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Cas Database

Name	p-DINITROBENZENE	EINECS	N/A
CAS No.	100-25-4	Density	1.486g/cm³
PSA	91.64000	LogP	2.54940
Solubility	Soluble in water. (0.8 g/L) at 20°C.	Melting Point	170-173 °C(lit.)
Formula	C6H4 N2 O4	Boiling Point	183.4 °C34 mm Hg(lit.)
Molecular Weight	168.109	Flash Point	154.4°C
Transport Information	N/A	Appearance	light yellow powder
Safety	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 NO_x. See also o- and m-DINITROBENZENE.	Risk Codes	26/27/28-33-34-50/53
Molecular Structure		Hazard Symbols	A suspected carcinogen and poison by ingestion. TWA 0.15 ppm (skin). Mixture with nitric acid is a high explosive.
Synonyms	Benzene,p-dinitro- (8CI); 1,4-Dinitrobenzene; NSC 3809; Para-dinitrobenzene;p-Dinitrobenzene	Article Data	144

p-DINITROBENZENE Synthetic route

: 98-95-3
nitrobenzene

: 100-25-4
para-dinitrobenzene

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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%

: 4612-26-4
1,4-Phenyldiboronic acid

: 100-25-4
para-dinitrobenzene

Conditions

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%

: 71-43-2
benzene

A: 99-65-0
meta-dinitrobenzene

B: 100-25-4
para-dinitrobenzene

Conditions

Conditions	Yield
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

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;

: 106-50-3
1,4-phenylenediamine

: 100-25-4
para-dinitrobenzene

Conditions

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

: 74087-85-7
3,3-dimethyldioxirane

: 624-18-0
benzene-1,4-diamine hydrochloride

: 100-25-4
para-dinitrobenzene

Conditions

Conditions	Yield
In water; acetone for 23h; Ambient temperature;	82%

: 905718-45-8
[(4-nitrophenyl)(phenyl)iodonium trifluoromethanesulfonate]

: 100-25-4
para-dinitrobenzene

Conditions

Conditions	Yield
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 NO_x.
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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