191084-78-3

Basic information

• Product Name: (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine
• Synonyms: (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine
• CAS NO: 191084-78-3
• Molecular Weight: 281.277
• Mol File: 191084-78-3.mol

Chemical Properties

• CAS DataBase Reference: (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine(CAS DataBase Reference)
• NIST Chemistry Reference: (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine(191084-78-3)
• EPA Substance Registry System: (4-methoxyphenyl)[2-(2-phenyl-1,1,1-trifluoroethyl)] amine(191084-78-3)

Safety Data

• Hazardous Substances Data: 191084-78-3(Hazardous Substances Data)

Upstream product

• 456-56-4 phenyl trifluoromethylsulfide 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 2101-87-3 p-methoxy-phenylazide 
• 869653-41-8 C₁₅H₁₂F₃NO 
• 104-94-9 4-methoxy-aniline 
• 100-52-7 benzaldehyde 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 202869-51-0 4-methoxy-N-(2,2,2-trifluoro-1-phenylethylidene)benzenamine 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 3262-89-3 triphenylboroxine 
• 1005385-31-8 N-(2,2,2-trifluoro-1-methoxyethyl)-4-methoxyaniline 
• 14796-89-5 4-methoxy-N-(triphenylphosphoran-ylidene)-aniline 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 

Downstream Products

• 293743-66-5 N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-2-phenethyl)-2-methoxybenzamide 
• 293743-63-2 N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-2-phenethyl)-4-methoxybenzamide 
• 293743-64-3 N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-2-phenethyl)-benzamide 
• 293743-65-4 N-(4-methoxyphenyl)-N-(1,1,1-trifluoro-2-phenethyl)-3-methoxybenzamide 

Relevant articles and documents

Novel and effective synthesis of trifluoromethylated amines by use of an Et3GeNa/C6H5SCF3 combination

Efficient synthesis of trifluoromethylated amine derivatives by use of an Et3GeNa/C6H5SCF3 combination is described. This reaction proceeded smoothly to give the desired compound in excellent yield.

Method for preparing trifluoroethylamine derivative through reductive amination reaction of trifluoromethyl ketone

The invention discloses a method for preparing a trifluoroethylamine derivative through a reductive amination reaction of trifluoromethyl ketone. According to the method, trifluoromethyl ketone and p-methoxyaniline serve as the raw materials, an organic hydrogen donor serves as a reducing agent, and the trifluoroethylamine derivative is obtained through a heating reaction in an organic solvent in the presence of an acid catalyst. The method is mild in reaction condition, simple in technology and convenient and rapid to operate; the obtained trifluoroethylamine derivative has good potential biological activity and can be used as an organic synthetic intermediate.

Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57-91% yield and with greater than 92% ee in most cases.

Palladium(II)-catalyzed enantioselective synthesis of α- (trifluoromethyl)arylmethylamines

Trifluoromethylacetaldimines, generated in situ from the corresponding N,O-acetals, undergo 1,2-addition of arylboroxines under palladium(II) catalysis to generate a variety of α-(trifluoromethyl)arylmethylamines with good to high enantioselectivity (up to 97% ee). The pyridine-oxazolidine (PyOX) class of ligands was found to be particularly suitable for this transformation, which proceeds without exclusion of ambient air and moisture.

Enantioselective Pd-catalyzed hydrogenation of fluorinated imines: Facile access to chiral fluorinated amines

An enantioselective hydrogenation of simple fluorinated imines has been developed using Pd(OCOCF3)2/(R)-Cl-MeO-BIPHEP as a catalyst, and up to 94% ee was achieved. This method provides an efficient route to enantioenriched fluorinated amines.

Preparation of tri- and difluoromethylated amines from aldimines using (trifluoromethyl)trimethylsilane

Addition of a trifluoromethyl group into aldimines was accomplished using (trifluoromethyl)trimethylsilane with tetraalkylammonium fluorides as initiators, and the resulting adducts were converted to difluoromethylated imines in the presence of excess flu

α-(trifluoromethyl)amine derivatives via nucleophilic trifluoromethylation of nitrones

(Trifluoromethyl)trimethylsilane (TMSCF3) reacts with nitrones to afford α-(trifluoromethyl)hydroxylamines protected as O-trimethylsilyl ethers. Potassium t-butoxide initiates the nucleophilic trifluoromethylation. The reaction works best with α,N-diaryl nitrones, and the conditions are compatible with a range of substituents on the aryl groups. Acidic deprotection of the nitrone/TMSCF3 adducts generates α-(trifluoromethyl)hydroxylamines. Catalytic hydrogenation of the adducts produces α-(trifluoromethyl)amines. Nitrone/TMSCF3 adducts with strong electron-withdrawing groups on the α-aryl ring or heterocyclic α-aryl groups undergo an elimination/addition sequence to generate α, α-bis(trifluoromethyl)amines. Nitrones with alkyl groups bound directly to the 1,3-dipolar moiety fail to react with TMSCF3, but trifluoromethylation of β,γ-unsaturated nitrones followed by reduction of the double bond can circumvent this limitation.

Acyclic amides as estrogen receptor ligands: Synthesis, binding, activity and receptor interaction

We have prepared a series of bisphenolic amides that mimic bibenzyl and homobibenzyl motifs commonly found as substructures in ligands for the estrogen receptor (ER). Representative members were prepared from three classes: N-phenyl benzamides, N-phenyl acetamides, and N-benzyl benzamides; in some cases the corresponding thiocarboxamides and sulfonamides were also prepared. Of these three classes, the N-phenyl benzamides had the highest affinity for ER, the N-phenyl acetamides had lower, and the N-benzyl benzamides were prone to fragmentation via a quinone methide intermediate. In the N-phenyl benzamide series, the highest affinity analogues had bulky N-substituents; a CF3 group, in particular, conferred high affinity. The thiocarboxamides bound better than the corresponding carboxamides and these bound better than the corresponding sulfonamides. Binding affinity comparisons suggest that the p-hydroxy group on the benzoate ring, which contributes most to the binding, is playing the role of the phenolic hydroxyl of estradiol. Computational studies and NMR and X-ray crystallographic analysis indicate that the two anilide systems studied have a strong preference for the s-cis or exo amide conformation, which places the two aromatic rings in a syn orientation. We used this structural template, together with the X-ray structure of the ER ligand binding domain, to elaborate an additional hydrogen bonding site on a benzamide system that elevated receptor binding further. When assayed on the individual ER subtypes, ERα and ERβ, these compounds show modest binding affinity preference for ERα. In a reporter gene transfection assay of transcriptional activity, the amides generally have full to nearly full agonist character on ERα, but have moderate to full antagonist character on ERβ. One high affinity carboxamide is 500-fold more potent as an agonist on ERα than on ERβ. This work illustrates that ER ligands having simple amide core structures can be readily prepared, but that high affinity binding requires an appropriate distribution of bulk, polarity, and functionality. The strong conformational preference of the core anilide function in all of these ligands defines a rather rigid geometry for further structural and functional expansion of these series. Copyright (C) 2000 Elsevier Science Ltd.