30275-30-0

Usage

Uses

Used in Chemical Synthesis:
(S)-1-PHENYL-2-(P-TOLYL)ETHYLAMINE is used as an intermediate for the preparation of γ-nitroaldehydes with quaternary stereogenic centers. These γ-nitroaldehydes are essential in the synthesis of complex organic molecules and have potential applications in various industries.
Used in Pharmaceutical Industry:
(S)-1-PHENYL-2-(P-TOLYL)ETHYLAMINE is used as a reagent in the synthesis of optically active pyrethroids, which are compounds with insecticidal properties. These pyrethroids are effective against a range of insects, including mosquitoes, flies, and cockroaches, making them valuable in the development of insecticides for agricultural and public health applications.
Used in Research and Development:
(S)-1-PHENYL-2-(P-TOLYL)ETHYLAMINE is also utilized in the synthesis of 2,2''-Dihydroxybenzil, which acts as a stereodynamic probe for primary amines. This probe is controlled by steric strain and is essential in understanding the behavior and properties of primary amines, contributing to the advancement of chemical research and development.

InChI:InChI=1/C15H17N/c1-12-7-9-13(10-8-12)11-15(16)14-5-3-2-4-6-14/h2-10,15H,11,16H2,1H3

Upstream product

• 4714-21-0 4-methylstilbene 
• 71-43-2 benzene 
• 390-28-3 methoxamine 
• 111630-13-8 phenyl p-tolylmethyl ketone O-methyloxime 
• 106-42-3 para-xylene 
• 100-52-7 benzaldehyde 
• 492-41-1 (1R,2S)-norephedrine 
• 2430-99-1 1-phenyl-2-p-tolylethanone 
• 35675-44-6 4-methylphenylacetyl chloride 

Downstream Products

• 73758-00-6 (1R,4aS,10aR)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,5,6,7,8,9,10,10a-dodecahydro-phenanthrene-1-carboxylic acid (1-phenyl-2-p-tolyl-ethyl)-amide 
• 149365-93-5 (2,2-Diethoxy-ethyl)-(1-phenyl-2-p-tolyl-ethyl)-amine 
• 30339-30-1 (S)-2-(4-methylphenyl)-1-phenylethylamine 
• 30339-32-3 (R)-1-phenyl-2-(p-tolyl)ethylamine 
• 78934-98-2 N-[(1'-phenyl-2'-p-tolyl)-ethyl]-propiolamide 
• 57151-31-2 1-(2-methoxy-phenyl)-4-(1-phenyl-2-p-tolyl-ethyl)-piperazine 

Relevant academic research and scientific papers

General and selective synthesis of primary amines using Ni-based homogeneous catalysts

The development of base metal catalysts for industrially relevant amination and hydrogenation reactions by applying abundant and atom economical reagents continues to be important for the cost-effective and sustainable synthesis of amines which represent highly essential chemicals. In particular, the synthesis of primary amines is of central importance because these compounds serve as key precursors and central intermediates to produce value-added fine and bulk chemicals as well as pharmaceuticals, agrochemicals and materials. Here we report a Ni-triphos complex as the first Ni-based homogeneous catalyst for both reductive amination of carbonyl compounds with ammonia and hydrogenation of nitroarenes to prepare all kinds of primary amines. Remarkably, this Ni-complex enabled the synthesis of functionalized and structurally diverse benzylic, heterocyclic and aliphatic linear and branched primary amines as well as aromatic primary amines starting from inexpensive and easily accessible carbonyl compounds (aldehydes and ketones) and nitroarenes using ammonia and molecular hydrogen. This Ni-catalyzed reductive amination methodology has been applied for the amination of more complex pharmaceuticals and steroid derivatives. Detailed DFT computations have been performed for the Ni-triphos based reductive amination reaction, and they revealed that the overall reaction has an inner-sphere mechanism with H2metathesis as the rate-determining step.

Alkaline-metal-catalyzed one-pot aminobenzylation of aldehydes with toluenes

A novel and easily accessible MN(SiMe3)2 (M = Li or Na)/Cs2CO3 co-catalyzed benzylation of in situ generated N-(trimethylsilyl) aldimines with toluene derivatives has been successfully developed. The catalyst exhibits high chemoselectivity for deprotonation of toluenes at the benzylic position. The utility of this system is exemplified by the one-pot synthesis of a diverse array of bioactive 1,2-diarylethylamines with excellent efficiency and broad functional group tolerance.

Method for producing optically active chrysanthemic acid

Disclosed is a method for producing an optically active chrysanthemic acid, which method is characterized by optical resolution of a chrysanthemic acid having a trans isomer ratio of not less than 70% and an optical purity of 2% e.e. to less than 10% e.e. with an optically active organic.

Process for producing optically active 3,3,3-Trifluoro-2-Hydroxy-2-Methylpropionic acid, and salt thereof

There are disclosed are a diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):

10,5-(Iminomethano)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene and derivatives. Potent PCP receptor ligands

IDDC (3, 10,5-(iminomethano)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene) and a series of substituted derivatives were synthesized and evaluated in vitro for their ability to displace tritiated MK-801 ([3H]-2) from its specific binding site in guinea pig brain homogenate. Substitution at the 3- position of 3 with bromine, chlorine, and fluorine led to increased binding affinity. In contrast, substitution of donor groups at the 3-position gave decreased binding affinities, as did all substitutions at the 7-position and on nitrogen. Where racemic mixtures were resolved, the (+)-optical antipodes were more active than their enantiomers or racemates. The most active ligand found in this study was (+)-13e (IC50 = 15.5 ± 4.5 nM). The affinity of (+)-13e for the PCP receptor makes it among the most potent ligands known. In vitro neuroprotection was demonstrated by 3, (+)-3, and (+)-6 (N-Me-IDDC) against glutamate-induced cell death in rat hippocampal cells.

Process for producing optically active amines

Disclosed is a process for producing an optically active amine represented by the formula (IV) STR1 wherein R7 and R8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) STR2 wherein R1 denotes an alkyl group, aryl group or aralkyl group; R2 denotes a hydrogen atom, alkyl group or aralkyl group; R3 denotes an aryl group or a substituent represented by the formula (II) STR3 wherein R4 and R5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers STR4 wherein R6 denotes an alkyl group, aralkyl group or alkyl-substituted silyl group, and R7 and R8 are as defined above. The optically active amine obtained can be used as a resolving agent for preparing medicinal agents, agricultural chemicals, or intermediates thereof.

Method for producing optically active amines

A method for producing an optically active amine which is an important compound as a resolving agent for medicines, agricultural chemicals, intermediates thereof, etc is disclosed.

Regiochemistry on Photoamination of Stilbene Derivatives with Ammonia via Electron Transfer

The regiochemistry of photoamination of 1,2-diarylethene (1) with ammonia in the presence of p-dicyanobenzene (DCNB) has been investigated.The photoamination of stilbene and p,p'-dimethoxystilbene gave 1-amino-1,2-diphenylethane and 1-amino-1,2-bis(p-methoxyphenyl)ethane, respectively.The photoamination of unsymmetric 1-aryl-2-phenylethene having an alkoxy group on the para position occurred selectively to give 1-amino-2-aryl-1-phenylethane.On the other hand, the photoamination of 1-aryl-2-phenylethene having a methyl and chloro group on the para position or methoxy group on the meta and ortho positions gave both 1-amino-2-aryl-1-phenylethane and 1-amino-1-aryl-2-phenylethane.The regiochemistry is related with the distribution of positive charge in the cation radicals of 1 generated from photochemical electron transfer to DCNB.

Synthesis of amine derivatives

An amine of the formula, STR1 wherein R1, R2, R3, R4 and R5 are each hydrogen, alkyl or the like and n is 1, 2 or 3, including α-phenyl-β-(p-tolyl)-ethylamine, which is useful as an optically resolving agent, an intermediate of medicines and the like, is effectively produced by a novel process comprising hydrolysis of the corresponding nitrile of the formula, STR2 wherein R1, R2, R3, R4, R5 and n are the same as above, followed by alkali-decomposition of the resulting amide of the formula, STR3 wherein R1, R2, R3, R4, R5 and n are the same as above. An amide including the above one is effectively produced by hydrolysis of the corresponding nitrile in the presence of a base and hydrogen peroxide using an organic quaternary ammonium salt and/or a tertiary amine as a catalyst.

Arterial wall cholesterol ester reducing cyclopropanyl-bearing amides

Cyclopropanyl-group-bearing-amides, eg N-[1-(benzyl)-2-(phenyl)ethyl]-cis-2-octyl-cyclopropanoctanamide and N-(α-methyl-benzyl)-(cis)-2-octyl-cyclopropanoctanamide, are useful as pharmaceutical agents and are obtainable, eg by reacting a mixed anhydride of a cyclopropanyl-group bearing-long chain carboxylic acid with an appropriate amino compound.