2-Fluoroaniline
2-fluro-4-iodoaniline
Conditions | Yield |
---|---|
With iodine; sodium hydrogencarbonate In water at 60 - 80℃; for 2h; | 77% |
With iodine; sodium hydrogencarbonate In water at 60℃; for 3h; | 76% |
Stage #1: 2-Fluoroaniline With n-butyllithium In diethyl ether; hexane at -78℃; for 1h; Stage #2: With poly[4-(dibutyliodostannyl)butyl]styrene In diethyl ether; hexane at 20℃; for 18h; Stage #3: With Iodine monochloride In diethyl ether; hexane at -78 - 20℃; | 67% |
2-fluro-4-iodoaniline
trimethylsilylacetylene
2-fluoro-4-((trimethylsilyl)ethynyl)aniline
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 21h; Sonogashira Cross-Coupling; Inert atmosphere; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; Inert atmosphere; | 100% |
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 20℃; for 15h; Sonogashira Coupling; | 88% |
4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid
2-fluro-4-iodoaniline
4-(2-fluoro-4-iodophenylamino)-1-methyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid
Conditions | Yield |
---|---|
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity; | 100% |
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4.08333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity; | 100% |
Stage #1: 4-chloro-1-methyl-6-oxo-1,6-dihydro-pyridazine-3-carboxylic acid; 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 4.08333h; Stage #2: With hydrogenchloride In tetrahydrofuran; water Product distribution / selectivity; | 100% |
thiophosgene
2-fluro-4-iodoaniline
2-fluoro-4-iodo-1-isothiocyanatobenzene
Conditions | Yield |
---|---|
In chloroform; water at 20℃; for 16h; | 100% |
In chloroform; water at 20℃; for 16h; | 100% |
In dichloromethane; water at 20℃; | 96.8% |
Conditions | Yield |
---|---|
With acetic anhydride In tetrahydrofuran; toluene at 20℃; | 100% |
2-fluro-4-iodoaniline
sodium O-ethyl dithiocarbonate
6-iodobenzo[d]thiazole-2-thiol
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 95℃; for 5h; | 100% |
2-fluro-4-iodoaniline
2,3,4,-trifluorobenzoic acid
3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzoic acid
Conditions | Yield |
---|---|
With lithium amide In tetrahydrofuran | 99% |
With lithium amide In N,N-dimethyl-formamide Inert atmosphere; | 85% |
With lithium amide In tetrahydrofuran at 45 - 55℃; for 1.25 - 2.5h; Product distribution / selectivity; | 80% |
2-fluro-4-iodoaniline
1-azido-2-fluoro-4-iodobenzene
Conditions | Yield |
---|---|
Stage #1: 2-fluro-4-iodoaniline With trifluoroacetic acid; sodium nitrite at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 1h; | 99% |
Stage #1: 2-fluro-4-iodoaniline With hydrogenchloride; sodium nitrite In water at -5℃; for 0.5h; Stage #2: With sodium azide In water at -5℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With N,N`-dimethylethylenediamine; copper (I) trifluoromethane sulfonate benzene In dimethyl sulfoxide at 120℃; for 16h; | 99% |
copper(I) trifluoromethanesulfonate benzene complex; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 120℃; for 16h; | 99% |
With N,N`-dimethylethylenediamine; copper(I) trifluoromethanesulfonate benzene In dimethyl sulfoxide at 120℃; for 16h; | 99% |
2-fluro-4-iodoaniline
cyclopropanecarboxylic acid chloride
N-(2-fluoro-4-iodophenyl)cyclopropanecarboxamide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; | 99% |
2-fluro-4-iodoaniline
1,1'-carbonyldiimidazole
1-(2-fluoro-4-iodophenyl)urea
Conditions | Yield |
---|---|
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In chloroform at 0 - 20℃; for 4.25h; Stage #2: With ammonia In chloroform; water at 0 - 20℃; for 1.5h; | 98.8% |
With triethylamine In chloroform at 0 - 30℃; for 4h; Inert atmosphere; | |
With triethylamine In chloroform at 0 - 20℃; for 4.25h; |
2-fluro-4-iodoaniline
2,5-hexanedione
1-(2-fluoro-4-iodophenyl)-2,5-dimethyl-1H-pyrrole
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In toluene for 1h; Heating / reflux; | 98% |
With toluene-4-sulfonic acid In toluene at 110℃; for 1h; | 49% |
With p-toluenesulfonic acid monohydrate In toluene at 110℃; for 1h; Dean-Stark; | 67.5 g |
2-fluro-4-iodoaniline
methanesulfonyl chloride
2-fluoro-4-iodo-1-methanesulfonylaminobenzene
Conditions | Yield |
---|---|
With pyridine at 20℃; for 2h; | 98% |
In pyridine at 20℃; for 2h; | 98% |
With pyridine at 20℃; for 2h; | 95% |
2-fluro-4-iodoaniline
Conditions | Yield |
---|---|
With tert.-butylnitrite; boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether at -10 - 0℃; | 98% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 60℃; for 6h; | 97.6% |
Conditions | Yield |
---|---|
Stage #1: formic acid; 2-fluro-4-iodoaniline With acetic anhydride In tetrahydrofuran; toluene at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; toluene | 97% |
tetrahydrofuran-2-carbonyl chloride
2-fluro-4-iodoaniline
tetrahydro-furan-2-carboxylic acid (2-fluoro-4-iodophenyl)amide
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 18h; | 96% |
With dmap In dichloromethane |
2-fluro-4-iodoaniline
phenylacetylene
2-fluoro-4-phenylethynyl-phenylamine
Conditions | Yield |
---|---|
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; for 18h; Inert atmosphere; | 95% |
2-fluro-4-iodoaniline
tetramethylammonium trifluoromethylselenate(0)
1-amino-2-fluoro-4-[(trifluoromethyl)seleno]benzene
Conditions | Yield |
---|---|
With palladium(l) tri-tert-butylphosphine iodide dimer In toluene at 40℃; for 24h; Glovebox; Inert atmosphere; | 95% |
morpholine-3-one
2-fluro-4-iodoaniline
4-(4-amino-3-fluoro-phenyl)-morpholin-3-one
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 160℃; under 4500.45 - 5250.53 Torr; for 2h; Ullmann-Goldberg Substitution; Microwave irradiation; | 94% |
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux; Inert atmosphere; | 74% |
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux; Inert atmosphere; | 74% |
With potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 140℃; for 2h; microwave; | 33% |
With copper(l) iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 16h; |
2-fluro-4-iodoaniline
3-fluoroisonicotinic acid
3-((2-fluoro-4-iodophenyl)amino)isonicotinic acid
Conditions | Yield |
---|---|
Stage #1: 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at -55℃; Inert atmosphere; Stage #2: 3-fluoroisonicotinic acid In tetrahydrofuran at 20℃; for 96h; Stage #3: With hydrogenchloride In water pH=2; | 94% |
Stage #1: 2-fluro-4-iodoaniline; 3-fluoroisonicotinic acid With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran for 1h; Product distribution / selectivity; | 33% |
Stage #1: 2-fluro-4-iodoaniline With lithium hexamethyldisilazane In tetrahydrofuran at -67 - -59℃; for 2.5h; Inert atmosphere; Stage #2: 3-fluoroisonicotinic acid In tetrahydrofuran for 96h; |
2,3,4-trifluoro-5-vinylbenzoic acid
2-fluro-4-iodoaniline
3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-vinylbenzoic acid
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; | 94% |
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 5.75h; Inert atmosphere; | 94% |
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; | 35% |
pent-2-ynoic acid
2-fluro-4-iodoaniline
4-(4-ethyl-1H-1,2,3-triazol-1-yl)-2-fluoroaniline
Conditions | Yield |
---|---|
With sodium azide; copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; potassium carbonate; L-proline In water; dimethyl sulfoxide at 65℃; | 94% |
2-fluro-4-iodoaniline
diisopropyl-carbodiimide
2-(2-fluoro-4-iodophenyl)-1,3-diisopropylguanidine
Conditions | Yield |
---|---|
at 130℃; for 15h; Inert atmosphere; | 94% |
With dichloro bis(acetonitrile) palladium(II) In toluene at 130℃; under 1500.15 Torr; for 16h; Inert atmosphere; | 72% |
NH-pyrazole
2-fluro-4-iodoaniline
2-fluoro-4-(1H-pyrazol-1-yl)aniline
Conditions | Yield |
---|---|
With copper(l) iodide; 8-quinolinol; potassium carbonate In dimethylsulfoxide-d6 at 120℃; for 16h; Inert atmosphere; | 94% |
With copper(l) iodide; caesium carbonate; trans-1,2-cyclohexanediamine In 1,2-dimethoxyethane at 25 - 86℃; for 72.3333h; Inert atmosphere; | 650 g |
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 1h; | 93% |
tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methyl-phenol In toluene at 100℃; for 1h; | 93% |
(R)-5-chloro-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-8-methylpyrido[2,3-d]pyrimidine-4,7-(3H,8H)-dione
2-fluro-4-iodoaniline
(R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-6-fluoro-5-(2-fluoro-4-iodophenylamino)-8-methylpyrido-[2,3-d]pyrimidine-4,7(3H,8H)-dione
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at -5 - 20℃; Large scale; | 93% |
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; palladium diacetate In 1,4-dioxane at 85℃; for 2h; Product distribution / selectivity; De-gassed solvent; |
2-fluro-4-iodoaniline
1,1'-carbonyldiimidazole
methylamine
N-(2-fluoro-4-iodophenyl)-N'-methylurea
Conditions | Yield |
---|---|
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; Stage #2: methylamine In water; N,N-dimethyl-formamide at 0 - 20℃; | 93% |
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 16h; Inert atmosphere; Stage #2: methylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 1h; | 93% |
Stage #1: 2-fluro-4-iodoaniline; 1,1'-carbonyldiimidazole With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: methylamine In methanol; N,N-dimethyl-formamide at 0 - 20℃; | 92% |
2-fluro-4-iodoaniline
acetic anhydride
N-(2-fluoro-4-iodo-phenyl)-acetamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 25℃; for 2.16667h; | 92% |
In tetrahydrofuran at 0 - 25℃; for 2.16667h; | 92% |
In tetrahydrofuran at 0 - 25℃; for 2.16667h; | 92% |
pyridine-2-thione
2-fluro-4-iodoaniline
Conditions | Yield |
---|---|
With 8-quinolinol; copper(l) iodide In dimethyl sulfoxide at 130℃; | 92% |
3-Methyl-1H-pyridin-2-one
2-fluro-4-iodoaniline
Conditions | Yield |
---|---|
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate In tert-Amyl alcohol at 100℃; for 5h; Inert atmosphere; Glovebox; | 92% |
With 8-quinolinol; copper(l) iodide In dimethyl sulfoxide at 130℃; | 78% |
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