10H2,1H3/p+1

Upstream product

• 2947-61-7 (4-methylphenyl)acetonitrile 
• 6529-51-7 2-(4-methylphenyl)ethyl bromide 
• 2742-70-3 Bis-((E)-2-p-tolyl-vinyl)-diazene N,N'-dioxide 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 72538-33-1 2-p-tolylnitroethane 
• 74533-76-9 3-(4-methylphenyl)propanamide 
• 861018-73-7 2-(4-methylphenethyl)isoindoline-1,3-dione 
• 64-17-5 ethanol 
• 622-75-3 1,4-phenylenediacetonitrile 
• 101671-00-5 (Z)-1-methyl-4-(2-nitrovinyl)benzene 
• 104-87-0 4-methyl-benzaldehyde 
• 699-02-5 4-Methylphenethyl alcohol 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 622-97-9 1-ethenyl-4-methylbenzene 

Downstream Products

• 699-02-5 4-Methylphenethyl alcohol 
• 76833-31-3 2-(4-methyl-cyclohexyl)-ethylamine 
• 108878-45-1 N-(4-methyl-phenethyl)-β-alanine nitrile 
• 26011-73-4 N-[2-(p-tolyl)ethyl] acetamide 
• 86427-24-9 3-(N-p-tolylethyliminomethyl)indole 
• 89516-38-1 2-acetyl-10-(p-tolylethylaminoacetyl)phenothiazine 
• 80554-84-3 2-(1H-Indol-3-yl)-2-oxo-N-(2-p-tolyl-ethyl)-acetamide 
• 80554-79-6 2-(2-Methyl-1H-indol-3-yl)-2-oxo-N-(2-p-tolyl-ethyl)-acetamide 
• 129397-53-1 N-Amoc-DL-α-methyl tryptophanyl-2-(4-methylphenyl)ethylamide 
• 80654-59-7 (4,4-Diphenyl-butyl)-(2-p-tolyl-ethyl)-amine 
• 112697-20-8 [6-Methylsulfanyl-1-(tetrahydro-furan-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-(2-p-tolyl-ethyl)-amine 
• 86886-26-2 (E)-3-(2,4-Dihydroxy-6-methyl-pyrimidin-5-yl)-N-(2-p-tolyl-ethyl)-acrylamide 
• 80884-15-7 3-(4-Methoxy-phenyl)-2-[(2-p-tolyl-ethylamino)-methyl]-3H-quinazolin-4-one 
• 95833-39-9 6-Iodo-3-(4-methoxy-phenyl)-2-[(2-p-tolyl-ethylamino)-methyl]-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Reduction of Aliphatic and Aromatic Nitro Compounds with Sodium Borohydride in Tetrahydrofuran Using 10percent Palladium-on-Carbon as Catalyst

Aliphatic and aromatic nitro compounds are reduced to amino compounds in good yields with sodium borohydride in tetrahydrofuran using 10percent palladium-on-carbon as catalyst.

Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination

Direct and selective synthesis of primary amines from easily available precursors is attractive yet challenging. Herein, we report the rapid synthesis of primary amines from alkenes via metal-free regioselective hydroamination at room temperature. Ammonium carbonate was used as ammonia surrogate for the first time, allowing for efficient conversion of terminal and internal alkenes into linear, α-branched, and α-tertiary primary amines under mild conditions. This method provides a straightforward and powerful approach to a wide spectrum of advanced, highly functionalized primary amines which are of particular interest in pharmaceutical chemistry and other areas.

Benzimidazole fragment containing Mn-complex catalyzed hydrosilylation of ketones and nitriles

The synthesis of a new bidentate (NN)–Mn(I) complex is reported and its catalytic activity towards the reduction of ketones and nitriles is studied. On comparing the reactivity of various other Mn(I) complexes supported by benzimidazole ligand, it was observed that the Mn(I) complexes bearing 6-methylpyridine and benzimidazole fragments exhibited the highest catalytic activity towards monohydrosilylation of ketones and dihydrosilylation of nitriles. Using this protocol, a wide range of ketones were selectively reduced to the corresponding silyl ethers. In case of unsaturated ketones, the chemoselective reduction of carbonyl group over olefinic bonds was observed. Additionally, selective dihydrosilylation of several nitriles were also achieved using this complex. Mechanistic investigations with radical scavengers suggested the involvement of radical species during the catalytic reaction. Stoichiometric reaction of the Mn(I) complex with phenylsilane revealed the formation of a new Mn(I) complex.

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Ruthenium(II)-cored supramolecular organic framework-mediated recyclable visible light photoreduction of azides to amines and cascade formation of lactams

Ru(bpy)3]2+-cored supramolecular organic framework SMOF-1, assembled from a [Ru(bpy)3]2+-derived hexaarmed molecule and cucurbit[8]uril, has been demonstrated to heterogeneously catalyze visible light-induced reduction of phenyl, benzyl, 2-phenylethyl and 3-phenylpropyl azides in acetonitrile to produce the corresponding amines in good to high yields. For the last two kinds of azides that bear a CO2Me group at the para-position of the benzene ring, cascade reactions take place to generate the corresponding lactams in high yields. Compared with homogeneous control [Ru(bpy)3]Cl2, SMOF-1 exhibits remarkably increased photocatalysis activity as a result of synergistic effect of the [Ru(bpy)3]2+ units that form cubic cages to host the azide molecules and related intermediates. Moreover, SMOF-1 displays high recyclability and considerable photocatalysis activity after 3 to 12 runs.

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

Synthesis and antioxidant characteristic of novel thiazolidinone derivatives

A series of novel thiazolidinone derivatives have been synthesized by solventless condensation of N-alkylamines with arylaldehydes at room temperature followed by a microwave assisted solventless addition of thioglycollic acid to the resultant imines. The synthesized compounds are characterized by 1H NMR, 13C NMR, MS and X-ray techniques and one of the synthesized thiazolidinones has been evaluated for its antioxidant property.

Enhanced reduction of C-N multiple bonds using sodium borohydride and an amorphous nickel catalyst

Amorphous nickel powder (Ni0) was utilised as a catalyst under mild, aqueous, basic conditions for enhancing the sodium borohydride-mediated reduction of C-N multiple bonds such as oximes, imines, hydrazones and nitriles to produce the corresponding amines in good to excellent yields.

Reduction of nitriles to amines with H2 catalyzed by nonclassical ruthenium hydrides - Water-promoted selectivity for primary amines and mechanistic investigations

Catalytic hydrogenation of nitriles to amines by nonclassical ruthenium hydride complexes derived from PNP pincer ligands is described. Aromatic as well as aliphatic nitriles are reduced to the corresponding primary amines. Hydrogen pressure influences the selectivity for the primary amines. The mechanism of nitrile reduction with nonclassical ruthenium hydride pincer complexes is investigated by DFT calculations. A catalytic cycle involving the coordination of nitrile trans to the pincer backbone after an initial hydride rearrangement at the ruthenium center, and the subsequent first transfer of the hydride ligand to the carbon center of the nitrile ligand is suggested as a possible reaction mechanism. Interestingly, the use of water as additive increases the selectivity for the primary amines and the rate of the reactions. Selective synthesis of primary amines by the catalytic hydrogenation of nitriles with nonclassical ruthenium hydride pincer complexes is reported. Use of water as additive increases the selectivity and rate of the reactions. Possible catalytic cycles were identified for this important reaction of industrial significance by means of DFT calculations. Copyright