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p-DINITROBENZENE
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  • Name p-DINITROBENZENE
  • EINECSN/A
  • CAS No. 100-25-4
  • Density1.486g/cm3
  • PSA91.64000
  • LogP2.54940
  • SolubilitySoluble in water. (0.8 g/L) at 20°C.
  • Melting Point170-173 °C(lit.)
  • FormulaC6H4 N2 O4
  • Boiling Point183.4 °C34 mm Hg(lit.)
  • Molecular Weight168.109
  • Flash Point154.4°C
  • Transport InformationN/A
  • Appearancelight yellow powder
  • SafetySuspected 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. See also o- and m-DINITROBENZENE.
  • Risk Codes26/27/28-33-34-50/53
  • Molecular Structure
    Molecular Structure of 100-25-4 (1,4-DINITROBENZENE)
  • Hazard SymbolsA suspected carcinogen and poison by ingestion. TWA 0.15 ppm (skin). Mixture with nitric acid is a high explosive.
  • SynonymsA suspected carcinogen and poison by ingestion. TWA 0.15 ppm (skin). Mixture with nitric acid is a high explosive.
  • Article Data144

p-DINITROBENZENE Synthetic route

98-95-3

nitrobenzene

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
With dinitrogen monoxide at 8℃; under 2250.23 Torr; Reagent/catalyst; Autoclave;98.4%

(4-nitrophenyl)(phenyl)iodonium tetrafluoroborate

A

636-98-6

p-nitrobenzene iodide

B

100-25-4

para-dinitrobenzene

C

591-50-4

iodobenzene

D

98-95-3

nitrobenzene

Conditions
ConditionsYield
With sodium nitrite In chloroform; water at 56℃; for 1h;A 1%
B 98%
C 93 % Chromat.
D 1 % Chromat.
105-12-4

p-dinitrosobenzene

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
With dihydrogen peroxide In trifluoroacetic acid for 10h; Ambient temperature;95%
With dihydrogen peroxide; trifluoroacetic acid
100-01-6

4-nitro-aniline

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
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%
4612-26-4

1,4-Phenyldiboronic acid

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
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%
71-43-2

benzene

A

99-65-0

meta-dinitrobenzene

B

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
With Perfluorooctanesulfonic acid; nitric acid; ytterbium(III) perfluorooctanesulfonate In hexane at 60℃; for 16h;A 90%
B 8%
98-95-3

nitrobenzene

A

99-65-0

meta-dinitrobenzene

B

100-25-4

para-dinitrobenzene

C

528-29-0

1,2-Dinitrobenzene

Conditions
ConditionsYield
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;
106-50-3

1,4-phenylenediamine

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
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
74087-85-7

3,3-dimethyldioxirane

624-18-0

benzene-1,4-diamine hydrochloride

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
In water; acetone for 23h; Ambient temperature;82%
905718-45-8

[(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate]

100-25-4

para-dinitrobenzene

Conditions
ConditionsYield
With sodium nitrite In ethyl acetate at 70℃; for 16h; Temperature; Solvent; Sealed tube;82%

p-DINITROBENZENE Chemical Properties

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-DINITROBENZENE Uses

 P-Dinitrobenzen (100-25-4) is used in organic synthesis.

p-DINITROBENZENE Production

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.

p-DINITROBENZENE Toxicity Data With Reference

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.

p-DINITROBENZENE Consensus Reports

Reported in EPA TSCA Inventory.

p-DINITROBENZENE Safety Profile

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
 

p-DINITROBENZENE Standards and Recommendations

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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