N-methyl-tetrafluorophthalimide
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With sulfuric acid; benzyltriethylammonium bromide at 45 - 50℃; for 15h; Temperature; | 95.7% |
octafluoro-1,3-dihydroisobenzofuran
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Heating; | 94% |
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With sulfuric acid; cetyltrimethylammonim bromide at 110℃; for 8h; | 88.6% |
With sulfuric acid In water | 67% |
perfluorobenzocyclobutenedione
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: perfluorobenzocyclobutenedione With bromine at 130℃; for 17.5h; Stage #2: With hydrogenchloride for 120h; Further stages.; | 86% |
Stage #1: perfluorobenzocyclobutenedione With antimony pentafluoride at 130℃; for 4.5h; Stage #2: With hydrogenchloride Further stages.; | 70% |
perfluorobenzocyclobutene
A
perfluorobenzocyclobutenedione
B
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: perfluorobenzocyclobutene With antimony pentafluoride; silica gel at 70℃; for 5h; Stage #2: With hydrogenchloride Further stages.; | A 86% B 7% |
perfluorobenzocyclobutene
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With antimony pentafluoride; trifluoroacetic acid at 95℃; for 28h; | 85% |
Conditions | Yield |
---|---|
In water | 82% |
With hydrogenchloride In water |
hexachloro-phthalide
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With hydrogenchloride; potassium fluoride In tetrahydrofuran; sulfolane | 81% |
carbon monoxide
perfluorobenzocyclobutenone
A
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: carbon monoxide; perfluorobenzocyclobutenone With antimony pentafluoride at 20℃; under 760.051 Torr; for 3h; Stage #2: With hydrogenchloride; water at 0℃; | A 10 %Spectr. B 67% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 6h; | 65% |
With nitric acid |
Perfluoro(1-ethylindan)
A
perfluoro(3-methyl-1-oxoisochromene-4-carboxylic acid)
B
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: perfluoro-1-ethylindane With antimony pentafluoride; silica gel at 90 - 130℃; for 13h; Stage #2: With hydrogenchloride Further stages.; | A 39% B 36% |
perfluorobenzocyclobutenone
A
6-trifluoromethyl-2,3,4,5-tetrafluorobenzoic acid
B
perfluoro-2-acetyl-2'-methylbenzophenone
C
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: perfluorobenzocyclobutenone With antimony pentafluoride at 120℃; for 6.5h; Stage #2: With hydrogenchloride Further stages.; | A 18% B 16% C 0.35 g |
perfluorobenzocyclobutene
trifluoroacetic anhydride
A
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Stage #1: perfluorobenzocyclobutene; trifluoroacetic anhydride With antimony pentafluoride at 20℃; for 75h; Sealed tube; Stage #2: With hydrogenchloride; water at 0℃; | A 14% B n/a |
hexafluoro-1,4-naphthoquinone
A
2-hydroxy-3,5,6,7,8-pentafluoro-1,4-naphthoquinone
B
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 80℃; for 20h; Mechanism; | A 0.25 g B 0.33 g |
octafluoronaphthalene
A
2-hydroxy-3,5,6,7,8-pentafluoro-1,4-naphthoquinone
B
2,3,4,5-tetrafluorobenzoic acid
C
3,4,5,6-tetrafluorophthalic acid
D
2-(heptafluoronaphthalen-1-yloxy)pentafluoro-1,4-naphthoquinone
E
2,3,4,5-tetrafluoro-6-(fluoromethyl)phenylglyoxylic acid
F
1-oxoperfluoro-1,2-dihydronaphthalene
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 100℃; for 30h; Product distribution; Mechanism; var. conc.; | A 0.38 g B 0.30 g C 0.65 g D 0.05 g E 0.21 g F 0.30 g |
1-perfluoronaphthol
A
hexafluoro-1,4-naphthoquinone
B
2-hydroxy-3,5,6,7,8-pentafluoro-1,4-naphthoquinone
C
2,3,4,5-tetrafluorobenzoic acid
D
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 80℃; for 20h; Product distribution; Mechanism; var. conc., var. temp.; | A 0.94 g B 0.21 g C 0.24 g D 1.02 g |
1,3,4,5,6,7,8-heptafluoro-2-naphthol
A
2,3,4,5-tetrafluorobenzoic acid
B
3,4,5,6-tetrafluorophthalic acid
C
2,3,4,5-tetrafluoro-6-(fluoromethyl)phenylglyoxylic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 100℃; for 30h; Product distribution; Mechanism; var. conc., var. temp.; | A 0.36 g B 1.32 g C 0.24 g |
Conditions | Yield |
---|---|
(hydrolysis); | |
In water | |
hydrolysis; | |
hydrolysis; | |
With sodium hydroxide; zinc |
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With potassium permanganate In acetone |
1,3-Dihydroxyhexafluornaphthalin
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With nitric acid Heating; |
3,4,5,6,7,8-Hexafluoro-4-nitro-4H-naphthalen-1-one
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With nitric acid |
Conditions | Yield |
---|---|
With antimony pentafluoride; silica gel at 85 - 180℃; for 9h; Title compound not separated from byproducts; |
hexafluoro-1,3-indanedione
C
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With antimony pentafluoride at 130℃; for 2h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 34 percent / SiO2; SbF5 / 4.5 h / 70 - 75 °C 2: SbF5 / 2 h / 130 °C View Scheme |
4,5,6,7-tetrachloro-1,1,3,3-tetrafluoro-1,3-dihydroisobenzofuran
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / potassium fluoride / tetrahydrothiophene 1,1-dioxide / 1.5 h / 210 - 220 °C 2: 94 percent / sulphuric acid / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HNO3 / -10 °C 2: HNO3 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: aq. KMnO4 / acetone View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 160 - 170 °C 2: (hydrolysis) View Scheme |
dmap
trimethylsilyl trifluoromethanesulfonate
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
In chlorobenzene for 24h; Heating; | 99% |
Conditions | Yield |
---|---|
With ammonium hydroxide at 180℃; for 2.5h; Autoclave; Green chemistry; | 97.2% |
With ammonia at 179.99℃; for 1h; pH=1.94; Temperature; | 90% |
In tributyl-amine at 130℃; for 4h; | 81.6% |
Conditions | Yield |
---|---|
With thionyl chloride at 90℃; for 14h; | 97% |
With thionyl chloride | 94% |
With acetyl chloride |
3,4,5,6-tetrafluorophthalic acid
4-amino-3,5,6-trifluorophthalic acid
Conditions | Yield |
---|---|
With ammonia at 110℃; for 100h; Autoclave; | 95% |
Conditions | Yield |
---|---|
With water In benzene at 20 - 80℃; | 95% |
3,4,5,6-tetrafluorophthalic acid
3,4,5,6-tetrafluorophthaloyl dichloride
Conditions | Yield |
---|---|
With phosphorus pentachloride at 180℃; for 2h; | 94% |
With thionyl chloride; N,N-dimethyl-formamide for 18h; Heating; | |
With thionyl chloride; N,N-dimethyl-formamide for 24h; Inert atmosphere; Schlenk technique; Reflux; | |
With thionyl chloride for 48h; Schlenk technique; Reflux; |
dibutyl ether
3,4,5,6-tetrafluorophthalic acid
2,3,4,5-tetrafluorobenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; dimethyl sulfoxide; triethylamine In water; toluene | 94% |
Conditions | Yield |
---|---|
In neat (no solvent) at 110 - 120℃; for 2h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With methanesulfonic acid at 90℃; for 48h; | 91% |
3,4,5,6-tetrafluorophthalic acid
2,4,5-trifluoro-3-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 3,4,5,6-tetrafluorophthalic acid With sodium hydroxide In water at 90℃; for 9h; Stage #2: With hydrogenchloride; tri-n-propylamine In water at 140℃; under 7500.75 Torr; for 7h; pH=1; Temperature; | 90.35% |
Conditions | Yield |
---|---|
With ammonium hydroxide at 250℃; for 0.416667h; Temperature; Time; Autoclave; Green chemistry; | 90.1% |
3,4,5,6-tetrafluorophthalic acid
A
1,2,3,4-tetrafluorobenzene
B
2,3,4,5-tetrafluorobenzoic acid
Conditions | Yield |
---|---|
With ammonium hydroxide at 190℃; for 2h; Temperature; Time; Autoclave; Green chemistry; | A 10.5% B 86.1% |
With ammonium hydroxide at 240℃; for 0.666667h; Temperature; Time; Autoclave; Green chemistry; | A 82% B 8.1% |
3,4,5,6-tetrafluorophthalic acid
isopropylamine
isopropylammonium tetrafluorohydrogenphthalate
Conditions | Yield |
---|---|
In water at 20℃; for 0.166667h; | 84% |
3,4,5,6-tetrafluorophthalic acid
N1-methylbenzene-1,2-diamine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N1-methylbenzene-1,2-diamine hydrochloride With polyphosphoric acid at 80 - 85℃; for 0.25h; Green chemistry; Stage #2: 3,4,5,6-tetrafluorophthalic acid With polyphosphoric acid at 80 - 150℃; Green chemistry; | 84% |
3,4,5,6-tetrafluorophthalic acid
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane at 25℃; electroreduction (divided cells, lead plates, 0.20 A); | 83% |
Conditions | Yield |
---|---|
With acetic acid at 130℃; for 10h; Temperature; | 79.1% |
3,4,5,6-tetrafluorophthalic acid
manganese (II) acetate tetrahydrate
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In water for 0.005h; | 78% |
Conditions | Yield |
---|---|
In water Boiling of stoich. amts. of the starting materials in H2O until a clear soln. is obtained.; Filtn., isolation by evapn. under vac., elem. anal.; | 76% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 120℃; Sealed tube; | 76% |
3,4,5,6-tetrafluorophthalic acid
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
In methanol for 0.25h; | 75% |
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