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Chemical Structure| 1997-80-4
Chemical Structure| 1997-80-4
Structure of 1997-80-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1997-80-4 ]

CAS No. :1997-80-4 MDL No. :MFCD03092900
Formula : C9H8BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :AZLYAPKPZBXCGX-UHFFFAOYSA-N
M.W : 253.06 Pubchem ID :594535
Synonyms :

Safety of [ 1997-80-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1997-80-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1997-80-4 ]

[ 1997-80-4 ] Synthesis Path-Downstream   1~42

  • 1
  • [ 1997-80-4 ]
  • [ 5052-95-9 ]
  • [ 5053-02-1 ]
  • 2
  • [ 1997-80-4 ]
  • 2<bis(4-fluorophenyl)methylthio>-ethylamine [ No CAS ]
  • [ 140890-68-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In various solvent(s) for 96h; Heating;
  • 4
  • [ 1997-80-4 ]
  • [ 603-35-0 ]
  • 2-(3-Trifluormethylphenyl)aethyltriphenylphosphonium-Ion [ No CAS ]
  • 5
  • [ 1997-80-4 ]
  • C8H8F(1+) [ No CAS ]
  • [ 25017-13-4 ]
  • C9H8F3(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Rk. m. BrCCl3;
YieldReaction ConditionsOperation in experiment
2-(3-Trifluormethyl-phenyl)-ethanol, HBr;
entspr. Phnylaceticacid, AlH4, PBr3;
  • 8
  • [ 1997-80-4 ]
  • N-methyl-N-<2-<bis(4-fluorophenyl)methylthio>ethyl>-2-(3-trifluoromethylphenyl)ethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3 / various solvent(s) / 96 h / Heating 2: 80 percent / HCOOH / H2O / 100 °C
  • 9
  • [ 1997-80-4 ]
  • [ 63035-56-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: PhLi
  • 10
  • [ 1997-80-4 ]
  • [ 63035-58-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: PhLi 3: (i) BF3-Et2O, LiAlH4, (ii) H2O2, aq. NaOH
  • 11
  • [ 1997-80-4 ]
  • [ 63035-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: PhLi 3: (i) AgOAc, I2, aq. AcOH, (ii) KOH, EtOH
  • 12
  • [ 351-35-9 ]
  • [ 1997-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: LiAlH4 3: PBr3
  • 14
  • [ 705-29-3 ]
  • [ 1997-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 2: aq. H2SO4 4: LiAlH4 5: PBr3
  • 15
  • [ 2338-76-3 ]
  • [ 1997-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. H2SO4 3: LiAlH4 4: PBr3
  • 16
  • [ 536-75-4 ]
  • [ 1997-80-4 ]
  • [ 129254-85-9 ]
YieldReaction ConditionsOperation in experiment
4 Preparation of 1-(3-trifluoromethylphenyl)-3-(4-pyridyl)-butane EXAMPLE 4 Preparation of 1-(3-trifluoromethylphenyl)-3-(4-pyridyl)-butane 1.0 g (9.35 mmol) of 4-ethylpyridine and 2.37 g (9.35 mmol) of 3-trifluoromethylphenethyl bromide were reacted in the same manner as in Example 1. The reaction product was purified to obtain 0.40 g of the desired compound (yield: 15.3%). The resulting compound was identified as 1-(3-trifluoromethylphenyl)-3-(4-pyridyl)-butane (hereinafter referred to as compound 4) by the following analytical results.
  • 17
  • [ 109859-85-0 ]
  • [ 1997-80-4 ]
  • [ 147520-36-3 ]
YieldReaction ConditionsOperation in experiment
32% 45 Prepared from 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 2-(3-trifluoromethyl-phenyl)-ethylbromide analogously to Example 1. EXAMPLE 45 3-[(N-(2-(3-Trifluoromethylphenyl)-ethyl)-piperidin-3-yl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one-hydrochloride Prepared from 3-[(piperidin-3-yl)-methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one and 2-(3-trifluoromethyl-phenyl)-ethylbromide analogously to Example 1. Yield: 32% of theory, Melting point: from 150° C. (decomp.). Rf value: 0.36 (silica gel, methylene chloride/methanol=10/1).
  • 19
  • [ 1997-80-4 ]
  • [ 17356-08-0 ]
  • C10H11F3N2S*BrH [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 2h; Reflux; Synthesis of mercaptan reagents 6 General procedure: Thiourea (7 mmol) was dissolved in 13.5 mL ethanol and the appropriate alkylbromide (7 mmol) was added. The mixture was stirred and heated under reflux for 2 h after which the reaction became homogenous. The reaction was allowed to cool to room temperature and the ethanol solvent was removed under reduced pressure. A solution of NaOH (10.5 mmol) in 8.75 mL water was added to the residue, and the reaction mixture was heated under reflux (120 C) for 2 h. The reaction was subsequently cooled to room temperature and aqueous H2SO4 (15%) was added. The mercaptan separated as oil droplets and was extracted to diethylether (30 mL). The organic phase was washed twice with water, dried over anhydrous Na2SO4 and removed under reduced pressure. This yielded the desired mercaptans which were used without further purification for the synthesis of 1, 3 and 4.
  • 20
  • [ 1997-80-4 ]
  • [ 1415676-47-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol / 2 h / Reflux 2.1: sodium hydroxide / water / 2 h / 120 °C 2.2: 20 °C 3.1: sodium hydroxide / ethanol; water / 1 h / Cooling with ice; Reflux
  • 21
  • [ 1997-80-4 ]
  • [ 1267977-24-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ethanol / 2 h / Reflux 2.1: sodium hydroxide / water / 2 h / 120 °C 2.2: 20 °C
  • 23
  • [ 1997-80-4 ]
  • [ 1316652-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide 2: copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; sodium L-ascorbate / water; dimethyl sulfoxide / 24 h / 20 °C / Combinatorial reaction / High throughput screening (HTS)
  • 24
  • [ 1997-80-4 ]
  • 4a-phenethyl-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
  • 4a-phenethyl-2-(3-(trifluoromethyl)phenethyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 20h; 5.1.5 General procedure E General procedure: A mixture of the amine 9, alkyl bromide (1.2 equiv) and NaHCO3 (2 equiv) in DMF (20 mL) was heated at 50 °C for 20 h. After cooling to room temperature, the reaction mixture was poured into ice-H2O, and the product was extracted with Et2O. The ethereal extracts were washed with saturated NH4Cl solution. After drying over Na2SO4, the solvent was removed in vacuo to afford an oil. The crude oil was subjected to flash chromatography on silica gel using 75% EtOAc in hexanes as the eluent to give the compounds 3a-h as a solid.
  • 25
  • [ 1997-80-4 ]
  • [ 1508310-77-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 120 h / 90 °C 2: tin(II) chloride dihdyrate; ethanol / 28 h / Reflux
  • 26
  • [ 1997-80-4 ]
  • [ 1508310-52-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium iodide; caesium carbonate / N,N-dimethyl-formamide / 120 h / 90 °C 2.1: tin(II) chloride dihdyrate; ethanol / 28 h / Reflux 3.1: HATU / dichloromethane / 0.17 h / 20 °C 3.2: 3 h / 20 °C
  • 28
  • [ 1997-80-4 ]
  • [ 108-00-9 ]
  • N,N-dimethyl-N'-[2-(3-trifluoromethylphenyl)ethyl]ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(3-trifluoromethylphenyl)-ethyl bromide With sodium iodide In ethanol for 1h; Reflux; Stage #2: N,N-dimethylethylenediamine In ethanol at 20℃; Reflux; N ,N-Dimethyl-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-ethane-1 ,2-diamine To a solution of 3-(trifluoromethyl)phenethyl bromide (1 .34 mL, 7.9 mmol) in 20 mL EtCH isadded Nal (3.58 g, 23.9 mmol). The suspension is refluxed for 1 h. The mixture is cooled toRT then a solution of 2-dimethylamino-ethylamine (4.32 mL, 39.5 mmol) in 15 mL EtCH is added dropwise. The mixture is stirred at RT for 2 h then refluxed overnight. The mixture is cooled to RT and EtCH is evaporated. 50 mL DCM is added and the white solid is filtered off. The mother liquid is washed with 50 mL water then the aqueous phase is extracted twicewith 25 mL DCM. The combined organic layer is dried over MgSC4, filtered and concentrated. Flash-chromatography on silica-gel (EtCAc I MeCH I TEA 80 : 18 : 2) yields 0.84 g (41%) of the title compound as a light orange oil. LC-B: tR = 0.50 mm; [M+H] = 261.22
  • 29
  • [ 1997-80-4 ]
  • 4a-(3-phenylpropyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
  • 4a-(3-phenylpropyl)-2-(3-(trifluoromethyl)phenethyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 20h; 3.1.3 Method C: general procedure for synthesis of compounds 10-12 General procedure: A mixture of the amine 9, alkyl bromide (1.2 equiv) and NaHCO3 (2 equiv) in DMF (20mL) was heated at 50°C for 20h. After cooling to room temperature, the reaction mixture was poured into ice- H2O, and the product was extracted with Et2O. The ethereal extracts were washed with saturated NH4Cl solution, dried over Na2SO4, and the solvent was removed in vacuo to afford an oil. The crude oil was subjected to flash chromatography on silica gel using 75% EtOAc in hexanes as the eluent to give the 10-12 as solids.
  • 30
  • [ 1997-80-4 ]
  • 4a-(4-phenylbutyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
  • 4a-(4-phenylbutyl)-2-(3-(trifluoromethyl)phenethyl)-1,2,3,4,4a,9a-hexahydrobenzofuro[2,3-c]pyridin-6-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; for 20h; 3.1.3 Method C: general procedure for synthesis of compounds 10-12 General procedure: A mixture of the amine 9, alkyl bromide (1.2 equiv) and NaHCO3 (2 equiv) in DMF (20mL) was heated at 50°C for 20h. After cooling to room temperature, the reaction mixture was poured into ice- H2O, and the product was extracted with Et2O. The ethereal extracts were washed with saturated NH4Cl solution, dried over Na2SO4, and the solvent was removed in vacuo to afford an oil. The crude oil was subjected to flash chromatography on silica gel using 75% EtOAc in hexanes as the eluent to give the 10-12 as solids.
  • 31
  • [ 1997-80-4 ]
  • tert-butyl (S,Z)-(((tert-butoxycarbonyl)amino)(2-(3-(6-hydroxynaphthalen-2-yl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methylene)carbamate [ No CAS ]
  • tert-butyl (S,Z)-(((tert-butoxycarbonyl)amino)(2-(3-(6-(3-(trifluoromethyl)phenethoxy)naphthalen-2-yl)-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl)methylene)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
8% With potassium carbonate; sodium iodide In ethanol at 100℃; for 0.25h; Microwave irradiation;
  • 32
  • [ 1997-80-4 ]
  • N-(3-hydroxybenzyl)-4-methoxy-N-(pyridin-4-ylmethyl)benzamide [ No CAS ]
  • 4-methoxy-N-(pyridin-4-ylmethyl)-N-(3-(3-(trifluoromethyl)phenethoxy)benzyl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With potassium carbonate In acetone at 56℃; for 18h; 5.1.3. Representative procedure for the synthesis of final compounds General procedure: Acetone (0.5 mL) was added to phenol (4-6) (50 mg,0.144 mmol). Then K2CO3 (39.7 mg, 0.287 mmol, 2eq.) and bromide(0.144 mmol,1eq.) were added and the reaction mixturewas stirredat 56 °C overnight. Thereafter, the reaction mixture was filtered,centrifuged, and the supernatant was evaporated to dryness. Thecrude was purified using prep TLC or Biotage flash column chromatographyto afford the desired final compound.
  • 33
  • [ 1997-80-4 ]
  • [ 52516-30-0 ]
  • 34
  • [ 1022094-52-5 ]
  • [ 1997-80-4 ]
  • C19H16F4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With manganese; 6,6'-dimethyl-2,2'-bipyridine; nickel(II) perchlorate hexahydrate; ytterbium(III) triflate In N,N-dimethyl acetamide at 25℃; for 12h; regioselective reaction;
  • 35
  • [ 1997-80-4 ]
  • [ 13858-85-0 ]
  • 2-(3-(trifluoromethyl)phenyl)-1-azaspiro[3.5]nonane [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.1333 g Stage #1: 2-(3-trifluoromethylphenyl)-ethyl bromide With magnesium In tetrahydrofuran Inert atmosphere; Schlenk technique; Stage #2: cyclohexanone O-methyloxime With titanium(IV) isopropylate In diethyl ether at 20℃; for 6h; Inert atmosphere;
  • 36
  • [ 433703-81-2 ]
  • [ 1997-80-4 ]
  • methyl 2-(4,8-dimethyl-2-oxo-7-(3-(trifluoromethyl)phenethoxy)-2H-chromen-3-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate In acetone Reflux;
  • 37
  • [ 137-43-9 ]
  • [ 1997-80-4 ]
  • C14H16BrF3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With nickel(II) iodide; C17H20N2O2; lithium bromide; zinc In 1-methyl-pyrrolidin-2-one at 30℃; for 24h; regioselective reaction;
  • 38
  • [ 1997-80-4 ]
  • 4-mercapto-indan-1-one [ No CAS ]
  • C18H15F3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-mercapto-indan-1-one With sodium hydride In tetrahydrofuran for 0.0833333h; Cooling with ice; Stage #2: 2-(3-trifluoromethylphenyl)-ethyl bromide In tetrahydrofuran at 20℃; for 4h; 1.2 General procedure for the preparation of intermediates c1-c29 General procedure: A 100 mL flask was charged with b (0.3 g, 1.0 equiv) and dry THF (50 mL) on anice-water bath, then NaH (0.13 g, 3 equiv) was added in portions carefully. Fiveminutes later, bromide derivative (1.1 equiv) was added drop by drop with constantlystirring. This mixture was kept for 4 h at room temperature. And then 30 mL of waterwas added to this reaction mixture, at the same time, ethyl acetate (50 mL) was alsoadded with stirring for 5 minutes. The obtained upper layer washed with brine for 3times and dried with anhydrous magnesium sulfate. After that, the solvent was evaporated under reduced pressure and the residue was subjected to flash columnchromatography (petroleum ether as eluent) to obtain the corresponding target productc1-c29.
  • 39
  • [ 1997-80-4 ]
  • 2,4,6-trimethyl-N-((3'-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)methyl)benzenesulfonamide [ No CAS ]
  • [ 1613028-93-5 ]
YieldReaction ConditionsOperation in experiment
43% With potassium carbonate In acetonitrile for 2h; Microwave irradiation; Heating; 4.1.3 General method A: Preparation of compounds 4, 6, 7, 12-27 General procedure: A mixture of 11 (1 equiv.), K2CO3 (2 equiv.), and the corresponding alkyl bromide (1 equiv.) in anhydrous acetonitrile (2mL) was heated to 85°C for 2h under microwave irradiation. The white powder was filtered off, the solvent was evaporated, and the mixture was dissolved in ethyl acetate and extracted with brine. The organic phase was separated, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The remaining crude residue was purified by flash chromatography on silica gel (0-100% ethyl acetate/hexanes gradient) to obtain the desired compound.
43% With potassium carbonate In acetonitrile for 2h; Microwave irradiation; Heating; 4.1.3 General method A: Preparation of compounds 4, 6, 7, 12-27 General procedure: A mixture of 11 (1 equiv.), K2CO3 (2 equiv.), and the corresponding alkyl bromide (1 equiv.) in anhydrous acetonitrile (2mL) was heated to 85°C for 2h under microwave irradiation. The white powder was filtered off, the solvent was evaporated, and the mixture was dissolved in ethyl acetate and extracted with brine. The organic phase was separated, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The remaining crude residue was purified by flash chromatography on silica gel (0-100% ethyl acetate/hexanes gradient) to obtain the desired compound.
  • 40
  • [ 1997-80-4 ]
  • 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol [ No CAS ]
  • (2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-1-(3-(trifluoromethyl)phenethyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h; Sealed tube; 5 (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(3-(trifluoromethyl)phenethyl)piperidine-3,4,5-triol K2CO3 (210 mg, 1.52 mmol) was added to a solution of (2R,3R,4R,5S)-3,4,5- tris(benzyloxy)-2-((benzyloxy)methyl)piperidine (100 mg, 0.19 mmol) and 1-(2-bromoethyl)- 3-(trifluoromethyl)benzene (240 mg, 0.95 mmol) in DMF (5 mL) in a sealed tube. The mixture was stirred at 80 °C for 18 h, and cooled to ambient temperature. The reaction mixture was poured into ice water (30 mL) and extracted with EtOAc (3 × 20 mL). The combined organic layer was washed with water (2 × 20 mL), separated, dried over Na2SO4. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified on silica gel flash chromatography affording (2R,3R,4R,5S)-3,4,5-tris(benzyloxy)-2- ((benzyloxy)methyl)-1-(3-(trifluoromethyl)phenethyl)piperidine as a white solid (70 mg, 53%). ESI MS m/z 696.33 [M + H]+.
  • 41
  • [ 1997-80-4 ]
  • 2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol [ No CAS ]
  • (2R,3R,4R,5S)-2-(hydroxymethyl)-1-(3-(trifluoromethyl)phenethyl)piperidine-3,4,5-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 80 °C / Sealed tube 2: boron trichloride / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
  • 42
  • [ 1997-80-4 ]
  • (E)-3,4,5-trimethoxy-cinnamic acid [ No CAS ]
  • (E)-4-hydroxy-3,5-dimethoxycinnamic acid 3-(trifluoromethyl)phenethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With sodium carbonate; potassium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide at 0 - 20℃; for 24h;
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