2,6-difluorobenzamide
2,6-difluoroaniline
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hydroxide In water at -5℃; for 2h; Reagent/catalyst; Hofmann Rearrangement; Large scale; Green chemistry; | 92% |
With sodium hypochlorite; sodium hydroxide at -5℃; for 1.5h; Large scale; | 89.6% |
1-chloro-2,6-difluorobenzene
A
ortho-difluorobenzene
B
2,6-difluoroaniline
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(I) oxide at 160℃; for 24h; bomb; Further byproducts given; | A 2% B 71% |
Conditions | Yield |
---|---|
With naphtophenone at 25℃; for 4h; Product distribution; Irradiation; further tenmperatures; | A 54% B 13% C 10% |
Conditions | Yield |
---|---|
With sodium azide; sulfuric acid |
1-chloro-3,5-difluorobenzene
A
2,4-difluorophenylamine
B
2,6-difluoroaniline
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With ammonium hydroxide; cesium fluoride; copper(I) oxide 1.) N,N'-dimethylethyleneurea, 250 deg C (bomb), 12 h, 2.) 170 deg C (bomb), 24 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; | |
With ammonium hydroxide; cesium fluoride; copper(I) oxide 1.) N,N'-dimethylethyleneurea, 250 deg C (bomb), 12 h, 2.) 160 deg C (bomb), 24 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) CsF, 2.) H2, N-ethyldiethanolamine / 2.) 10percent Pd/C / 1.) N,N'-dimethylethyleneurea, 250 deg C (bomb), 12 h, 2.) ethylene glycol, 100 deg C, 200 psi 2: 71 percent / conc. NH4OH / Cu2O / 24 h / 160 °C / bomb View Scheme | |
Multi-step reaction with 2 steps 1: CsF / various solvent(s) / 12 h / 250 °C / reaction carried out in a bomb 2: 71 percent / conc. NH4OH / Cu2O / 24 h / 160 °C / bomb View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: KF / various solvent(s) / 12 h / 300 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) nBuLi, (ii) /BRN= 1900390/ 2: NaN3, H2SO4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C 2.1: potassium nitrate; bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethyl acetate / 12 h / 90 °C / Sealed tube 2.2: 0.17 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C 2.1: potassium nitrate; bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethanol / 12 h / 55 °C / Sealed tube 2.2: 0.17 h / 20 °C 3.1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C 4.1: potassium nitrate; bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethyl acetate / 12 h / 90 °C / Sealed tube 4.2: 0.17 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 2,2'-difluoroazobenzene With N-fluorobis(benzenesulfon)imide; potassium nitrate; bis(dibenzylideneacetone)-palladium(0) In ethyl acetate at 90℃; for 12h; Sealed tube; Stage #2: With sodium tetrahydroborate; copper(l) chloride In ethanol at 20℃; for 0.166667h; | 41.3 mg |
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 2: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
Azobenzene
2,6-difluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium nitrate; bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethanol / 12 h / 55 °C / Sealed tube 1.2: 0.17 h / 20 °C 2.1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C 3.1: potassium nitrate; bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide / ethyl acetate / 12 h / 90 °C / Sealed tube 3.2: 0.17 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 55 °C 2: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 3: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
2,6-difluoroaniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; copper(l) chloride In ethanol at 20℃; | 23.2 mg |
2,6-difluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethyl acetate / 2 h / 20 °C / Sealed tube 2: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 55 °C 3: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 4: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: N-fluorobis(benzenesulfon)imide / ethyl acetate / 2 h / 20 °C / Sealed tube 2: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 55 °C 3: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 4: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1: dichloromethane / 24 h / 20 °C 2: ethyl acetate / 2 h / 20 °C / Sealed tube 3: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 55 °C 4: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 5: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
2,6-difluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethyl acetate / 2 h / 20 °C / Sealed tube 2: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 55 °C 3: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 105 °C / Sealed tube 4: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
1-(2,4,6-trimethylphenyl)-2-phenyldiazene
2,6-difluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 100 °C / Sealed tube 2: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
2,6-difluoroaniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; copper(l) chloride In ethanol at 20℃; | 24.8 mg |
2,6-difluoroaniline
1,3-difluoro-2-nitrosobenzene
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 23℃; Inert atmosphere; | 100% |
With Oxone In dichloromethane; water at 20℃; for 15h; | 99% |
With potassium peroxymonosulfate sulfate In dichloromethane; water at 20℃; for 24h; | 86.49% |
2,6-difluoroaniline
2,6-difluoro-4-iodoaniline
Conditions | Yield |
---|---|
With N-iodo-succinimide; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 5 - 20℃; for 2.5h; | 100% |
With Iodine monochloride In acetic acid at 20℃; for 0.25h; | 95% |
Stage #1: 2,6-difluoroaniline With Iodine monochloride; acetic acid In water at 20℃; for 0.25h; Stage #2: With sodium carbonate In water | 95% |
2,6-difluoroaniline
Ethyl oxalyl chloride
ethyl 2-((2,6-difluorophenyl)amino)-2-oxoacetate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 24h; | 100% |
With triethylamine In tetrahydrofuran at 0℃; for 16h; Inert atmosphere; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; | 99% |
With hydrogenchloride In dichloromethane for 3h; Ambient temperature; | 78% |
In hydrogenchloride; dichloromethane |
2,6-difluoroaniline
4-bromo-2,6-difluoroaniline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 20℃; | 99% |
With N-Bromosuccinimide In chloroform at 20℃; | 93% |
Stage #1: 2,6-difluoroaniline With bromine; acetic acid In water at 20℃; for 0.25h; Stage #2: With sodium carbonate In water | 92% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 16h; | 98% |
In toluene at 0 - 20℃; for 4h; Solvent; Temperature; | 94% |
91% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In toluene at 120℃; for 16h; | 98% |
2,6-difluoroaniline
potassium ethyl xanthogenate
2-mercapto-4-fluorobenzothiazole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 0.133333h; microwave irradiation; | 98% |
In N,N-dimethyl-formamide at 120℃; for 3.5h; Inert atmosphere; | 98% |
In N,N-dimethyl-formamide at 120℃; for 3.5h; Inert atmosphere; | 98% |
In 1-methyl-pyrrolidin-2-one at 90℃; for 2h; | 56% |
In N,N-dimethyl-formamide at 120℃; for 4h; |
methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate
2,6-difluoroaniline
N-(2,6-difluorophenyl)-3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide
Conditions | Yield |
---|---|
Stage #1: methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}-2-methylphenyl)amino}-4-pyrimidinyl]imidazo[1,2-a]pyridin-2-yl)benzoate; 2,6-difluoroaniline With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water | 98% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; Buchwald-Hartwig Coupling; Inert atmosphere; | 98% |
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere; | 96% |
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine In toluene at 100℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In methanol; water at 20℃; | 98% |
Stage #1: 2,6-difluoroaniline With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃; for 0.75h; Stage #2: acetylacetone With sodium acetate In ethanol; water for 1h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: acetylacetone With sodium acetate In ethanol; water at 0 - 20℃; for 10h; | 98% |
2,6-difluoroaniline
2-nitrobenzyl chloride
N-(2,6-difluorophenyl)-2-nitrobenzamide
Conditions | Yield |
---|---|
In 1,4-dioxane at 20℃; | 97% |
Conditions | Yield |
---|---|
In [D3]acetonitrile at 20℃; for 6h; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
Stage #1: acetaldehyde With sodium tetrahydroborate; acetic acid In 1,2-dichloro-ethane at 0 - 20℃; for 1h; Stage #2: 2,6-difluoroaniline In 1,2-dichloro-ethane at 20℃; | 97% |
Conditions | Yield |
---|---|
Stage #1: 2-bromothiazole-4-carboxylic Acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2,6-difluoroaniline In N,N-dimethyl-formamide at 20℃; for 16h; | 96% |
2,6-difluoroaniline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 96% |
With triethylamine In dichloromethane at 20℃; for 1h; | 96% |
2,6-difluoroaniline
2-(4-bromophenyl)benzothiazole
Conditions | Yield |
---|---|
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; Sealed tube; | 96% |
2,6-difluoroaniline
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
at 150℃; for 16h; Schlenk technique; Inert atmosphere; | 95.3% |
2,6-difluoroaniline
pivaloyl chloride
N-(2,6-difluorophenyl)trimethylacetamide
Conditions | Yield |
---|---|
With triethylamine In toluene at 0 - 50℃; | 95% |
In toluene at 20℃; Reflux; |
2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine
2,6-difluoroaniline
florasulam
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline With N-chloro-succinimide; dimethylsulfide In acetonitrile at -20℃; Inert atmosphere; Stage #2: 2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine With 3-Methylpyridine In acetonitrile at 20 - 40℃; Temperature; Inert atmosphere; | 94.2% |
In propylene glycol at 40℃; for 1.5h; Product distribution / selectivity; | 88% |
In propylene glycol; dichloromethane at 25 - 45℃; for 5.5 - 8h; Product distribution / selectivity; | 84.6% |
2,6-difluoroaniline
N-sulfinyl-2,6-diflouroaniline
Conditions | Yield |
---|---|
With N-(chlorosulfinyl)imidazole In dichloromethane at -40 - 20℃; for 1.5h; Inert atmosphere; | 94% |
With thionyl chloride |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In tetrahydrofuran at 100℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry; | 94% |
2,6-difluoroaniline
4-acetophenyl triflate
Conditions | Yield |
---|---|
With C46H27F24FeNiP2(1+)*CF3O3S(1-); triethylamine In 2-methyltetrahydrofuran at 100℃; for 16h; Concentration; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With acetic acid; isopentyl nitrite at 0 - 5℃; Diazotization; | 93% |
2,6-difluoroaniline
ortho-nitrofluorobenzene
2,6-difluoro-N-(2-nitrophenyl)aniline
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline With sodium tert-amylate In tetrahydrofuran at 0 - 10℃; for 1.11667h; Large scale reaction; Stage #2: ortho-nitrofluorobenzene In tetrahydrofuran at 9 - 15℃; for 3h; Thermodynamic data; Concentration; Time; Large scale reaction; | 93% |
Stage #1: 2,6-difluoroaniline With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.166667h; Stage #2: ortho-nitrofluorobenzene In tetrahydrofuran; pentane at 0 - 20℃; for 0.5h; | 68% |
Stage #1: 2,6-difluoroaniline With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: ortho-nitrofluorobenzene In N,N-dimethyl-formamide for 16h; |
2-chloro-7-(1-methyl-1H-pyrazol-4-yl)-1,5-naphthyridine
2,6-difluoroaniline
C18H13F2N5
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Stage #2: 2-chloro-7-(1-methyl-1H-pyrazol-4-yl)-1,5-naphthyridine In tetrahydrofuran at 0 - 20℃; | 93% |
1,3-diphenyl-3-hydroxypropene
2,6-difluoroaniline
Conditions | Yield |
---|---|
With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 3h; regioselective reaction; | 93% |
2,6-difluoroaniline
4-bromo-2,6-difluoroaniline
Conditions | Yield |
---|---|
Stage #1: 2,6-difluoroaniline; 4-bromo-2,6-difluoroaniline With Oxone In dichloromethane; water at 20℃; for 17h; Inert atmosphere; Stage #2: In acetic acid; toluene; trifluoroacetic acid at 20℃; | 93% |
Conditions | Yield |
---|---|
In toluene at 0 - 20℃; for 4h; | 93% |
This chemical has the systematic name 2,6-Difluoroaniline. With the CAS registry number 5509-65-9, it is also known as Benzenamine, 2,6-difluoro-. Its molecular formula is C6H5F2N and its molecular weight is 129.11. Additionally, it's ued in the manufacture of pesticides, fungicides and herbicides. It is also an important intermediate of medicines and pesticides. However, it should be sealed at the cool and dry place.
Other characteristics of the 2,6-Difluoroaniline can be summarised as followings: (1)ACD/LogP: 1.65; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.65; (4)ACD/LogD (pH 7.4): 1.65; (5)ACD/BCF (pH 5.5): 10.51; (6)ACD/BCF (pH 7.4): 10.51; (7)ACD/KOC (pH 5.5): 187.46; (8)ACD/KOC (pH 7.4): 187.5; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 3.24 Å2; (13)Index of Refraction: 1.52; (14)Molar Refractivity: 30.47 cm3; (15)Molar Volume: 100.1 cm3; (16)Polarizability: 12.08×10-24cm3; (17)Surface Tension: 37.2 dyne/cm; (18)Density: 1.289 g/cm3; (19)Flash Point: 43.3 °C; (20)Enthalpy of Vaporization: 39.08 kJ/mol; (21)Boiling Point: 154 °C at 760 mmHg; (22)Vapour Pressure: 3.25 mmHg at 25°C.
Production method of the 2,6-Difluoroaniline: It could be obtained by the reactant of 2-chloro-1,3-difluorobenzene. This reaction needs the reagent of conc. NH4OH, and the catalyst of Cu2O. The yield is 71 %. In addition, this reaction should be taken for 24 hours at the temperature of 160 °C. The other condition is bomb.
Uses of the 2,6-Difluoroaniline: It could be used to produce the 2,6,2',6'-Tetrafluorazoxybenzol. This reaction needs the reagents of aq. H2O2, H2SO4.
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. As it's flammable, keep it away from the sources of ignition.
You can still convert the following datas into molecular structure:
1.SMILES: Fc1cccc(F)c1N
2.InChI: InChI=1/C6H5F2N/c7-4-2-1-3-5(8)6(4)9/h1-3H,9H2
3.InChIKey: ODUZJBKKYBQIBX-UHFFFAOYAU
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