80272-38-4

Basic information

• Product Name: 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one
• Synonyms: 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one;2,3-Dihydro-6-trifluoromethyl-3-(4-fluorophenyl)-1H-inden-1-one;3-(4-Fluorophenyl)-2,3-dihydro-6-trifluoromethyl-1H-inden-1-one;Einecs 279-438-1;3-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)-2,3-DIHYDROINDEN-1-ONE(WXG01216);3-(4-FLUOROPHENYL)-6-(TRIFLUOROMETHYL)-2,3-DIHYDROINDEN-1-ONE
• CAS NO: 80272-38-4
• Molecular Formula: C₁₆H₁₀F₄O
• Molecular Weight: 294.2436128
• EINECS: 279-438-1
• Mol File: 80272-38-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 346.6°Cat760mmHg
• Flash Point: 132.8°C
• Appearance: /
• Density: 1.356g/cm³
• Vapor Pressure: 5.69E-05mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one(80272-38-4)
• EPA Substance Registry System: 3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-one(80272-38-4)

Safety Data

• Hazardous Substances Data: 80272-38-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H10F4O/c17-11-4-1-9(2-5-11)13-8-15(21)14-7-10(16(18,19)20)3-6-12(13)14/h1-7,13H,8H2

Upstream product

• 116616-85-4 3-Amino-1-cyano-1-(4-fluoro-phenyl)-5-trifluoromethyl-1H-indene-2-carboxylic acid methyl ester 
• 328-87-0 2-chloro-5-(trifluoromethyl)benzonitrile 
• 459-22-3 4-fluorophenylacetonitrile 
• 85663-11-2 ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-3-(4-fluorophenyl)propanoate 
• 85118-34-9 ethyl 3-<2-bromo-4-(trifluoromethyl)phenyl>-2-cyano-2-propenoate 
• 85118-24-7 2-bromo-4-(trifluoromethyl)benzaldehyde 
• 80272-16-8 3-<2-bromo-4-(trifluoromethyl)phenyl>-3-(4-fluorophenyl)propanoic acid 

Downstream Products

• 85663-29-2 1-[(1R,3S)-6-Fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-4-((E)-3-phenyl-allyl)-piperazine 
• 85663-30-5 1-[(1R,3R)-6-Fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-4-((E)-3-phenyl-allyl)-piperazine 
• 80274-12-0 trans-1-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>-4-(2-phenylethyl)piperazine 
• 80274-13-1 cis-1-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>-4-(2-phenylethyl)piperazine 
• 85663-48-5 cis-4-<3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl>-1-piperazineethanol 
• 85663-38-3 2-{4-[(1R,3S)-6-Fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-piperazin-1-yl}-acetamide 
• 85663-35-0 1-{4-[(1R,3S)-6-Fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-piperazin-1-yl}-2-methyl-propan-2-ol 
• 85663-27-0 trans-1-(cyclopropylmethyl)-4-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>piperazine 
• 85663-28-1 cis-1-(cyclopropylmethyl)-4-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>piperazine 
• 85663-34-9 trans-1-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>-4-(2-hydroxy-1-propyl)piperazine 
• 85663-34-9 cis-1-<6-fluoro-3-(4-fluorophenyl)indan-1-yl>-4-(2-hydroxy-1-propyl)piperazine 
• 85663-25-8 1-Ethyl-4-[(1R,3S)-6-fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-piperazine 
• 85663-26-9 1-Ethyl-4-[(1S,3S)-6-fluoro-3-(4-fluoro-phenyl)-indan-1-yl]-piperazine 
• 80274-28-8 1-cyclopropylcarbonyl-4-(3-(4'-fluorophenyl)-6-fluoro-1-indanyl)piperazine 

Relevant articles and documents

Application of (2-Cyanoaryl)arylacetonitriles in Cyclization and Annulation Reactions. Preparation of 3-Arylindans, 4-Aryl-3,4-dihydronaphthalenes, 4-Arylisoquinolines, 1-Aminonaphthalenes, and Heterocyclic Analogues

(2-Cyanoaryl)arylacetonitriles, obtained from o-halogen-substituted cyanoaromatics and arylacetonitriles may be alkylated with methyl chloroacetate.Subsequent abstraction of the proton adjacent to the ester group followed by attack of the anion at the aromatic cyano group gives rise to annulated 1-aminocyclopentenes by a Dieckmann-type reaction.The homologous esters similarly produce annulated 1-aminocyclohexenes.The generality of this annulation method is demonstrated by preparation of derivatives of 1-amino-1H-indene, 4-amino-6H-cyclopentathiophene, 5-amino-7H-pyrindine, 1-amino-3,4-dihydronaphthalene, and 5-amino-2,9-dihydro-1H-cyclopentisoquinoline.Hydrolysis and decarboxylation of these compounds leads to ketones as exemplified by synthesis of 3-arylindan-1-ones and 4-aryl-3,4-dihydro-1(2H)-naphthalen-1-ones.When treated with hydrogen bromide, the (2-cyanophenyl)phenylacetonitriles cyclize to -condensed 3-bromo-5-aryl-6-aminopyridines.Thus, derivatives of isoquinoline, thienopyridine, and 1,6-naphthyridine were prepared.

Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans

A series of 1-piperazino-3-phenylindans was synthesized and tested for neuroleptic and thymoleptic activity. Neuroleptic activity was found only in trans racemates and was associated with one of the enantiomers only. The potent and long-acting neuroleptic compound trans-4-[3-(4-fluorophenyl)-6-(trifluoromethyl)indan-1-yl]-1-piperazineeth anol (Lu 18-012, tefludazine) was developed by systematic variation of structural components. Thymoleptic activity was optimized, especially with respect to dopamine-uptake inhibition. No geometrical stereoselectivity was found with regard to dopamine-uptake inhibition, but a high enantioselectivity could be demonstrated for both cis and trans racemates. The most potent compounds were 1-piperazino-3-(3,4-dichlorophenyl)indans with IC50 values of about 2 nM for inhibition of dopamine uptake.