Conditions | Yield |
---|---|
With dinitrogen monoxide at 8℃; under 2250.23 Torr; Reagent/catalyst; Autoclave; | 98.4% |
A
p-nitrobenzene iodide
B
para-dinitrobenzene
C
iodobenzene
D
nitrobenzene
Conditions | Yield |
---|---|
With sodium nitrite In chloroform; water at 56℃; for 1h; | A 1% B 98% C 93 % Chromat. D 1 % Chromat. |
Conditions | Yield |
---|---|
With dihydrogen peroxide In trifluoroacetic acid for 10h; Ambient temperature; | 95% |
With dihydrogen peroxide; trifluoroacetic acid |
Conditions | Yield |
---|---|
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h; | 95% |
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; | 92% |
With tert.-butylhydroperoxide; 3 A molecular sieve; zirconium(IV) tert-butoxide In dichloromethane for 2.5h; Ambient temperature; | 88% |
Conditions | Yield |
---|---|
With nitric acid In 1,2-dichloro-ethane at 70℃; for 16h; Inert atmosphere; | 95% |
With nitric acid; trifluoroacetic acid In water at 80℃; for 18h; regioselective reaction; | 63% |
Conditions | Yield |
---|---|
With Perfluorooctanesulfonic acid; nitric acid; ytterbium(III) perfluorooctanesulfonate In hexane at 60℃; for 16h; | A 90% B 8% |
nitrobenzene
A
meta-dinitrobenzene
B
para-dinitrobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
With Iron(III) nitrate nonahydrate; phosphorus pentoxide In neat (no solvent) at 20℃; for 6h; Milling; Green chemistry; Overall yield = 98 percent; | A 86% B 3% C 9% |
With nitronium hexafluorophosphate In nitromethane for 0.166667h; Product distribution; Ambient temperature; var. nitrating agents, var. solv., var. temp., rel. rate of the nitration; | A 86.9 % Chromat. B 1.9 % Chromat. C 11.1 % Chromat. |
With methanesulfonic acid; Nitrogen dioxide; ozone In dichloromethane at -10 - 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; | 82% |
With trifluoroacetyl peroxide In dichloromethane at -5 - 5℃; for 1h; | 77% |
With tert.-butylhydroperoxide; 3 A molecular sieve; zirconium(IV) tert-butoxide In dichloromethane for 4.5h; Ambient temperature; | 72% |
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 10h; Reflux; | 56% |
With dichloromethane; dihydrogen peroxide; trifluoroacetic anhydride |
3,3-dimethyldioxirane
benzene-1,4-diamine hydrochloride
para-dinitrobenzene
Conditions | Yield |
---|---|
In water; acetone for 23h; Ambient temperature; | 82% |
[(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate]
para-dinitrobenzene
Conditions | Yield |
---|---|
With sodium nitrite In ethyl acetate at 70℃; for 16h; Temperature; Solvent; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With ammonium heptamolybdate; dihydrogen peroxide In methanol at 60℃; for 96h; | 76% |
With Nitrogen dioxide In tetrachloromethane; dichloromethane at 24.9℃; Rate constant; Thermodynamic data; Ea, A, ΔH(excit.), ΔS(excit.); |
4-nitrophenylboronic acid
para-dinitrobenzene
Conditions | Yield |
---|---|
With 1,3-disulfonic acid imidazolium nitrate In neat (no solvent) at 20℃; for 0.05h; | 75% |
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Inert atmosphere; Schlenk technique; | 51% |
Conditions | Yield |
---|---|
With potassium nitrite In water at 20℃; for 0.5h; | 74% |
4-nitrobenzenediazonium tetrafluoroborate
A
para-dinitrobenzene
B
formaldehyd
C
4-nitro-phenol
D
nitrobenzene
Conditions | Yield |
---|---|
With sodium nitrite In methanol at 0℃; for 0.0333333h; Further byproducts given; | A 12% B 51% C 4% D 60% E n/a |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ammonium iodide; water In dimethyl sulfoxide at 90℃; for 4h; Sealed tube; | 59% |
1,2,4-trinitrobenzene
A
meta-dinitrobenzene
B
para-dinitrobenzene
C
2,4-Dinitrophenol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate In methanol at 60℃; for 75h; | A 35% B 24% C 22% |
dimethylsulfone
4-nitro-aniline
A
para-dinitrobenzene
B
p-nitrophenyl methyl sulfoxide
C
nitrobenzene
D
4-nitrobenzonitrile
Conditions | Yield |
---|---|
With tert.-butylnitrite at 50℃; for 1.5h; Title compound not separated from byproducts; | A 7% B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With sodium nitrite | |
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 80 °C / Sealed tube 2: sodium nitrite / ethyl acetate / 16 h / 70 °C / Sealed tube View Scheme |
Conditions | Yield |
---|---|
With sodium nitrite |
p-benzoquinone dioxime
para-dinitrobenzene
Conditions | Yield |
---|---|
With nitric acid | |
With sodium hypochlorite | |
With diethyl ether; dinitrogen tetraoxide |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid | |
With dihydrogen peroxide; acetic acid |
Conditions | Yield |
---|---|
With ethanol; mixture of gaseous nitrogen oxides |
para-dinitrobenzene
Conditions | Yield |
---|---|
With copper(I) sulfate; copper(II) sulfate; sodium nitrite |
para-dinitrobenzene
Conditions | Yield |
---|---|
With copper; sodium nitrite |
2,3-Dichloro-1,4-naphthoquinone
p-Dinitrobenzol-Monoradikalanion
A
para-dinitrobenzene
B
2,3-Dichlor-1,4-naphthosemichinon
Conditions | Yield |
---|---|
In gas at 150℃; Rate constant; | |
at 149.9℃; Thermodynamic data; Equilibrium constant; |
3,5-dinitrobenzonitrile
p-Dinitrobenzol-Monoradikalanion
A
para-dinitrobenzene
Conditions | Yield |
---|---|
at 149.9℃; Thermodynamic data; Equilibrium constant; |
2,6-dichloro-1,4-benzoquinone
p-Dinitrobenzol-Monoradikalanion
A
para-dinitrobenzene
B
2,6-dichloro-p-benzoquinone anion radical
Conditions | Yield |
---|---|
In gas at 150℃; Rate constant; |
4-methoxybenzenediazonium tetrafluoroborate
A
para-dinitrobenzene
B
4-methoxy-N-(4-nitrophenyl)aniline
C
methoxybenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 0.166667h; | A 0.92 g B 0.35 g C 0.16 g |
4-methoxybenzenediazonium tetrafluoroborate
A
para-dinitrobenzene
B
4-methoxy-N-(4-nitrophenyl)aniline
C
methoxybenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 0.166667h; Product distribution; | A 0.92 g B 0.35 g C 0.16 g |
Conditions | Yield |
---|---|
With formic acid In acetonitrile at 20℃; for 1h; Irradiation; | 100% |
In water at 25℃; for 0.333333h; Sonication; | 99% |
With sodium tetrahydroborate In water at 95℃; for 0.333333h; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water at 50℃; for 0.0833333h; Green chemistry; | 100% |
With hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 3h; chemoselective reaction; | 100% |
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 3h; Sonication; chemoselective reaction; | 99% |
para-dinitrobenzene
tetrathiafulvalene
1,4-Dinitro-benzene; compound with [2,2']bi[[1,3]dithiolylidene]
Conditions | Yield |
---|---|
In toluene Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In water; dimethyl sulfoxide for 144h; Mechanism; var. solvent DMSO/water ratios; further bromo- and chloronitro- and dinitrobenzenes; isotope labelling experiments; | 100% |
para-dinitrobenzene
4-Methoxybenzenethiol
4-(4-methoxyphenylsulfanyl)nitrobenzene
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 25℃; for 0.166667h; Inert atmosphere; Darkness; | 100% |
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h; | 92% |
para-dinitrobenzene
para-thiocresol
4-nitrophenyl 4-methylphenyl sulfide
Conditions | Yield |
---|---|
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; Solvent; | 99% |
In N,N-dimethyl acetamide electrolyse, catolyte N(Et)4ClO4; | 77% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Catalytic behavior; | 99% |
With 2C15H23N3O2*2Cu(2+)*4ClO4(1-)*5H2O; potassium carbonate In ethanol at 80℃; for 8h; Catalytic behavior; Green chemistry; | 97% |
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; | 94% |
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; Schlenk technique; | 93% |
para-dinitrobenzene
4-methoxy-phenol
1-methoxy-4-(4-nitrophenoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Catalytic behavior; | 99% |
With 2C15H23N3O2*2Cu(2+)*4ClO4(1-)*5H2O; potassium carbonate In ethanol at 80℃; for 8h; Catalytic behavior; Green chemistry; | 98% |
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction; | 99% |
para-dinitrobenzene
2-Aminophenyl disulfide
2-aminophenyl 4-nitrophenyl sulfide
Conditions | Yield |
---|---|
Stage #1: 2-Aminophenyl disulfide With ammonium hydroxide; L-Cysteine In N,N-dimethyl-formamide at 50℃; for 0.0166667h; pH=9; Inert atmosphere; Stage #2: para-dinitrobenzene In N,N-dimethyl-formamide at 50℃; for 0.166667h; | 99% |
para-dinitrobenzene
2,2,2-trifluoroethanol
1-(2,2,2-trifluoroethoxy)-4-nitrobenzene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; | 98% |
para-dinitrobenzene
Trimethyl(methylthio)silane
1-methylthio-4-nitro-benzene
Conditions | Yield |
---|---|
Stage #1: para-dinitrobenzene With caesium carbonate In dimethyl sulfoxide Stage #2: Trimethyl(methylthio)silane In dimethyl sulfoxide at 20℃; for 16h; | 98% |
Conditions | Yield |
---|---|
With potassium tert-butylate In ammonia at -70℃; for 0.333333h; | 97.6% |
Conditions | Yield |
---|---|
With potassium tert-butylate In ammonia at -70℃; for 1h; Product distribution; with/without base additive (KNH2); | 97% |
With potassium tert-butylate In ammonia at -70℃; for 1h; | 97% |
4-methyleneoxetan-2-one
para-dinitrobenzene
N-(4-nitrophenyl)-3-oxobutanamide
Conditions | Yield |
---|---|
In chloroform at 10 - 65℃; for 2h; | 96% |
Conditions | Yield |
---|---|
Stage #1: para-dinitrobenzene With sodium tetrahydroborate In ethyl acetate Stage #2: ethyl acetate With bis(dimethylglyoximato)copper(II) for 4h; Reflux; | 96% |
para-dinitrobenzene
4-nitroaniline hydrochloride
Conditions | Yield |
---|---|
Stage #1: para-dinitrobenzene With iron(III) acetylacetonate; 1,1,3,3-Tetramethyldisiloxane In tetrahydrofuran at 60℃; for 48h; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 0.0833333h; | 95% |
Stage #1: para-dinitrobenzene With iododioxobis(triphenylphosphine)rhenium(V); Dimethylphenylsilane In toluene for 24h; Reflux; Stage #2: With hydrogenchloride In diethyl ether; toluene regioselective reaction; | 58% |
Conditions | Yield |
---|---|
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; | 95% |
para-dinitrobenzene
4-t-butylbenzenethiol
(4-(tert-butyl)phenyl)(4-nitrophenyl)sulfane
Conditions | Yield |
---|---|
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; | 94% |
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; Schlenk technique; | 82% |
Conditions | Yield |
---|---|
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2h; Catalytic behavior; | 94% |
Conditions | Yield |
---|---|
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h; | A 93% B 2% |
With D-glucose; bakers' yeast In phosphate buffer; ethanol at 30℃; for 0.5h; pH=6.5; Product distribution; Further Variations:; time; | A 83% B n/a |
With sodium tetrahydroborate; selenium In ethanol at 23 - 26℃; for 0.25h; | A 81% B 16% |
With 1,2-bis(mercaptomethyl)benzene; (Et4N) In acetonitrile at 26℃; for 1.5h; Product distribution; |
para-dinitrobenzene
ethyl 2-cyanoacetate
ethyl α-cyano-α-(p-nitrophenyl)acetate
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide 1.) 10 min, 2.) 90 deg C, 0.5 h; | 93% |
MF: C6H4N2O4
MW: 168.11
EINECS: 202-833-7
Flash Point: 154.4 °C
Storage temp: 2-8°C
Index of Refraction: 1.612
Melting Point: 170-173 °C(lit.)
IUPAC Name: 1,4-dinitrobenzene
Density: 1.625 g/mL at 25 °C(lit.)
Enthalpy of Vaporization: 51.83 kJ/mol
Boiling Point: 299.9 °C at 760 mmHg
Vapour Pressure: 0.00206 mmHg at 25°C
Appearance: Pale-white or yellow solid.
Air & Water Reactions: Slowly mixes with water.
Stability: Stable, but may be shock-sensitive. May explode if heated. Incompatible with oxidizing agents, strong bases, nitric acid, many metals, tin oxides.
Synonyms: 1,4-Dinitrobenzen ; 1,4-Dinitrobenzenn ; P-Dinitrobenzen ; 1,4-Dinitro-benzen ; Benzene, p-dinitro- ; Benzene,1,4-dinitro- ; Dithane a-4 ; Dithanea-4
Following is the molecular structure of P-Dinitrobenzen (100-25-4):
P-Dinitrobenzen (100-25-4) is used in organic synthesis.
Reactivity Profile All three isomers have similar properties and may react vigorously with oxidizing materials. Their reaction with nitric acid (nitration) will lead to a mixture of trinitrobenzenes possessing high-explosive properties. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive. 1,2-dinitrobenzene (100-25-4) is a severe explosion hazard when shocked or exposed to heat or flame. When heated to decomposition all dinitrobenzens emit toxic fumes of nitrogen oxides.
1. | mmo-sat 5 µg/plate | CRNGDP Carcinogenesis. 6 (1985),727. | ||
2. | mma-sat 25 µg/plate | CRNGDP Carcinogenesis. 6 (1985),727. | ||
3. | orl-cat LDLo:29 mg/kg | 85ESA3 Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals. 11 (1989),516. |
Reported in EPA TSCA Inventory.
Suspected carcinogen. Poison by ingestion. Mutation data reported. Mixture with nitric acid is a high explosive. When heated to decomposition it emits toxic fumes of NOx.
Safety Information of P-Dinitrobenzen (100-25-4):
Hazard Codes: T+,N
T+: Very Toxic N: Dangerous for the environment
Risk Statements: 26/27/28-33-34-50/53
26/27/28: Very Toxic by inhalation, in contact with skin and if swallowed
33: Danger of cumulative effects
34: Causes burns
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 28-36/37-45-60-61
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37: Wear suitable protective clothing and gloves
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60: This material and/or its container must be disposed of as hazardous waste
61: Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR: UN 3443 6.1/PG 2
WGK Germany: 3
RTECS: CZ7525000
HazardClass: 6.1
PackingGroup: II
OSHA PEL: TWA 1 mg/m3 (skin)
ACGIH TLV: TWA 0.15 ppm (skin)
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification: 6.1; Label: Poison
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