Conditions | Yield |
---|---|
With Cu(Ph3P)3F In N,N-dimethyl-formamide at 170℃; for 5h; | 100% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 1.5h; Ambient temperature; | 100% |
With tetrabutyl ammonium fluoride In tetrahydrofuran; water; N,N-dimethyl-formamide at 20℃; for 1h; | 72% |
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature; Yield given; | |
With tetraphenylphosphonium hydrogendifluoride In sulfolane at 100℃; for 2h; | 70 % Chromat. |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere; chemoselective reaction; | 97.4 %Chromat. |
Conditions | Yield |
---|---|
With nitric acid In 1,2-dichloro-ethane at 70℃; for 16h; Inert atmosphere; | 96% |
With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction; | 80% |
With N–nitrosuccinimide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 20℃; for 19h; Inert atmosphere; Irradiation; | 68% |
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C / Sealed tube 1.2: 0.25 h / 20 °C / Sealed tube 2.1: sodium triflate; sodium nitrite / ethyl acetate / 16 h / 70 °C / Sealed tube View Scheme |
Conditions | Yield |
---|---|
With sulfolane; sodium hydrogencarbonate at 190℃; for 2h; | 92% |
cetyltributylphosphonium bromide
2-Chloronitrobenzene
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With potassium fluoride | 91.2% |
Conditions | Yield |
---|---|
With potassium fluoride; polydiallyldimethylammonium chloride In dimethyl sulfoxide at 200℃; for 3h; | 90.1% |
With potassium fluoride; bis(tricyclohexylphosphine)nickel(II) dichloride; tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 150℃; for 8h; Inert atmosphere; | 79.8% |
With potassium fluoride; bis(triphenylphosphine)iminium chloride In dimethyl sulfoxide at 150℃; for 8h; Inert atmosphere; | 76% |
Conditions | Yield |
---|---|
With potassium fluoride | 84.6% |
Conditions | Yield |
---|---|
With nitric acid at 50℃; for 3h; | A 84.4% B 13.9% |
With 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide at 55 - 60℃; for 3h; Inert atmosphere; Sealed tube; Overall yield = 96 percent; | A 76.8% B 19.2% |
With aluminium trichloride; dinitrogen tetraoxide; Petroleum ether |
bis(2-fluorophenyl)iodonium tetrafluoroborate
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With sodium triflate; sodium nitrite In ethyl acetate at 70℃; for 16h; Sealed tube; | 84% |
Conditions | Yield |
---|---|
Stage #1: o-nitroiodobenzene With phenyllithium In tetrahydrofuran; diethyl ether; cyclohexane at -28℃; Flow reactor; Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran; diethyl ether; cyclohexane at -28℃; Flow reactor; | 83% |
cetyltrimethylammonium bromide
2-Chloronitrobenzene
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With potassium fluoride In water; toluene | 78% |
Conditions | Yield |
---|---|
70% |
nitrobenzene
A
3-fluoro-1-nitrobenzene
B
2,6-difluoro-1-nitrobenzene
C
4-Fluoronitrobenzene
D
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With tetrafluoroammonium tetrafluoroborate In hydrogen fluoride at 0℃; Further byproducts given. Title compound not separated from byproducts; | A 62% B n/a C 6% D 15% |
With tetrafluoroammonium tetrafluoroborate In hydrogen fluoride at 0℃; Yield given. Further byproducts given. Title compound not separated from byproducts; | A 62% B n/a C 6% D 15% |
With tetrafluoroammonium tetrafluoroborate In hydrogen fluoride at 0℃; Further byproducts given. Title compound not separated from byproducts; | A 62 % Spectr. B n/a C 6 % Spectr. D 15 % Spectr. |
dimethyl-(2-nitro-phenyl)-sulfonium ; methyl sulfate
A
methyl 2-nitrophenyl sulfide
B
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide at 100℃; for 0.166667h; | A 25% B 56% |
Conditions | Yield |
---|---|
Stage #1: o-nitroiodobenzene With phenyllithium In tetrahydrofuran; diethyl ether; cyclohexane at -28℃; Flow reactor; Stage #2: With 2-fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide In tetrahydrofuran; diethyl ether; cyclohexane at -28℃; Flow reactor; | A 24% B 56% |
Conditions | Yield |
---|---|
Stage #1: ortho-nitrobenzoic acid With tetrakis(acetonitrile)copper(I)tetrafluoroborate; tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 23℃; for 0.5h; Sealed tube; Inert atmosphere; Stage #2: In acetonitrile at 35℃; Irradiation; Sealed tube; Inert atmosphere; | 54% |
2-Fluoroaniline
trifluoroacetic acid
B
ortho-nitrofluorobenzene
C
2,2'-difluoroazobenzene
Conditions | Yield |
---|---|
With Oxone In dimethyl sulfoxide at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction; | A 25% B 15% C 40% |
2-Fluoroaniline
trifluoroacetic acid
A
2,2,2-trifluoro-N-(2-hydroxyphenyl)acetamide
C
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With Oxone In acetonitrile at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction; | A 10% B 25% C 8% |
2-Fluoroaniline
trifluoroacetic acid
A
ortho-nitrofluorobenzene
B
2,2'-difluoroazobenzene
Conditions | Yield |
---|---|
With Oxone In N,N-dimethyl-formamide at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction; | A 10% B 20% |
4-cyanophenol
1,2-Dinitrobenzene
A
4-(2-nitrophenoxy)benzonitrile
B
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide at 110℃; for 2h; | A n/a B 10% |
With potassium fluoride In dimethyl sulfoxide at 110℃; for 2h; | A n/a B 10 % Chromat. |
Conditions | Yield |
---|---|
With Oxone In dichloromethane at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction; | 10% |
fluorobenzene
nitro acetate
A
4-Fluoronitrobenzene
B
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With nitric acid; phosphorus pentoxide beim Nitrieren; Trennung vom p-Isomeren durch fraktionierte Destillation und Krystallisation; |
Conditions | Yield |
---|---|
Diazotization.nachfolgend Reduktion zu 4-Fluor-3-nitro-phenylhydrazin und Oxydation mit Kupfersulfat; |
fluorobenzene
methyl nitrate
A
3-fluoro-1-nitrobenzene
B
4-Fluoronitrobenzene
C
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
Product distribution; gas-phase radiolytic nitration; |
fluorobenzene
A
3-fluoro-1-nitrobenzene
B
4-Fluoronitrobenzene
C
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
With silver nitrate; boron trifluoride In acetonitrile at 25℃; for 10h; Product distribution; competitive nitration benzene, relative rate; | A 1 % Chromat. B 72 % Chromat. C 27 % Chromat. |
With methyl nitrate; methane at 37.6℃; Product distribution; Irradiation; gas-phase nitration by radiolytically formed MeO(1+)(H)NO2; | |
With nitro acetate; H-ZSM-11 In hexane at 30℃; Product distribution; different catalysts; |
Conditions | Yield |
---|---|
With K10 montmorillonite-supported cupric nitrate; acetic anhydride In hexane for 48h; Product distribution; Ambient temperature; var. halobenzenes, other solvent, other time; |
4-cyanophenyl methyl ketone
1-fluoro-2-nitro-benzene radical anion
B
ortho-nitrofluorobenzene
Conditions | Yield |
---|---|
at 149.9℃; Thermodynamic data; ΔG0; |
Conditions | Yield |
---|---|
In toluene at 25℃; Rate constant; also in DMSO; | 100% |
In toluene at 25℃; | 100% |
97% |
Conditions | Yield |
---|---|
In ethanol; water Reflux; | 100% |
In methanol; water Heating; | 98% |
In water at 20℃; for 2h; Inert atmosphere; | 93% |
N,N-dimethylethylenediamine
ortho-nitrofluorobenzene
N1,N1-dimethyl-N2-(2-nitrophenyl)ethane-1,2-diamine
Conditions | Yield |
---|---|
In toluene at 25℃; Rate constant; also in DMSO; | 100% |
In toluene at 25℃; | 100% |
In isopropyl alcohol at 90 - 100℃; for 16h; | 92% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 50℃; under 5400430 Torr; for 20h; | 100% |
With potassium carbonate In acetonitrile for 3h; Heating / reflux; | 100% |
With potassium carbonate In acetonitrile at 90℃; for 3h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In toluene at 25℃; | 100% |
In toluene at 25℃; Rate constant; Mechanism; also in DMSO; | 100% |
With potassium phosphate; TPGS-750-M In water at 20℃; for 18h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With 1,2,3-Benzotriazole; potassium tert-butylate; copper(l) iodide In dimethyl sulfoxide at 110℃; for 0.5h; | 100% |
With pyridine; potassium carbonate; copper(II) oxide at 115℃; Ullmann Condensation; | 96% |
With potassium carbonate In acetonitrile for 24h; Heating; | 95% |
1,2,3,4-tetrahydroisoquinoline
ortho-nitrofluorobenzene
1,2,3,4-tetrahydro-2-(2-nitrophenyl)isoquinoline
Conditions | Yield |
---|---|
In neat (no solvent) at 100℃; for 1h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 100℃; | 81% |
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; Reflux; | 60% |
2-hydroxybromobenzene
ortho-nitrofluorobenzene
1-(2-bromophenoxy)-2-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 95℃; for 23h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 95℃; | 95% |
With caesium carbonate In N,N-dimethyl-formamide at 0 - 80℃; for 3h; | 90% |
ethyl 2-cyanoacetate
ortho-nitrofluorobenzene
(+/-)-ethyl cyano(2-nitrophenyl)acetate
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide 1.) 10 min, 2.) 90 deg C, 0.5 h; | 100% |
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In dimethyl sulfoxide at 20 - 90℃; Inert atmosphere; | 99% |
Stage #1: ethyl 2-cyanoacetate With potassium tert-butylate In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: ortho-nitrofluorobenzene In tetrahydrofuran for 3h; Reflux; | 96.4% |
6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
ortho-nitrofluorobenzene
6,7-dimethoxy-(N-2-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline
Conditions | Yield |
---|---|
In neat (no solvent) at 100℃; for 1h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 100℃; for 4h; | 40% |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; | |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; |
methyl 2-(2-acetyl-4,5-dimethoxyphenyl)acetate
ortho-nitrofluorobenzene
methyl 2-[2-(2-nitrophenyl)acetyl]-4,5-dimethoxyphenylacetate
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane for 2h; Heating; | 100% |
ortho-cresol
ortho-nitrofluorobenzene
1-methyl-2-(2-nitrophenoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 95℃; for 20h; | 100% |
Stage #1: ortho-cresol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: ortho-nitrofluorobenzene In N,N-dimethyl-formamide at 20 - 50℃; for 13h; Inert atmosphere; | 93% |
Stage #1: ortho-cresol With potassium tert-butylate In tetrahydrofuran for 1h; Stage #2: ortho-nitrofluorobenzene In tetrahydrofuran |
4-tert-Butylaniline
ortho-nitrofluorobenzene
(4-tert-butyl-phenyl)-(2-nitro-phenyl)-amine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 100℃; | 100% |
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 65℃; for 18h; | 54% |
With triethylamine In N,N-dimethyl-formamide at 80℃; for 12h; |
2-(3,4-dimethoxyphenyl)-ethylamine
ortho-nitrofluorobenzene
N-[2-(3,4-dimethoxyphenyl)ethyl]-2-nitroaniline
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 70℃; for 16h; | 100% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0966667h; microwave irradiation; | |
With diisopropylamine In N,N-dimethyl-formamide microwave irradiation; | |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Microwave irradiation; |
ortho-nitrofluorobenzene
4-bromo-aniline
4-bromo-N-(2-nitrophenyl)benzenamine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 100℃; for 48h; Inert atmosphere; Schlenk technique; | 100% |
With potassium fluoride at 170 - 180℃; for 30h; | 92% |
With potassium fluoride at 150℃; for 18h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol; water for 5h; Heating; | 100% |
With sodium hydrogencarbonate In ethanol; water Heating; | 94% |
With triethylamine In dimethyl sulfoxide | 80.3% |
With sodium hydrogencarbonate In ethanol; water at 100℃; |
phenyltrimethylsilyl ether
ortho-nitrofluorobenzene
1-nitro-2-phenoxy-benzene
Conditions | Yield |
---|---|
t-Bu-P4 base In hexane; N,N-dimethyl-formamide at 20℃; for 6h; | 100% |
3-amino-2,2-dimethylpropan-1-ol
ortho-nitrofluorobenzene
2,2-dimethyl-3-(2-nitrophenylamino)propan-1-ol
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With triethylsilane; t-Bu-P4 In hexane; dimethyl sulfoxide at 100℃; for 2h; | 100% |
ortho-nitrofluorobenzene
(R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: (R)-3-aminopyrrolidine-1-carboxylic acid tert-butyl ester With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: ortho-nitrofluorobenzene In N,N-dimethyl-formamide at 80℃; for 16h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; |
3-(1-pyrrolidinyl)propylamine
ortho-nitrofluorobenzene
2-Nitro-1-(3-pyrrolidino-propylamino)-benzol
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; | 100% |
In tetrahydrofuran at 30℃; for 12h; Inert atmosphere; |
N,N',N'-trimethylenediamine
ortho-nitrofluorobenzene
N,N,N'-trimethyl-N'-(2-nitrophenyl)-1,2-ethanediamine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In ethanol at 80℃; for 16h; | 100% |
ortho-nitrofluorobenzene
1,1-dimethylethyl (3R)-3-(aminomethyl)-1-piperidinecarboxylate
1,1-dimethylethyl (3R)-3-{[(2-nitrophenyl)amino]methyl}-1-piperidinecarboxylate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 5h; Heating / reflux; | 100% |
With potassium carbonate In acetonitrile for 5h; Heating / reflux; | 100% |
With potassium carbonate In acetonitrile Reflux; | 98% |
ortho-nitrofluorobenzene
L-3-(2-thienyl)alanine
(S)-2-(2-nitrophenylamino)-3-(thiophen-2-yl)propanoic acid
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 20 - 100℃; for 16h; | 100% |
With potassium carbonate In ethanol; water at 20 - 100℃; for 16h; | 100% |
With potassium carbonate In ethanol; water at 100℃; for 16h; sealed tube; | 95% |
4-Trifluoromethoxyphenol
ortho-nitrofluorobenzene
1-nitro-2-[4 (trifluoromethoxy)phenoxy]benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 5h; Product distribution / selectivity; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid at 60℃; for 0.5h; | 100% |
With sulfuric acid; sulfur trioxide at 60℃; for 0.5h; | |
With chlorosulfonic acid at 80℃; for 10h; |
ortho-nitrofluorobenzene
(S)-2-(2-nitro-phenylamino)-pentanoic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; | 100% |
ortho-nitrofluorobenzene
Cyclopropylamine
cyclopropyl-(2-nitro-phenyl)-amine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 110℃; | 100% |
In dimethyl sulfoxide at 20 - 80℃; | 100% |
at 20℃; for 12h; | 90.3% |
The 1-Fluoro-2-nitrobenzene, with the CAS registry number 1493-27-2, is also known as 2-Fluoronitrobenzene. It belongs to the product categories of Benzene derivatives; Nitro Compounds; Nitrogen Compounds; Organic Building Blocks; Aryl Fluorinated Building Blocks; Building Blocks; C6; Chemical Synthesis; Fluorinated Building Blocks; Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks. Its EINECS number is 216-088-0. This chemical's molecular formula is C6H4FNO2 and molecular weight is 141.10. What's more, its systematic name is 1-Fluoro-2-nitrobenzene. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be ensured that the workshop is well ventilated or equipped with exhaust devices. It is used as intermediates in pesticide,medical and dye industries.
Physical properties of 1-Fluoro-2-nitrobenzene are: (1)ACD/LogP: 1.831; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.83; (4)ACD/LogD (pH 7.4): 1.83; (5)ACD/BCF (pH 5.5): 14.52; (6)ACD/BCF (pH 7.4): 14.52; (7)ACD/KOC (pH 5.5): 236.21; (8)ACD/KOC (pH 7.4): 236.21; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 45.82 Å2; (13)Index of Refraction: 1.534; (14)Molar Refractivity: 32.792 cm3; (15)Molar Volume: 105.485 cm3; (16)Polarizability: 13×10-24cm3; (17)Surface Tension: 42.8 dyne/cm; (18)Density: 1.338 g/cm3; (19)Flash Point: 94.444 °C; (20)Enthalpy of Vaporization: 44.655 kJ/mol; (21)Boiling Point: 228.863 °C at 760 mmHg; (22)Vapour Pressure: 0.1 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves.
You can still convert the following datas into molecular structure:
(1)SMILES: O=[N+]([O-])c1ccccc1F
(2)Std. InChI: InChI=1S/C6H4FNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H
(3)Std. InChIKey: PWKNBLFSJAVFAB-UHFFFAOYSA-N
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