Conditions | Yield |
---|---|
With molecular sieve; nitric acid; acetic anhydride at 0℃; for 3h; other reagent: nitric acid/sulfuric acid; | 98% |
With sulfuric acid; nitric acid at 20℃; for 0.0180556h; Temperature; | 97.3% |
With sulfuric acid; nitric acid at 60 - 70℃; for 6h; | 91% |
4,5-difluoro-2-nitrobenzoic acid
3,4-difluoronitrobenzene
Conditions | Yield |
---|---|
With copper In 1-methyl-pyrrolidin-2-one at 250℃; for 0.5h; | 94% |
3,4-dichloronitrobenzene
A
3,4-difluoronitrobenzene
B
3-chloro-4-fluoronitrobenzene
Conditions | Yield |
---|---|
With potassium fluoride; tetraphenylphosphonium bromide at 175 - 195℃; for 30h; Yields of byproduct given; | A n/a B 79% |
With potassium fluoride; 2-(4-chlorophenyl)propene copolymer-grafted tetraphenylphosphonium chloride; cross-linked styrene In sulfolane at 210℃; for 7h; | A 12% B 64% |
With potassium fluoride; tetraphenylphosphonium bromide at 175 - 195℃; for 30h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With potassium fluoride; 3,4,5,6-tetrafluorophthaloyldifluoride In sulfolane at 200℃; for 13h; | 77% |
Conditions | Yield |
---|---|
With potassium fluoride; benzene-1,2,4,5-tetracarbonyl chloride In sulfolane at 200℃; for 4h; | 58% |
Conditions | Yield |
---|---|
With formic acid; fluorine at 10℃; for 1.75h; Fluorination; | 53% |
1-chloro-2,4-dinitro-benzene
A
3,4-difluoronitrobenzene
B
1,4-difluoro-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium fluoride; tetraphenylphosphonium bromide; Phthaloyl dichloride In sulfolane; toluene at 190℃; for 6h; | A 46% B 3 % Chromat. |
With potassium fluoride; Phthaloyl dichloride; tetraphenylphosphonium bromide In sulfolane 1) 150 deg C, 2 h, 2) 190 deg C, 6 h; | A 46% B 3% |
2,4-Dinitrofluorobenzene
A
3,4-difluoronitrobenzene
B
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With potassium fluoride at 145℃; | |
With potassium fluoride at 155℃; |
1-chloro-2,4-dinitro-benzene
A
3,4-difluoronitrobenzene
B
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With potassium fluoride at 155℃; | |
With potassium fluoride at 145℃; |
1-fluoro-2-fluorosulfonyl-4-nitrobenzene
A
3,4-difluoronitrobenzene
B
2,5-difluorobenzenesulfonyl fluoride
Conditions | Yield |
---|---|
With potassium fluoride; tetraphenylphosphonium bromide In sulfolane; toluene at 210℃; under 300 Torr; Title compound not separated from byproducts; | |
With potassium fluoride; tetraphenylphosphonium bromide In sulfolane at 210℃; under 270 - 300 Torr; for 5h; Yield given. Yields of byproduct given; |
N,N-dimethyl-formamide
1-chloro-2,4-dinitro-benzene
3,4-difluoronitrobenzene
Conditions | Yield |
---|---|
at 150℃; |
3,4-difluoronitrobenzene
Conditions | Yield |
---|---|
at 160℃; under 20 Torr; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 80 percent / phosphoryl chloride / acetonitrile; tetrahydrothiophene 1,1-dioxide; N,N-dimethyl-acetamide / 1 h / 70 °C 2: 90 percent / Ph4PBr, KF / tetrahydrothiophene 1,1-dioxide / 16 h / 130 - 140 °C 3: KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 300 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / 1) 30percent fumic H2SO4 2) NaOH / 16 h / 110 - 115 °C 2: 80 percent / phosphoryl chloride / acetonitrile; tetrahydrothiophene 1,1-dioxide; N,N-dimethyl-acetamide / 1 h / 70 °C 3: 90 percent / Ph4PBr, KF / tetrahydrothiophene 1,1-dioxide / 16 h / 130 - 140 °C 4: KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 300 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / Ph4PBr, KF / tetrahydrothiophene 1,1-dioxide / 16 h / 130 - 140 °C 2: KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 300 Torr View Scheme |
2,4-dichloronitrobenzene
3,4-dichloronitrobenzene
3,4-difluoronitrobenzene
Conditions | Yield |
---|---|
With potassium fluoride In sulfolane |
Conditions | Yield |
---|---|
With potassium fluoride; cesium fluoride In sulfolane | |
With potassium fluoride In sulfolane; dichloromethane | |
With potassium fluoride; bis(triphenylphosphine)iminium chloride In dimethyl sulfoxide at 150℃; for 8h; Inert atmosphere; | 5 %Chromat. |
2,3,4-trifluoronitrobenzene
A
3,4-difluoronitrobenzene
B
1,2-difluoro-3-nitrobenzene
C
2,3,4-trifluoroaniline
Conditions | Yield |
---|---|
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; Overall yield = 95 %Spectr.; regioselective reaction; |
nitrobenzene
A
3-fluoro-1-nitrobenzene
B
3,4-difluoronitrobenzene
C
1,4-difluoro-2-nitrobenzene
D
4-Fluoronitrobenzene
E
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With xenon difluoride; boron trifluoride diethyl etherate at 0 - 25℃; Reagent/catalyst; Cooling with ice; | A 0.16 mmol B 0.001 mmol C 0.016 mmol D 0.01 mmol E 0.05 mmol |
morpholine
3,4-difluoronitrobenzene
3-fluoro-4-(4-morpholinyl)nitrobenzene
Conditions | Yield |
---|---|
Stage #1: morpholine; 3,4-difluoronitrobenzene In tetrahydrofuran at 0 - 20℃; for 1.25h; Stage #2: With citric acid In tetrahydrofuran; water for 1h; | 100% |
In tetrahydrofuran at 0 - 20℃; for 1.25h; | 100% |
In tetrahydrofuran at 20℃; for 1.25h; Cooling with ice-salt bath; | 100% |
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; | 100% |
4-methylpiperidin
3,4-difluoronitrobenzene
3-fluoro-4-(4-methyl-1-piperidinyl)nitrobenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 17h; Heating; | 100% |
In acetonitrile at 80℃; for 16h; |
4,5,6,7-tetrahydrothieno[3,2-c]pyridine
3,4-difluoronitrobenzene
5-(2-fluoro-4-nitrophenyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine
Conditions | Yield |
---|---|
In acetonitrile at 75 - 78℃; for 2h; | 100% |
1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol
3,4-difluoronitrobenzene
4-(2-fluoro-4-nitrophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; | 100% |
With caesium carbonate In ISOPROPYLAMIDE at 100℃; for 1h; | 82% |
With caesium carbonate In ISOPROPYLAMIDE at 100℃; for 1h; | 82% |
3,4-difluoronitrobenzene
methylamine hydrochloride
N-methyl-2-fluoro-4-nitroaniline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; | 100% |
3,4-difluoronitrobenzene
piperidin-3-ol hydrochloride
1-(2-fluoro-4-nitrophenyl)-piperidin-3-ol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50 - 60℃; for 3h; | 100% |
3,4-difluoronitrobenzene
diethyl malonate
1,3-diethyl 2-(2-fluoro-4-nitrophenyl)propanedioate
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide at 70℃; | 100% |
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide; mineral oil at 70℃; | 86% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h; | 80% |
Stage #1: diethyl malonate With sodium hydride In dimethyl sulfoxide at 0 - 20℃; for 2.16667h; Stage #2: 3,4-difluoronitrobenzene In dimethyl sulfoxide at 0 - 20℃; for 2h; | |
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide at 0 - 20℃; | 13 g |
Conditions | Yield |
---|---|
In acetonitrile for 4h; Reflux; | 100% |
In acetonitrile for 4h; Reflux; | 100% |
In acetonitrile for 4h; Reflux; | 73% |
In acetonitrile for 4h; Reflux; |
3,4-difluoronitrobenzene
3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol
5-[4-(2-Fluoro-4-nitrophenoxy)biphenyl-3-yl]-1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 3-(1-methyl-1H-pyrazol-5-yl)biphenyl-4-ol With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide at 20℃; for 16h; | 100% |
3,4-difluoronitrobenzene
4-adamantylphenol
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 20℃; for 4h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 20℃; for 4h; | 703mg |
3,4-difluoronitrobenzene
3-fluoro-4-hydrazinonitrobenzene
Conditions | Yield |
---|---|
With hydrazine In ethanol at 80℃; for 2h; | 99.2% |
With pyridine; hydrazine hydrate at 20℃; for 0.833333h; | 98% |
With potassium carbonate; hydrazine hydrate In acetonitrile | 94% |
Thiomorpholin
3,4-difluoronitrobenzene
(4-(2-fluoro-4-nitrophenyl)thiomorpholine)
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile 1.) RT, 2.) reflux, 24 h; | 99% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 140℃; for 0.25h; Microwave irradiation; | 99% |
Stage #1: Thiomorpholin With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-difluoronitrobenzene In acetonitrile Inert atmosphere; Reflux; | 99% |
piperazine
3,4-difluoronitrobenzene
1-(2-fluoro-4-nitrophenyl)piperazine
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 2h; | 99% |
In acetonitrile at 80℃; for 6h; | 98% |
In acetonitrile at 80℃; for 3h; | 97.7% |
1,2,3,4-tetrahydroisoquinoline
3,4-difluoronitrobenzene
N-(2-fluoro-4-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
In acetonitrile for 5.5h; Heating / reflux; | 99% |
With potassium carbonate In dimethyl sulfoxide for 1h; Substitution; Heating; | 93% |
With triethylamine In ethyl acetate for 3h; Heating / reflux; |
piperidine
3,4-difluoronitrobenzene
1-(2-fluoro-4-nitrophenyl)piperidine
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate at 20℃; | 99% |
With triethylamine In ethyl acetate at 20℃; | 99% |
With triethylamine In ethyl acetate at 20℃; | 99% |
hexamethylene imine
3,4-difluoronitrobenzene
1-(2-fluoro-4-nitrophenyl)azepane
Conditions | Yield |
---|---|
Stage #1: hexamethylene imine With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3,4-difluoronitrobenzene In acetonitrile Inert atmosphere; Reflux; | 99% |
With N-ethyl-N,N-diisopropylamine In acetonitrile for 17h; Heating; | |
With caesium carbonate In DMF (N,N-dimethyl-formamide) | |
With caesium carbonate In N,N-dimethyl-formamide | |
With triethylamine In ethyl acetate at 80℃; for 20h; |
(2R)-2-aminobutan-1-ol
3,4-difluoronitrobenzene
(2R)-(+)-2-(2-fluoro-4-nitrophenyl)amino-1-butanol
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 90℃; for 12h; | 99% |
(2-hydroxyethyl)(methyl)amine
3,4-difluoronitrobenzene
2-[2-Fluoro(methyl)-4-nitroanilino]ethanol
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 100℃; for 1.5h; | 99% |
With N-ethyl-N,N-diisopropylamine In ethyl acetate at 0 - 20℃; for 24h; | 79% |
3-(hydroxymethy)piperidine
3,4-difluoronitrobenzene
[3-fluoro-4-(3-hydroxymethylpiperidino)]nitrobenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 1h; | 99% |
With triethylamine In methanol at 50 - 60℃; for 24h; | 96% |
With triethylamine In methanol at 50 - 60℃; for 24h; | 96% |
3,4-difluoronitrobenzene
phenylmethanethiol
1-(benzylsulfanyl)-2-fluoro-4-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; regioselective reaction; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 15℃; for 3h; |
3,4-difluoronitrobenzene
diethylamine
N,N-diethyl-2-fluoro-4-nitroaniline
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate for 0.5h; | 99% |
With triethylamine In ethyl acetate at 20℃; for 0.5h; Cooling with ice; | 99% |
With triethylamine In ethyl acetate for 0.5h; Cooling with ice; | 99% |
With triethylamine In methanol at 50 - 60℃; for 24h; | 81% |
With triethylamine In methanol at 50 - 60℃; for 24h; | 81% |
3,4-difluoronitrobenzene
2-Methylpiperidin
[3-fluoro-4-(2-methylpiperidino)]nitrobenzene
Conditions | Yield |
---|---|
With triethylamine In methanol at 50 - 60℃; for 28h; | 99% |
With triethylamine In methanol at 50 - 60℃; for 28h; | 99% |
4,4-dimethyl-4-silapiperidine hydrochloride
3,4-difluoronitrobenzene
1-(2-fluoro-4-nitrophenyl)-4,4-dimethyl-1,4-azasilinane
Conditions | Yield |
---|---|
Stage #1: 4,4-dimethyl-4-silapiperidine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide at 0 - 20℃; for 12h; | 99% |
Stage #1: 4,4-dimethyl-4-silapiperidine hydrochloride With triethylamine In ethyl acetate at 25℃; for 0.166667h; Stage #2: 3,4-difluoronitrobenzene In ethyl acetate at 0 - 25℃; for 6h; | 70% |
Stage #1: 4,4-dimethyl-4-silapiperidine hydrochloride With triethylamine In ethyl acetate at 25℃; for 0.166667h; Stage #2: 3,4-difluoronitrobenzene In ethyl acetate at 0 - 25℃; for 6h; | 70% |
With triethylamine In ethyl acetate at 0 - 20℃; for 6h; Inert atmosphere; | 69% |
Stage #1: 4,4-dimethyl-4-silapiperidine hydrochloride With triethylamine In N,N-dimethyl-formamide at 20 - 25℃; for 0.166667h; Stage #2: 3,4-difluoronitrobenzene In N,N-dimethyl-formamide at 20 - 25℃; Cooling with ice; | 28.1 g |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 20℃; for 19h; | 99% |
With potassium carbonate In dimethyl sulfoxide at 20℃; for 19h; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 20℃; for 23h; | 99% |
With potassium carbonate In dimethyl sulfoxide at 20℃; for 23h; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 20℃; for 22h; | 99% |
With potassium carbonate In dimethyl sulfoxide at 20℃; for 22h; | 99% |
4-piperidinemethanol
3,4-difluoronitrobenzene
(1-(2-fluoro-4-nitrophenyl)piperidin-4-yl)methanol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 25℃; for 12h; | 98.8% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; |
3,4-difluoronitrobenzene
6-bromo-1-methyl-1H-indazol-5-ol
6-bromo-5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazole
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 60 - 65℃; for 15h; Large scale; | 98.1% |
With potassium carbonate In tetrahydrofuran at 55℃; for 14h; | 72% |
IUPAC Name: 1,2-difluoro-4-nitrobenzene
Synonyms of 3,4-Difluoronitrobenzene (CAS NO.369-34-6): 1,2-Difluoro-4-nitrobenzene ; Benzene, 1,2-difluoro-4-nitro-
CAS NO: 369-34-6
Molecular Formula: C6H3F2NO2
Molecular Weight: 159.09
Molecular Structure:
EINECS: 206-718-2
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 1
Polar Surface Area: 45.82 Å2
Index of Refraction: 1.509
Molar Refractivity: 32.78 cm3
Molar Volume: 109.6 cm3
Surface Tension: 40.6 dyne/cm
Density: 1.45 g/cm3
Flash Point: 80.6 °C
Enthalpy of Vaporization: 41.84 kJ/mol
Boiling Point: 200 °C at 760 mmHg
Vapour Pressure: 0.469 mmHg at 25°C
Melting Point: -12°C
Water Solubility: insoluble
Appearance: clear yellow liquid
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases
Product Categories: HALIDE;Aromatic Halides (substituted);Fluorine Compounds;Nitro Compounds
3,4-Difluoronitrobenzene (CAS NO.369-34-6) is used as intermediates in medicine, pesticide.
Safety Information about 3,4-Difluoronitrobenzene (CAS NO.369-34-6)
Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-20/21/22
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 2810
WGK Germany: 3
RTECS: CZ5710000
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Combustible liquid.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container.
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