Conditions | Yield |
---|---|
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen; sodium triethylborohydride In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique; | 100% |
With hydrazine hydrate In ethanol at 40℃; for 0.5h; | 99% |
With LaCu0.67Si1.33; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 54h; Autoclave; | 99% |
Conditions | Yield |
---|---|
nickel In methanol for 1h; Heating / reflux; | 100% |
With hydrogen; nickel In methanol at 20℃; under 3750.38 Torr; for 2h; | 75% |
Conditions | Yield |
---|---|
With C24H32N2*ClCu; ammonia; potassium carbonate In 1-methyl-pyrrolidin-2-one; methanol at 90℃; under 5171.62 Torr; for 24h; Inert atmosphere; | 95% |
With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 50℃; for 24h; | 91% |
Stage #1: p-trifluoromethylphenyl bromide With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 90% |
Conditions | Yield |
---|---|
With ammonium hydroxide; caesium carbonate In water for 1h; Reflux; Green chemistry; | 92% |
With ammonium hydroxide; caesium carbonate In water for 1h; Catalytic behavior; Reflux; | 92% |
With ammonium hydroxide; caesium carbonate In acetonitrile for 1h; Reflux; Green chemistry; | 91% |
Conditions | Yield |
---|---|
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction; | 92% |
With C36H44CuN8(1+)*BF4(1-) In water; toluene at 100℃; for 20h; Sealed tube; chemoselective reaction; | 64% |
With sodium tetrahydroborate In methanol; water at 20℃; for 0.333333h; Green chemistry; | > 99 %Chromat. |
With sodium tetrahydroborate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol; water at 20℃; for 0.166667h; | |
With sodium tetrahydroborate In water at 20℃; for 0.416667h; Green chemistry; | > 99 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: 4-chlorobenzotrifluoride With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 90℃; for 18h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 88% |
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation; | 86% |
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; ammonia; sodium t-butanolate In 1,4-dioxane at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; | 62% |
4-trifluoromethylcyclohexanone oxime
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With Pd(OH)x/LDH In N,N-dimethyl acetamide at 150℃; for 1h; Schlenk technique; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 130℃; for 24h; | A 79% B n/a |
4-trifluoromethylphenylboronic acid
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With O-(2,4-dinitrophenyl)hydroxylamine In toluene at 80℃; for 96h; Inert atmosphere; | 78% |
With copper(I) oxide; ammonium hydroxide; oxygen; sodium hydroxide In water at 25℃; for 24h; | 70% |
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 5h; Reflux; | 57% |
4-(triethylsiloxy)-4-(trifluoromethyl)-2,5-cyclohexadien-1-one
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With glycine ethyl ester hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Heating; | 73% |
(trifluoromethyl)trimethylsilane
4-bromo-aniline
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; sodium dodecyl-sulfate; cesium fluoride In toluene at 110℃; for 12h; Inert atmosphere; | 71% |
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 100℃; Sealed tube; | 69% |
Togni's reagent II
aniline
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 75℃; for 6h; Schlenk technique; Inert atmosphere; | A 20% B 66% |
With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2h; Reagent/catalyst; Solvent; Temperature; Overall yield = 89 %; | A 20% B 61% |
With potassium carbonate; nickel(II) hydroxide In dimethyl sulfoxide at 35℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere; | A 20% B 49% |
Conditions | Yield |
---|---|
With [RuCl2(2-(diphenylphosphino)-N-((6-((diphenylphosphino)methyl)pyridin-2-yl)methyl)ethan-1-amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 20h; Catalytic behavior; Autoclave; chemoselective reaction; | 65% |
2,5-dimethyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrrole
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With trifluoroacetic acid for 48h; Reflux; | 56% |
iodotrifluoromethane
aniline
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction; | A 34% B 54% |
With sulfuric acid; dihydrogen peroxide; iron(II) sulfate; dimethyl sulfoxide In water at 40 - 50℃; for 0.333333h; | A 7.2 %Spectr. B 8.5 %Spectr. |
With dihydrogen peroxide; iron(II) sulfate In water; dimethyl sulfoxide | A 13 %Spectr. B 22 %Spectr. |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; regioselective reaction; | A 24% B 54% |
Conditions | Yield |
---|---|
With vanadium(V) oxytrifluoride; trifluoroacetic acid In dichloromethane; ethyl acetate at -30℃; for 0.166667h; | A 52% B 75 mg C 220 mg |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere; | A 23% B 44% |
3,7-dinitro-Se-(trifluoromethyl)dibenzoselenophenium triflate
aniline
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Title compound not separated from byproducts; | A 16 % Spectr. B 39% |
In N,N-dimethyl-formamide for 0.5h; Ambient temperature; Title compound not separated from byproducts; | A 16 % Spectr. B 39 % Spectr. |
Umemoto's reagent
aniline
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 5h; Title compound not separated from byproducts; | A 15% B 37% |
In N,N-dimethyl-formamide at 80℃; for 7h; | A 18% B 39 % Spectr. |
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere; | A 2% B 5% |
aniline
S-(Trifluoromethyl)-7-nitrodibenzothiophenium-3-sulfonate
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 0.5h; | A 18 % Spectr. B 37% |
In N,N-dimethyl-formamide at 80℃; for 0.5h; | A 18% B 37 % Spectr. |
In N,N-dimethyl-formamide at 80℃; for 0.5h; Product distribution; other temperature; |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Overall yield = 65 %; regioselective reaction; | A n/a B 37% C n/a |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 30℃; for 3h; Inert atmosphere; | A 17% B 37% |
Bromotrifluoromethane
aniline
A
4-trifluoromethylphenylamine
B
2-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
With α-picoline; sodium metabisulfite; sulfur dioxide; zinc In N,N-dimethyl-formamide at 20℃; under 2250.2 - 3750.3 Torr; for 2h; Product distribution; other alkylating reagents, other method, other pressure, temp.; various substrates; | A 20% B 36% |
With α-picoline; sodium metabisulfite; sulfur dioxide; zinc In N,N-dimethyl-formamide at 20℃; under 2250.2 - 3750.3 Torr; for 2h; also with NaS2O4; | A 20% B 36% |
With sulfur dioxide; zinc In N,N-dimethyl-formamide under 2250.2 - 3750.3 Torr; for 2h; Ambient temperature; | A 20% B 36% |
1,2-bis(4-(trifluoromethyl)phenyl)hydrazine
β-naphthol
A
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
In neat (no solvent) at 120℃; Inert atmosphere; | A n/a B 34% |
Conditions | Yield |
---|---|
Stage #1: 4-trifluoromethylbenzoic acid With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; for 0.0583333h; Schmidt Reaction; Flow reactor; Stage #2: With water In methanol; chloroform at 20℃; Schmidt Reaction; Flow reactor; | 24% |
tert-butyl 2-(2,6-dimethylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate
A
4-trifluoromethylphenylamine
B
3′,5′-dimethyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine
C
3,5-dimethyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine
D
2,6-Dimethyl-4'-(trifluoromethyl)azobenzene
E
2,6-dimethylaniline
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux; | A 9% B 21% C 18% D 10% E 6% |
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Overall yield = 58 %; regioselective reaction; | A 9% B 21% C 18% D 10% E 6% |
tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate
A
4-trifluoromethylphenylamine
B
6-ethyl-o-toluidine
C
3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine
D
3-ethyl-5-methyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine
E
1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 20℃; for 2h; Inert atmosphere; Reflux; | A 10% B 6% C 10% D 18% E 12% |
With hydrogenchloride In ethanol for 2h; Inert atmosphere; Reflux; Overall yield = 50 %; regioselective reaction; | A 10% B 6% C 10% D 18% E 12% |
4-trifluoromethylphenylamine
Ethyl oxalyl chloride
ethyl 2-oxo-2-((4-(trifluoromethyl)phenyl)amino)acetate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 8h; | 100% |
With triethylamine In tetrahydrofuran at 20℃; | 99% |
With pyridine In dichloromethane at 0 - 20℃; for 43h; Reflux; Inert atmosphere; Schlenk technique; | 96% |
4-trifluoromethylphenylamine
2-iodo-4-(trifluoromethyl)aniline
Conditions | Yield |
---|---|
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane at 20℃; for 2h; | 100% |
With Iodine monochloride In methanol; dichloromethane at 0 - 20℃; | 97% |
With Iodine monochloride In methanol; dichloromethane at 0 - 20℃; for 1h; | 97% |
4-trifluoromethylphenylamine
acetic anhydride
4-(trifluromethyl)acetanilide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; Inert atmosphere; | 100% |
In dichloromethane; water at 25℃; for 1h; Temperature; | 99.3% |
With pyridine at 0 - 20℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
With tert.-butylnitrite; trimethylsilylazide In acetonitrile at 20℃; for 1h; Inert atmosphere; | 100% |
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 2h; Stage #2: With sodium azide In water at 0 - 20℃; | 95% |
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 2h; Stage #2: With sodium azide In water at 0℃; for 2h; | 95% |
4-trifluoromethylphenylamine
benzoyl chloride
N-(4-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; | 100% |
With dmap In dichloromethane at 20℃; Inert atmosphere; | 91% |
With triethylamine In dichloromethane at 0 - 40℃; Inert atmosphere; | 75% |
furfural
4-trifluoromethylphenylamine
1-(furan-2-yl)-N-(4-(trifluoromethyl)phenyl)methanimine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In diethyl ether at 20℃; Molecular sieve; Inert atmosphere; | 100% |
In benzene at 20℃; for 20h; | 70% |
4-trifluoromethylphenylamine
5-triethylsilylfuran-2-carbaldehyde
Conditions | Yield |
---|---|
With 4 A molecular sieve In benzene at 20℃; for 20h; | 100% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine In dichloromethane at 20℃; for 24h; | 98% |
for 0.1h; microwave irradiation; | 92% |
4-trifluoromethylphenylamine
3,4-dihydro-4-oxo-3-(2-chloro-3-pyridyl)-2-quinazolinecarbothioic acid S-p-tolyl ester
3-(2-chloro-pyridin-3-yl)-4-oxo-3,4-dihydro-quinazoline-2-carboxylic acid (4-trifluoromethyl-phenyl)-amide
Conditions | Yield |
---|---|
With silver trifluoroacetate In tetrahydrofuran; toluene at 60℃; for 1.5h; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
4-trifluoromethylphenylamine
potassium thioacyanate
1-(4-(trifluoromethyl)phenyl)thiourea
Conditions | Yield |
---|---|
With hydrogenchloride In water Heating / reflux; | 100% |
(3R)-5-methoxy-3-[(trifluoroacetyl)amino]chromane-8-sulfonyl chloride
4-trifluoromethylphenylamine
2,2,2-trifluoro-N-[(3R)-5-methoxy-8-({[4-(trifluoromethyl)phenyl]amino}sulfonyl)-3,4-dihydro-2H-chromen-3-yl]acetamide
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 8h; | 100% |
4-trifluoromethylphenylamine
propionaldehyde
N-propyl-4-(trifluoromethyl)benzenamine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 18℃; for 0.0833333h; Solvent; Green chemistry; | 100% |
Conditions | Yield |
---|---|
In dichloromethane for 4h; Molecular sieve; | 100% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With p-toluenesulfonic acid monohydrate In 1-methyl-pyrrolidin-2-one at 60℃; for 2h; | 100% |
With toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 60℃; for 2h; | 51% |
furfural
4-trifluoromethylphenylamine
(E)-1-(furan-2-yl)-N-(4-(trifluoromethyl)phenyl)methanimine
Conditions | Yield |
---|---|
In toluene Inert atmosphere; Reflux; Dean-Stark; | 100% |
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
In tetrahydrofuran at 40℃; for 2h; Inert atmosphere; Darkness; | 100% |
4-trifluoromethylphenylamine
benzaldehyde
N-benzylidene-4-(trifluoromethyl)aniline
Conditions | Yield |
---|---|
at 50℃; Condensation; | 99.1% |
In water at 20℃; for 12h; Inert atmosphere; | 95% |
In toluene for 0.5h; Heating; | 84% |
4-trifluoromethylphenylamine
4-nitro-benzoyl chloride
4-nitro-N-(4-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 99% |
With pyridine for 4h; Heating; | 95% |
With pyridine at 20℃; Inert atmosphere; Reflux; | 95% |
4-trifluoromethylphenylamine
potassium thioacyanate
2-amino-6-trifluoromethyl-1,3-benzothiazole
Conditions | Yield |
---|---|
With sodium iodide dichloride at 70℃; for 2h; | 99% |
With 6-methylbenzothiazol-2-ylamine; N,N,N,N,-tetramethylethylenediamine; oxygen; copper(II) bis(trifluoromethanesulfonate) In dimethyl sulfoxide at 100℃; for 24h; regioselective reaction; | 80% |
With bromine In acetic acid for 24h; | 20% |
With bromine; acetic acid for 21h; Ambient temperature; | |
With bromine In acetic acid Cooling with ice; |
Conditions | Yield |
---|---|
With ammonium acetate; hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h; | 99% |
With palladium 10% on activated carbon; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr; for 18h; | 99% |
4-(chlorocarbonyl)pyridine
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 65℃; for 1.58333h; | 99% |
4-trifluoromethylphenylamine
Cp*Ni(PEt3)S(OMe)
Cp*Ni(PEt3)NHC6H4(p-CF3)
Conditions | Yield |
---|---|
In diethyl ether inert atmosphere; stirring (10 min); removal of volatile materials (vac.), crystn. (pentane); | 99% |
4-trifluoromethylphenylamine
5-nitrosalicylic acid
2-hydroxy-5-nitro-N-[4-(trifluoromethyl)phenyl]benzamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; | 99% |
With phosphorus trichloride Microwave irradiation; Reflux; | 76% |
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 3h; Inert atmosphere; | 66.2% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; |
3-Chloropropyl isocyanate
4-trifluoromethylphenylamine
1-(3-chloropropyl)-3-(4-(trifluoromethyl)phenyl)urea
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 99% |
In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 72h; | 87% |
In dichloromethane at 20℃; for 72h; | |
In dichloromethane at 20℃; |
Conditions | Yield |
---|---|
In ethanol Reflux; | 99% |
4-trifluoromethylphenylamine
Conditions | Yield |
---|---|
Stage #1: tetrafluoroboric acid; 4-trifluoromethylphenylamine In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0℃; for 0.283333h; | 99% |
With isopentyl nitrite In ethanol; water at -20 - 20℃; for 1h; Inert atmosphere; | 77% |
With sodium nitrite In water at 0℃; for 0.5h; | 70% |
1. | mmo-sat 10 mg/L | ENMUDM Environmental Mutagenesis. 5 (1983),803. | ||
2. | mmo-esc 10 mg/L | ENMUDM Environmental Mutagenesis. 5 (1983),803. | ||
3. | ipr-mus LD50:101 mg/kg | JMCMAR Journal of Medicinal Chemistry. 17 (1974),900. |
Poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits very toxic fumes of F− and NOx. See also FLUORIDES.
Hazard Codes: T, N, Xi, Xn
Hazard Note: Toxic/Irritant
The Risk Statements information of p-TRIFLUOROMETHYLANILINE:
25: Toxic if swallowed
33: Danger of cumulative effects
36: Irritating to the eyes
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
The Safety Statements information of p-TRIFLUOROMETHYLANILINE:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60: This material and/or its container must be disposed of as hazardous waste
61: Avoid release to the environment. Refer to special instructions safety data sheet
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
RTECS: XU9260000
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