Conditions | Yield |
---|---|
With water; sodium hydroxide at 80 - 155℃; for 35h; Sealed tube; | 94.1% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 0.416667h; | A 6% B 94% |
Conditions | Yield |
---|---|
With acetic acid; Selectfluor; eosin y In water at 20℃; for 6h; Irradiation; Green chemistry; | 70% |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
para-difluorobenzene
A
1,2,4-trifluorobenzene
B
2,5-difluorophenol
C
4H/5H-3,3,4,5,6,6-Hexafluor-cyclohexen
D
3,3,6,6-tetrafluoro-1,4-cyclohexadiene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; fluorine In trichlorofluoromethane at -25℃; for 3h; Further byproducts given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With hydrogenchloride; n-butyllithium; dihydrogen peroxide In tetrahydrofuran; hexane; toluene | |
With hydrogenchloride; n-butyllithium; dihydrogen peroxide In tetrahydrofuran; hexane; toluene |
para-difluorobenzene
A
4-Fluorophenol
B
2,4-difluorophenol
C
2,5-difluorophenol
D
hydrogen fluoride
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 15h; Catalytic behavior; |
2,5-difluorophenol
N,N-diethylcarbamyl chloride
O-2,5-difluorophenyl N,N-diethylcarbamate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 70℃; for 13.5h; | 100% |
Stage #1: 2,5-difluorophenol With sodium hydroxide In tetrahydrofuran for 0.166667h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 24h; | 92% |
Stage #1: 2,5-difluorophenol With sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 24h; | |
Stage #1: 2,5-difluorophenol With sodium hydroxide In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; |
Conditions | Yield |
---|---|
at 170℃; for 1h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2,5-difluorophenol; propargyl bromide With sodium carbonate In acetone at 60℃; for 8.5h; Stage #2: In acetone at 25℃; for 15h; | 99% |
With potassium carbonate In acetone for 24h; Inert atmosphere; Reflux; | 96.7% |
With caesium carbonate In acetonitrile | 92% |
With potassium carbonate In acetone at 60℃; for 24h; Inert atmosphere; | 88% |
2,5-difluorophenol
tert-butyldimethylsilyl chloride
1-tert-butyldimethylsilyloxy-2,5-difluorobenzene
Conditions | Yield |
---|---|
Stage #1: 2,5-difluorophenol With sodium hydride In N,N-dimethyl-formamide for 0.5h; cooling; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide for 1h; | 94% |
Stage #1: 2,5-difluorophenol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 15h; | 80% |
In N,N-dimethyl-formamide; mineral oil | 26.65 g (94%) |
Conditions | Yield |
---|---|
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: 2,5-difluorophenol With sodium hydroxide In water Stage #3: With hydrogenchloride more than 3 stages; | 93% |
Stage #1: aniline With hydrogenchloride; sodium nitrite In water Stage #2: 2,5-difluorophenol With sodium hydroxide; urea In water at 0 - 20℃; | 74% |
N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester
2,5-difluorophenol
tert-butyl [5-(2,5-difluorophenoxy)-2-nitrophenyl]methylcarbamate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With sodium metaborate tetrahydrate In water at 40℃; for 12h; Green chemistry; regioselective reaction; | 92% |
2,5-difluorophenol
3,4-bis(4-methoxyphenyl)-6-chloropyridazine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 24h; | 91.5% |
at 150℃; for 24h; | 91.5% |
2,5-difluorophenol
chloromethyl methyl ether
1,4-difluoro-2-(methoxymethoxy)benzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 2h; | 91% |
Stage #1: 2,5-difluorophenol With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In dichloromethane at 20℃; for 16h; | 77.97% |
2,5-difluorophenol
(S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: 2,5-difluorophenol; (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 20℃; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 2h; Heating; | 89% |
With potassium carbonate In acetone for 2h; Reflux; | 81.4% |
2,5-difluorophenol
1-(2-methoxyphenyl)-1H-pyrazol
1-(2',5'-difluoro-3-methoxybiphenyl-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With [Ru(MesCO2)2(p-cymene)]; potassium carbonate; p-toluenesulfonyl chloride In toluene at 120℃; for 18h; Inert atmosphere; chemoselective reaction; | 89% |
2,5-difluorophenol
(hex-1-en-3-yl)methyl carbonate
Conditions | Yield |
---|---|
With (R,R)-(−)-2,3-bis(t-butylmethylphosphino)quinoxaline; chloro(1,5-cyclooctadiene)rhodium(I) dimer In dichloromethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; enantioselective reaction; | 88% |
2,5-difluorophenol
2-bromo-3,6-difluoro phenol
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrahydrofuran at -40℃; for 2h; | 85.3% |
With N-Bromosuccinimide In tetrahydrofuran at -40 - 20℃; for 1h; | 57% |
With N-Bromosuccinimide; isopropylamine In tetrahydrofuran at -40 - 20℃; for 0.5h; | 51% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 84% |
trifluoromethylsulfonic anhydride
2,5-difluorophenol
Trifluoro-methanesulfonic acid 2,5-difluoro-phenyl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 4h; Ambient temperature; | 84% |
Conditions | Yield |
---|---|
With phosphoric acid In toluene at 90℃; for 20h; | 82% |
2,5-difluorophenol
4-bromo-2,5-difluoro phenol
Conditions | Yield |
---|---|
With bromine In chloroform at 0 - 20℃; for 3h; | 81.05% |
With bromine In chloroform for 3h; | 70.2% |
With bromine In chloroform for 3h; | 70.2% |
With bromine; trifluoroacetic acid at 20℃; |
2,5-difluorophenol
4-Fluoronitrobenzene
1,4-difluoro-2-(4-nitrophenoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2.33333h; Inert atmosphere; Stage #2: 2,5-difluorophenol With copper(l) chloride In N,N-dimethyl-formamide; mineral oil at 100℃; for 12h; | 81% |
Stage #1: 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2.33333h; Inert atmosphere; Stage #2: 2,5-difluorophenol; copper(l) chloride In N,N-dimethyl-formamide; mineral oil at 25 - 100℃; for 12.1667h; | 81% |
Stage #1: 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 2.33333h; Stage #2: 2,5-difluorophenol With copper(l) chloride In N,N-dimethyl-formamide at 25 - 100℃; for 12h; | 81% |
Stage #1: 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 2.33h; Stage #2: 2,5-difluorophenol With copper(l) chloride In N,N-dimethyl-formamide at 25 - 100℃; for 12.13h; | 81% |
Stage #1: 4-Fluoronitrobenzene With sodium hydride In N,N-dimethyl-formamide at 0 - 25℃; for 2.33333h; Stage #2: 2,5-difluorophenol With copper(l) chloride In dichloromethane at 25 - 100℃; for 12h; | 81% |
2,5-difluorophenol
propargyl bromide
2,4-difluoro-1-(prop-2-yn-1-yloxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating / reflux; | 80% |
Conditions | Yield |
---|---|
With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In tetrahydrofuran at 50℃; for 24h; Inert atmosphere; | 79% |
With (bis(tricyclohexyl)phosphine)palladium(II) dichloride In tetrahydrofuran at 50℃; for 24h; | 79% |
4-[4-(3-hydroxypropyl)phenyl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
2,5-difluorophenol
4-{4-[3-(2,5-difluorophenoxy)propyl]phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester
Conditions | Yield |
---|---|
With tributylphosphine; N-ethyl-N,N-diisopropylamine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20 - 60℃; for 3h; | 77% |
6-(4-hydroxypiperidin-1-yl)-N-isopentylpyridazine-3-carboxamide
2,5-difluorophenol
Conditions | Yield |
---|---|
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 25℃; for 0.5h; Mitsunobu reaction; | 70% |
2,5-difluorophenol
Conditions | Yield |
---|---|
With bromine; iron In various solvent(s) Heating; | 66.3% |
Ethyl 2-butynoate
2,5-difluorophenol
3-(2,5-difluoro-phenoxy)-but-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 130℃; for 2h; | 63% |
2,5-difluorophenol
cis-3-hydroxycyclobutylcarboxylic acid methyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 72h; | 63% |
4-chloro-3-iodopyridin-2-ylamine
2,5-difluorophenol
4-(2,5-difluorophenoxy)-3-iodopyridin-2-amine
Conditions | Yield |
---|---|
Stage #1: 4-chloro-3-iodopyridin-2-ylamine; 2,5-difluorophenol With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 170℃; for 6h; Microwave irradiation; Stage #2: With sodium hydroxide In 1-methyl-pyrrolidin-2-one; water | 62.1% |
Hazard Code:Xn,Xi,C,F
Risk Statements:10-20/21/22-36/37/38-34-11
10:Flammable
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
34:Causes burns
11:Highly Flammable
Safety Statements:16-26-36/37-45-36/37/39-36
16:Keep away from sources of ignition - No smoking
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
36:Wear suitable protective clothing
RIDADR:UN 1325 4.1/PG 2
WGK Germany:3
Hazard Note:Irritant
HazardClass:4.1
PackingGroup:II
Chemical Stability:Stable under normal temperatures and pressures.
Conditions to Avoid:Incompatible materials, ignition sources.
Incompatibilities with Other Materials:Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:Carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization:Will not occur.
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