1,4-DINITROBENZENE Chemical Properties

Melting point:

170-173 °C(lit.)

Boiling point:

183.4 °C34 mm Hg(lit.)

Density 

1.625 g/mL at 25 °C(lit.)

vapor pressure 

2.25 x 10^-4 mmHg at 35 °C (Hine et al., 1963)

refractive index 

1.725 (589.3 nm)

Flash point:

150 °C

storage temp. 

Store below +30°C.

solubility 

alcohol: soluble1g in 300ml

form 

Crystals or Powder

color 

Ochre to orange

Water Solubility 

Soluble in water. (0.8 g/L) at 20°C.

Merck 

14,3273

BRN 

1105828

Henry's Law Constant

4.79(x 10^-7 atm?m³/mol) at 35 °C (approximate - calculated from water solubility and vapor pressure)

Exposure limits

NIOSH REL: TWA 1, IDLH 50; OSHA PEL: TWA 1 ACGIH TLV: TWA 0.15 ppm for all isomers (adopted).

Stability:

Stable, but may be shock-sensitive. May explode if heated. Incompatible with oxidizing agents, strong bases, nitric acid, many metals, tin oxides.

CAS DataBase Reference

100-25-4(CAS DataBase Reference)

EPA Substance Registry System

p-Dinitrobenzene (100-25-4)

Safety Information

Hazard Codes 

T+,N,T,F

Risk Statements 

26/27/28-33-34-50/53-52/53-39/23/24/25-23/24/25-11

Safety Statements 

28-36/37-45-60-61-16

RIDADR 

UN 3443 6.1/PG 2

OEB

C

OEL

TWA: 1 mg/m3 [skin]

WGK Germany 

3

RTECS 

CZ7525000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29042090

Hazardous Substances Data

100-25-4(Hazardous Substances Data)

Toxicity

IC50 (24-h) for river bacteria 1.27 mg/L (Yuan and Lang, 1997).

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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1,4-DINITROBENZENE Usage And Synthesis

Chemical Properties

light yellow powder

Physical properties

Clear, colorless to white crystalline solid or monoclinic crystals. Slowly turns yellow on exposure to air.

Uses

1,4-Dinitrobenzene is used in a study to evaluate the ionization mechanism and solvent effect by novel atmospheric pressure photoionization mass spectrometry in negative ion mode for analysis of some compounds. 1,4-Dinitrobenzene can be used in synthesis of dyes and dye intermediates.

Uses

manufacture of dyes, dye intermediates, explosives, plastics.

Definition

ChEBI: A dinitrobenzene carrying nitro groups at positions 1 and 4.

General Description

Colorless to yellow solid. Sinks and mixes slowly with water.

Air & Water Reactions

Slowly mixes with water.

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 [Urbanski, 1967, vol. 3, p. 290]. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur [Anon., J. R. Inst. Chem., 1960, 84, p. 451]. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive [Urbanski, 1964, vol. 1, 592]. 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 [Sax, 9th ed., 1996, p. 1374].

Health Hazard

INHALATION OR INGESTION: Headache, vertigo, nausea, vomiting, diarrhea, fever, rapid weak pulse, decreased blood pressure, cyanosis, exhaustion, hepatomegaly, jaundice, albuminurea, hematuria, visual scotomata, amblyopia and nystagmus. EYES: Irritation. SKIN: Stains skin yellow; if skin contact is prolonged, can be absorbed into blood causing same symptoms as for inhalation.

Safety Profile

Suspected carcinogen. Poison by ingestion. Mutation data reported. Mxture with nitric acid is a high explosive. When heated to decomposition it emits toxic fumes of NOx. See also 0and mDINITROBENZENE

Environmental Fate

Biological. In activated sludge inoculum, following a 20-d adaptation period, no biodegradation was observed (Pitter, 1976).
Photolytic. Low et al. (1991) reported that the nitro-containing compounds (e.g., 2,4- dinitrophenol) undergo degradation by UV light in the presence of titanium dioxide yielding ammonium, carbonate, and nitrate ions. By analogy, 1,4-dinitrobenzene should degrade forming identical ions.
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987). 1,4-Dinitrobenzene will not hydrolyze in water (Kollig, 1993).

Purification Methods

Crystallise 1,4-dinitrobenzene from EtOH or EtOAc. Dry it under vacuum over P2O5. It can be sublimed in a vacuum. [Beilstein 5 IV 741.]

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