Conditions | Yield |
---|---|
With oxygen; acetic acid; [Pd{N,N'-di(2,6-di-iPrC6H3)dihydroimidazol-2-yl}(OAc)2(H2O)] In toluene at 60℃; for 12h; | 99% |
With (1,3-diarylimidazol-2-ylidene)-based Pd; oxygen; acetic acid In toluene at 60℃; for 12h; | 99% |
With [(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine)RuCl2(PPh3)]; potassium tert-butylate; acetone In methanol at 56℃; under 750.075 Torr; for 0.166667h; Catalytic behavior; Oppenauer Oxidation; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With oxygen; silver fluoride In N,N-dimethyl-formamide at 50℃; for 3h; Molecular sieve; | 96% |
m-trifluoromethylphenyl iodide
acetic anhydride
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); N-ethyl-N,N-diisopropylamine; lithium chloride In N,N-dimethyl-formamide at 100℃; for 5h; | 94% |
Conditions | Yield |
---|---|
With potassium fluoride; oxygen In N,N-dimethyl-formamide at 50℃; for 18h; Molecular sieve; | 92% |
2-methyl-2-(3-(trifluoromethyl)phenyl)-1,3-dithiolane
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With iodosylbenzene In dichloromethane at 20℃; for 1.41667h; | 85% |
Conditions | Yield |
---|---|
With acetic anhydride In tetrahydrofuran; toluene at -15 - 20℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere; | 81.3% |
3-bromo-1-trifluoromethylbenzene
acetyl chloride
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
Stage #1: 3-bromo-1-trifluoromethylbenzene With trifluoroacetic acid; cobalt(II) bromide; zinc; zinc dibromide In acetonitrile at 20℃; Stage #2: acetyl chloride In acetonitrile at 20℃; | 80% |
Stage #1: 3-bromo-1-trifluoromethylbenzene With cobalt(II) bromide; zinc dibromide In acetonitrile at 20℃; Electrochemical reaction; Stage #2: acetyl chloride With bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; Negishi coupling reaction; | 76% |
(i) Mg, (ii) CdCl2, (iii) /BRN= 605303/; Multistep reaction; |
(meta-(trifluoromethyl)phenyl)boronic acid
acetonitrile
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave; | 77% |
1-(3-aminophenyl)ethanone
(trifluoromethyl)trimethylsilane
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
Stage #1: 1-(3-aminophenyl)ethanone With tert.-butylnitrite; toluene-4-sulfonic acid In acetonitrile at 20℃; for 0.5h; Sandmeyer Reaction; Inert atmosphere; Stage #2: (trifluoromethyl)trimethylsilane With copper(I) thiocyanate; caesium carbonate In acetonitrile at 20℃; for 0.202833h; Sandmeyer Reaction; Inert atmosphere; | 74% |
3-bromo-1-trifluoromethylbenzene
acetic anhydride
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
Stage #1: 3-bromo-1-trifluoromethylbenzene With isopropyl magnesium chloride; lithium chloride In tetrahydrofuran at 70℃; under 50.03 Torr; for 3.5h; Inert atmosphere; Stage #2: acetic anhydride at 0 - 40℃; Inert atmosphere; | 73.8% |
(i) Mg, Et2O, (ii) /BRN= 385737/; Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride In water; N,N-dimethyl-formamide | 73% |
Conditions | Yield |
---|---|
With manganese(II) bromide; water; lithium perchlorate; copper dichloride In acetonitrile at 60℃; for 8h; Wacker-Tsuji Olefin Oxidation; Sealed tube; Inert atmosphere; Electrochemical reaction; regioselective reaction; | 72% |
3-bromo-1-trifluoromethylbenzene
acetic anhydride
A
α,α,α-trifluorotoluene
B
3,3'-bis(trifluoromethyl)biphenyl
C
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With 3-chloroprop-1-ene; cobalt(II) bromide; zinc; trifluoroacetic acid In acetonitrile for 6h; | A 8 % Chromat. B 2 % Chromat. C 71% |
With 3-chloroprop-1-ene; cobalt(II) bromide; zinc; trifluoroacetic acid In acetonitrile for 6h; | A 11 % Chromat. B 1 % Chromat. C 74 % Chromat. |
ethyl 2-cyanoacetate
(meta-(trifluoromethyl)phenyl)boronic acid
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 90℃; for 8h; | 71% |
3-trifluormethylisopropylbenzene
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; oxygen In benzonitrile at 100℃; for 20h; | 65% |
3-<(trimethylsilyl)ethynyl>benzotrifluoride
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With iron(III) sulphate monohydrate; acetic acid at 95℃; for 40h; regioselective reaction; | 65% |
Conditions | Yield |
---|---|
56% | |
Multi-step reaction with 2 steps 1.1: NaNO2; aq. HCl / 0.33 h / -5 - 0 °C 1.2: CuSO4; AcONa*3H2O / aq. HCl / 1.5 h / 0 - 15 °C 2.1: 14.5 g / conc. HCl / 2 h / Heating View Scheme |
(trifluoromethyl)trimethylsilane
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate; cesium fluoride In Isobutyronitrile at 20℃; under 760.051 Torr; for 3h; Chan-Lam-type reaction; Molecular sieve; Inert atmosphere; | 54% |
trifluoromethanesulfonic acid difluoromethyl ether
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
Stage #1: trifluoromethanesulfonic acid difluoromethyl ether With copper(I) thiophene-2-carboxylate; tetrabutylammonium triphenyldifluorosilicate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: (3-acetylphenyl)(mesityl)iodonium trifluoromethanesulfonate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; | 54% |
(E)-acetaldoxime
copper(II) sulphate hydrate
3-trifluoromethylaniline
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With sodium nitrite In water | 51.5% |
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; copper diacetate In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 16h; Inert atmosphere; | 50% |
pentacarbonyl(methoxymethylcarbene)chromium(0)
(meta-(trifluoromethyl)phenyl)boronic acid
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
Stage #1: pentacarbonyl(methoxymethylcarbene)chromium(0); [3-(trifluoromethyl) phenyl] boronic acid With trifuran-2-yl-phosphane; palladium diacetate; diisopropylamine In toluene at 90℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 60℃; for 2h; Inert atmosphere; | 35% |
2-cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium triflate
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With 2,4,6-trimethyl-pyridine; copper diacetate In ethyl acetate at 20℃; for 20h; Inert atmosphere; | 30% |
methyl magnesium iodide
3-trifluoromethylbenzonitrile
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With diethyl ether anschliessend Behandeln mit wss. HCl; |
3-trifluoromethylbenzonitrile
methylmagnesium bromide
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With diethyl ether anschliessend Behandeln mit wss. HCl; |
Conditions | Yield |
---|---|
With diethyl ether; dimethylcadmium |
1-(1-Methoxy-vinyl)-3-trifluoromethyl-benzene
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With sulfuric acid In water at 25℃; Rate constant; |
1-(1,1-Dimethoxy-ethyl)-3-trifluoromethyl-benzene
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With hydrogen bromide at 25℃; Rate constant; var. conc. of water; | |
With hydrogen bromide; bromine In chlorobenzene at 25℃; Rate constant; |
Conditions | Yield |
---|---|
In benzene Rate constant; Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0 - 20℃; | 100% |
Stage #1: 3'-(trifluoromethyl)acetophenone With C107H90Cl2N10P4Ru2(2+)*2Cl(1-) In isopropyl alcohol at 82℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium isopropoxide In isopropyl alcohol for 2h; Catalytic behavior; Inert atmosphere; | 99% |
With palladium; hydrogen In methanol at 30℃; for 20h; | 99% |
3'-(trifluoromethyl)acetophenone
3-trifluoromethylbenzoylformaldehyde
Conditions | Yield |
---|---|
With water; hydrogen bromide; dimethyl sulfoxide at 20 - 70℃; | 100% |
With selenium(IV) oxide In methanol | |
Multi-step reaction with 2 steps 1: Br2 / acetic acid 2: DMSO View Scheme | |
With iodine; dimethyl sulfoxide at 90℃; | |
With selenium(IV) oxide In 1,4-dioxane; water at 115℃; for 12h; Inert atmosphere; |
3'-(trifluoromethyl)acetophenone
ethylhydrazine carboxylate
ethyl 2-(1-(3-(trifluoromethyl)phenyl)ethylidene)hydrazinecarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 100% |
With toluene-4-sulfonic acid In benzene for 4h; Heating; | 100% |
3'-(trifluoromethyl)acetophenone
1-(3-(trifluoromethyl)phenyl)ethanone oxime
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 95℃; | 100% |
With pyridine; hydroxylamine hydrochloride at 80℃; for 0.25h; | 96% |
With hydroxylamine hydrochloride; sodium hydroxide In ethanol pH=8; Reflux; | 95.5% |
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene | 100% |
3'-(trifluoromethyl)acetophenone
Conditions | Yield |
---|---|
With potassium formate; Cp*IrCl[(S,S)-(C2H5)2CHCH2SO2dpen]; tetrabutylammomium bromide In water at 50℃; for 24h; Inert atmosphere; | 100% |
With formic acid; C24H28ClN2O2PolRuS; triethylamine In dichloromethane at 40℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
3'-(trifluoromethyl)acetophenone
(R)-1-(3-trifluoromethylphenyl)ethanol
Conditions | Yield |
---|---|
With potassium tert-butylate; hydrogen; RuCl2[(S)-XylHexaPHEMP][(S)-1,1-dianisyl-2-iPr-1,2-Et(NH2)2] In isopropyl alcohol; tert-butyl alcohol at 20℃; under 6205.94 Torr; for 0.683333h; | 99% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C45H58NP; potassium tert-butylate; hydrogen In propan-1-ol at 25 - 30℃; under 4560.31 Torr; for 0.166667h; Autoclave; optical yield given as %ee; enantioselective reaction; | 99% |
With [Fe(II)(3-ethyl-3-isocyanopentane)2((5S,8S,14aS,18aS)-5,8-diphenyl-5,6,7,8,13,14,14a,15,16,17,18,18a,19,20-tetradecahydrotribenzo[b,f,l][1,4]diaza[8,11]diphosphacyclotetradecine)](BF4)2; isopropyl alcohol; sodium t-butanolate at 60℃; for 1h; Glovebox; enantioselective reaction; | 99.7% |
Conditions | Yield |
---|---|
With bromine In diethyl ether for 3h; Ambient temperature; | 99% |
With bromine In chloroform for 1.5h; Ambient temperature; | 92.9% |
With aluminum (III) chloride; bromine In diethyl ether at 20℃; for 1.5h; | 92% |
3'-(trifluoromethyl)acetophenone
1-(3-(trifluoromethyl)phenyl)ethan-1-amine
Conditions | Yield |
---|---|
Stage #1: 3'-(trifluoromethyl)acetophenone With aluminium(III) triflate; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 1,2-bis-(diphenylphosphino)ethane In dodecane; toluene at -5℃; under 4500.45 Torr; for 0.5h; Autoclave; Stage #2: With hydrogen In dodecane; toluene at 140℃; under 30003 Torr; for 16h; Acidic conditions; chemoselective reaction; | 99% |
With aluminium(III) triflate; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; hydrogen; 1,2-bis-(diphenylphosphino)ethane at 140℃; for 16h; Autoclave; | 99% |
With 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; ammonium formate In methanol at 80℃; for 12h; Inert atmosphere; chemoselective reaction; | 82% |
3'-(trifluoromethyl)acetophenone
(S)-1-(3-trifluoromethylphenyl)ethanol
Conditions | Yield |
---|---|
With D-glucose In aq. phosphate buffer at 25℃; for 24h; pH=7.0; stereoselective reaction; | 99% |
With ethanol; Rhodococcus species-1 alcohol dehydrogenase; NAD; bovine serum albumin; yeast alcohol dehydrogenase; yeast aldehyde dehydrogenase at 30℃; for 12h; pH=7.5; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee; | 98% |
With formic acid; chloro {[(1S,2S)-(+)-2-amino-1,2-diphenylethyl]((4-toluenesulfonyl)amido)(p-cymene)}ruthenium(ll) In N,N-dimethyl-formamide at 50℃; for 27h; Reagent/catalyst; Temperature; Time; Solvent; Inert atmosphere; Industrial scale; enantioselective reaction; | 98% |
trimethylsulfoxonium iodide
3'-(trifluoromethyl)acetophenone
2-methyl-2-(3-trifluoromethylphenyl)-oxirane
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20℃; | 99% |
3'-(trifluoromethyl)acetophenone
A
(R)-1-(3-trifluoromethylphenyl)ethanol
B
triethylamine
Conditions | Yield |
---|---|
A 99% B n/a |
isopropyl alcohol
3'-(trifluoromethyl)acetophenone
(R)-1-(3-trifluoromethylphenyl)ethanol
Conditions | Yield |
---|---|
In argon | 98.7% |
Conditions | Yield |
---|---|
Stage #1: dimethyl sulfate With p-propoxybenzyl sulfide at 90℃; for 2h; Stage #2: 3'-(trifluoromethyl)acetophenone With potassium hydroxide In dimethyl sulfoxide at 50℃; for 4h; | 98.6% |
2-Aminobenzyl alcohol
3'-(trifluoromethyl)acetophenone
2-(3-(trifluoromethyl)phenyl)quinoline
Conditions | Yield |
---|---|
With potassium hydroxide; Grubbs catalyst first generation In 1,4-dioxane at 80℃; for 1h; | 98% |
With silver; potassium hydroxide In toluene at 80℃; for 24h; | 81% |
With dimanganese decacarbonyl; sodium hydroxide In toluene at 110℃; for 2h; Friedlaender Quinoline Synthesis; Inert atmosphere; Glovebox; Sealed tube; | 80% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; magnesium bromide; (1S,2R,4R,1'R,2'R,1''S,2''R,4''R)-N-{trans-2'-[2''-hydroxy-7'',7''-dimethylbicyclo[2.2.1]hept-1''-ylmethylsulfonamino]cyclohexyl}-2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethanesulfonamide In toluene at 0℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 25℃; Claisen-Schmidt Condensation; | 97.1% |
1-methyl-1H-indole-2,3-dione
3'-(trifluoromethyl)acetophenone
1-methyl-3-hydroxy-3-(2-(3-trifluoromethylphenyl)-2-oxoethyl)indolin-2-one
Conditions | Yield |
---|---|
With piperidine In ethanol at 20℃; for 6h; | 97% |
Conditions | Yield |
---|---|
Stage #1: 3'-(trifluoromethyl)acetophenone With sodium hydroxide In ethanol; water at 20℃; for 0.0833333h; Claisen-Schmidt Condensation; Stage #2: 2,6-dimethoxybenzaldehyde at 20℃; Claisen-Schmidt Condensation; | 97% |
Conditions | Yield |
---|---|
In ethanol at 0 - 20℃; for 72h; Molecular sieve; Inert atmosphere; Sealed tube; | 96% |
methyl magnesium iodide
3'-(trifluoromethyl)acetophenone
α,α-dimethyl-3-(trifluoromethyl)benzenemethanol
Conditions | Yield |
---|---|
95% |
(2-ethylbutyl)magnesium bromide
3'-(trifluoromethyl)acetophenone
(+)-(R)-4-ethyl-2-(3-(trifluoromethyl)phenyl)hexan-2-ol
Conditions | Yield |
---|---|
With copper(I) bromide dimethylsulfide complex; (S,R)-revJosiphos In diethyl ether; tert-butyl methyl ether at -78℃; for 0.25h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 95% |
ethane-1,2-dithiol
3'-(trifluoromethyl)acetophenone
2-methyl-2-(3-(trifluoromethyl)phenyl)-1,3-dithiolane
Conditions | Yield |
---|---|
at 20℃; | 95% |
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With dimethyl zinc(II) In toluene at 20℃; for 0.5h; Stage #2: 3'-(trifluoromethyl)acetophenone In toluene at 20℃; for 24h; | 94% |
Stage #1: phenylacetylene With tetrabutyl-ammonium chloride; potassium hydroxide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Molecular sieve; Stage #2: 3'-(trifluoromethyl)acetophenone In tetrahydrofuran at 20℃; for 72h; Inert atmosphere; Molecular sieve; Stage #3: With water; ammonium chloride In tetrahydrofuran Inert atmosphere; Molecular sieve; | 83% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate; tin(ll) chloride In water at 20℃; for 24h; | 94% |
4-methoxy-aniline
3'-(trifluoromethyl)acetophenone
4-methoxy-N-(1-(3-(trifluoromethyl)phenyl)ethyl)aniline
Conditions | Yield |
---|---|
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; C89H110IrN2O6PS; hydrogen In toluene at 35℃; under 3750.38 Torr; for 24h; Molecular sieve; optical yield given as %ee; enantioselective reaction; | 94% |
1-(5-bromo-2-iodophenyl)ethanone
3'-(trifluoromethyl)acetophenone
7-bromo-3-(3-(trifluoromethyl)phenyl)naphthalen-1-ol
Conditions | Yield |
---|---|
With copper(l) iodide; 1,10-Phenanthroline; sodium t-butanolate In toluene at 20℃; for 4.5h; Inert atmosphere; Sealed tube; | 94% |
The 3'-(Trifluoromethyl)acetophenone with cas registry number of 349-76-8 is a kind of clear colourless to very slightly yellow liquid which is also known as 3-Acetylbenzotrifluoride. Both its systematic name and IUPAC name are the same which is called 1-[3-(trifluoromethyl)phenyl]ethanone. It has EINECS registry number of 206-490-4. This chemical belongs to the following categories: Multisubstituted Benzene; Carbonyl Compounds; Aromatic Acetophenones & Derivatives (substituted); Organics; Benzene series.
The physical properties about this chemical are: (1)ACD/LogP: 2.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.72; (4)ACD/LogD (pH 7.4): 2.72; (5)ACD/BCF (pH 5.5): 68.82; (6)ACD/BCF (pH 7.4): 68.82; (7)ACD/KOC (pH 5.5): 719.51; (8)ACD/KOC (pH 7.4): 719.51; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.446; (13)Molar Refractivity: 41.26 cm3; (14)Molar Volume: 154.4 cm3; (15)Surface Tension: 26.2 dyne/cm; (16)Density: 1.218 g/cm3; (17)Flash Point: 83.9 °C; (18)Enthalpy of Vaporization: 43.52 kJ/mol; (19)Boiling Point: 199 °C at 760 mmHg; (20)Vapour Pressure: 0.349 mmHg at 25°C ; (21)Refractive index: n20/D 1.4611(lit.).
Preparation of 3'-(Trifluoromethyl)acetophenone: it can be prepared by 1-(3-trifluoromethyl-phenyl)-ethanol with reagent CsSO4F and solvent acetonitrile at temperature of 30 - 35 ℃. The reaction time is about 1 hour with 88% yield.
Uses of 3'-(Trifluoromethyl)acetophenone: it can produce 2-bromo-1-(3-trifluoromethyl-phenyl)-ethanone with reagents Br2 and solvent CHCl3 at ambient temperature. The reaction time is 1.5 hours with yield of 92.9%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Therefore, wear suitable protective clothing, gloves and eye/face protection during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)c1cccc(C(=O)C)c1;
(2)InChI: InChI=1/C9H7F3O/c1-6(13)7-3-2-4-8(5-7)9(10,11)12/h2-5H,1H3;
(3)InChIKey: ABXGMGUHGLQMAW-UHFFFAOYAB
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