Conditions | Yield |
---|---|
With nitric acid at 50℃; for 3h; | A 90.2% B 8.8% |
With nitric acid; sulfuric acid; sulfur trioxide In dichloromethane at 25℃; for 1.3h; Yield given. Yields of byproduct given; | |
With sulfuric acid; uronium nitrate at 25℃; for 24h; |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid; tetra-n-propylammonium bromate for 1.25h; Heating; | 88% |
With sodium perborate In acetic acid at 50 - 55℃; | 76% |
With sodium perborate In acetic acid at 50 - 60℃; for 2h; | 76% |
Conditions | Yield |
---|---|
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h; | 85% |
With 3,3-dimethyldioxirane Yield given; |
4-(dimethylamino)benzenediazonium tetrafluoroborate
A
N,N-dimethyl-aniline
B
1,2-Dinitrobenzene
C
N,N-dimethyl-4-[(2-nitrophenyl)diazenyl]aniline
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; | A 60% B 83% C 13% |
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in MeCN; | A 60% B 83% C 13% |
at -30℃; Mechanism; Product distribution; effect of solvents and 18-crown-6- additive; |
4-(dimethylamino)benzenediazonium tetrafluoroborate
A
N,N-dimethyl-aniline
B
3-nitro-4-hydroxy-4'-N,N-dimethylaminoazobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; | A 13% B 46% C 71% |
4-(dimethylamino)benzenediazonium tetrafluoroborate
A
N,N-dimethyl-aniline
B
3-nitro-4-hydroxy-4'-N,N-dimethylaminoazobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6; | A 13% B 46% C 71% |
4-methoxybenzenediazonium tetrafluoroborate
A
methoxybenzene
B
4-methoxy-3'-(2''-nitrobenzene-α-azoxy)-4'-hydroxyazobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6; | A 20% B 42% C 65% |
4-nitrobenzenediazonium tetrafluoroborate
A
3,4'-dinitro-4-hydroxyazobenzene
B
nitrobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; | A 58% B n/a C 63% |
4-nitrobenzenediazonium tetrafluoroborate
A
3,4'-dinitro-4-hydroxyazobenzene
B
nitrobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
In tetrahydrofuran at -30℃; for 1h; Product distribution; also in DMSO and in the presence of 18-crown-6; | A 58% B 27% C 63% |
copper(I) cyanide
2-nitro-aniline
A
nitrobenzene
B
o-nitrobenzonitrile
C
1,2-Dinitrobenzene
D
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With tert.-butylnitrite In dimethyl sulfoxide at 60℃; for 1.5h; | A 16% B 38% C 8% D 6% |
dimethylsulfone
2-nitro-aniline
A
methyl-(2-nitro-phenyl)-sulfoxide
B
nitrobenzene
C
1,2-Dinitrobenzene
D
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With tert.-butylnitrite; copper at 60℃; for 1.5h; Further byproducts given; | A 4% B 11% C 9% D 20% |
2-nitro-aniline
A
bis(2-nitrophenyl)amine
B
nitrobenzene
C
1,2-Dinitrobenzene
D
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With tert.-butylnitrite; copper In dimethyl sulfoxide at 60℃; for 1.5h; Further byproducts given; | A n/a B 11% C 9% D 20% |
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
With sulfuric acid; dihydrogen peroxide Product distribution; other reagents, other substituted benzofuroxans, var.time and temp.; | 13% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid |
Conditions | Yield |
---|---|
With ethanol; mixture of gaseous nitrogen oxides |
Conditions | Yield |
---|---|
With ethanol; mixture of gaseous nitrogen oxides | |
With tetrafluoroboric acid; N,N-dimethyl-formamide; sodium nitrite 1) water, 0 deg C, 2 h, 2) 20 deg C, 10 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
Thermodynamic data; |
Conditions | Yield |
---|---|
With nitric acid |
ortho-nitrobenzoic acid
A
2,5-dinitrobenzoic acid
B
2,3-di-nitrobenzoic acid
C
2,6-dinitrobenzoic acid
D
1,2-Dinitrobenzene
E
2,4-dinitrobenzoic acid
Conditions | Yield |
---|---|
With nitric acid; dinitrogen pentoxide at 25℃; Product distribution; addition of nitronium trifluoromethanesulphonate; |
nitrobenzene
A
meta-dinitrobenzene
B
para-dinitrobenzene
C
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
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; | |
With Nitrogen dioxide; ozone; methanesulfonic acid In dichloromethane at -10 - 0℃; for 9h; | A 91 % Chromat. B 1 % Chromat. C 8 % Chromat. |
nitrobenzene
A
meta-dinitrobenzene
B
para-dinitrobenzene
C
3-Chloronitrobenzene
D
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; nitric acid at 25℃; Product distribution; | A 96.4 % Chromat. B 1.0 % Chromat. C 1.2 % Chromat. D 1.3 % Chromat. |
Conditions | Yield |
---|---|
In acetone for 6h; Product distribution; Ambient temperature; other primary amines; | 65 % Chromat. |
In acetone for 6h; Ambient temperature; protected from light; | 65 % Chromat. |
Conditions | Yield |
---|---|
In acetone for 6h; Ambient temperature; | 85 % Chromat. |
Conditions | Yield |
---|---|
In chloroform at 24℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With sodium nitrite In water at 25 - 29.9℃; Kinetics; |
Conditions | Yield |
---|---|
With 1,3-dihydro-2H-benzimidazole-2-thione radical cation In acetonitrile at 23℃; Kinetics; Oxidation; |
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
With copper(I) oxide; water; sodium nitrite |
1,2-Dinitrobenzene
Conditions | Yield |
---|---|
With water; copper; sodium nitrite at 20℃; |
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 palladium 10% on activated carbon; ammonium formate; silica gel In methanol for 1.5h; Milling; | 99% |
With sodium tetrahydroborate In water at 90℃; | 99% |
With hydrazine hydrate In ethanol at 20℃; for 4h; chemoselective reaction; | 98% |
Conditions | Yield |
---|---|
With borax; N-Acetylcysteine In methanol; water for 2h; Ambient temperature; | 99% |
ethyl 2-cyanoacetate
1,2-Dinitrobenzene
(+/-)-ethyl cyano(2-nitrophenyl)acetate
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide 1.) 10 min, 2.) 90 deg C, 0.5 h; | 99% |
1,2-Dinitrobenzene
2-Aminophenyl disulfide
2-(2-nitro)phenylthiophenylamine
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: 1,2-Dinitrobenzene In N,N-dimethyl-formamide at 50℃; for 0.166667h; | 99% |
4-fluorobenzaldehyde
1,2-Dinitrobenzene
2-(4-fluorophenyl)-1H-benzoimidazole
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With hydrogen at 20℃; under 760.051 Torr; for 1h; | 98% |
With hydrogen; 1-(2-benzimidazolyl)-C(CH3)=NH-NHCSNH2-Pd(II) In tetrahydrofuran at 20℃; for 2h; atmospheric pressure; | 95% |
With triethylamine In water at 80℃; for 2h; Inert atmosphere; Green chemistry; chemoselective reaction; | 95% |
Conditions | Yield |
---|---|
With borax; N-Acetylcysteine In methanol; water for 5h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 98% |
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; | 98% |
With formic acid; Au/TiO2-R In water at 120℃; for 6h; Green chemistry; chemoselective reaction; | 87% |
thiophene-2-carbaldehyde
1,2-Dinitrobenzene
2-(2-thienyl)-1H-benzimidazole
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With caesium carbonate In hexane; dimethyl sulfoxide | 97% |
Conditions | Yield |
---|---|
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction; | 97% |
With palladium particles distributed over the surface of fibrous silica nanospheres modified via aminopropyltriethoxysilane In tetrahydrofuran at 70℃; for 3h; | 96 %Chromat. |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 97% |
2-methylphenyl aldehyde
1,2-Dinitrobenzene
2-(2-methylphenyl)benzimidazole
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With titanium(IV) oxide for 4h; Irradiation; | 96% |
With oxalic acid; titanium(IV) oxide; β‐cyclodextrin In water for 5h; Inert atmosphere; Irradiation; Green chemistry; | 88 %Chromat. |
Conditions | Yield |
---|---|
With zinc phthalocyanine; hydrazine hydrate In PEG-400 at 100℃; for 8h; | 96% |
Conditions | Yield |
---|---|
95% |
Conditions | Yield |
---|---|
With potassium permanganate at -7℃; for 0.166667h; | 95% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 25℃; for 0.166667h; Inert atmosphere; Microwave irradiation; Anhydrous conditions; | 95% |
para-thiocresol
1,2-Dinitrobenzene
2-(4-methylphenylsulfanyl)nitrobenzene
Conditions | Yield |
---|---|
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h; | 94% |
In N,N-dimethyl acetamide electrolyse, catholyte N(Et)4ClO4; | 66% |
m-bromobenzoic aldehyde
1,2-Dinitrobenzene
2-(3-bromo-phenyl)-1H-benzoimidazole
Conditions | Yield |
---|---|
Stage #1: 1,2-Dinitrobenzene With methyl 3-amino-5-(2-(4-methoxyphenyl)acetamido)benzoate; water at 20℃; for 2h; Stage #2: m-bromobenzoic aldehyde With oxygen at 60℃; for 12h; | 94% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 94% |
4-methoxy-benzaldehyde
1,2-Dinitrobenzene
2-(4-methoxyphenyl)-1H-benzimidazole
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 70℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 94% |
1-naphthaldehyde
1,2-Dinitrobenzene
2-(naphthalen-1-yl)-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 100℃; under 7500.75 Torr; for 20h; Temperature; Autoclave; Green chemistry; | 94% |
With hydrogen In ethyl acetate at 100℃; under 7500.75 Torr; for 20h; Autoclave; | 94% |
Conditions | Yield |
---|---|
With hydrogen In ethyl acetate at 130℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 94% |
With hydrogen In ethyl acetate at 130℃; under 7500.75 Torr; for 20h; Autoclave; | 94% |
Trimethyl(methylthio)silane
1,2-Dinitrobenzene
methyl 2-nitrophenyl sulfide
Conditions | Yield |
---|---|
Stage #1: 1,2-Dinitrobenzene With caesium carbonate In dimethyl sulfoxide Stage #2: Trimethyl(methylthio)silane In dimethyl sulfoxide at 20℃; for 16h; | 93% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 48h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With titanium(IV) oxide for 4h; Irradiation; | 92% |
MF: C6H4N2O4
MW: 168.11
EINECS: 208-431-8
Density: 1.486 g/cm3
Flash Point: 150 °C
Stability: Highly reactive
Melting Point: 116-119 ºC
IUPAC Name: 1,2-dinitrobenzene
Water Solubility: 150 mg/L (20 ºC)
Appearance: Colorless to yellow solid
Enthalpy of Vaporization: 53.92 kJ/mol
Boiling Point: 319.9 °C at 760 mmHg
Vapour Pressure: 0.000614 mmHg at 25°C
Air & Water: Reactions Slowly mixes with water.
Synonyms: 1,2-Dinitro-benzen ; 1,2-Dinitrobenzol ; Benzene, o-dinitro- ; Benzene,1,2-dinitro- ; Benzene,1,2-dinitro-(9CI) ; Benzene,o-dinitro- ; NSC60682 ; O-dinitro-benzen
Following is the molecular structure of O-dinitrobenzen (528-29-0):
O-dinitrobenzen (528-29-0)is used for the synthesis of dyestuffs, dyestuff intermediates, explosives, and celluloid production.
Reactivity Profile of O-dinitrobenzen (528-29-0): 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 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.
Suspected carcinogen. Poison by inhalation and ingestion. Moderately toxic by skin contact. Can cause liver, kidney, and central nervous system injury. Combustible when exposed to heat or flame; can react vigorously with oxidizing materials. A severe explosion hazard when shocked or exposed to heat or flame. It is used in bursting charges and to fill artillery shells. Mixtures with nitric acid are highly explosive. To fight fire, use water, CO2, dry chemical. Dangerous; when heated to decomposition it emits highly toxic fumes of NOx and explodes.
Safety Information of O-dinitrobenzen (528-29-0):
Hazard Codes: T+,N
T+: Very Toxic N: Dangerous for the environment
Risk Statements: 26/27/28-33-50/53
26/27/28: Very Toxic by inhalation, in contact with skin and if swallowed
33: Danger of cumulative effects
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 28-36/37-45-60-61-28A
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: CZ7450000
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29042000
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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