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4-Chloronitrobenzene

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4-Chloronitrobenzene Basic information

Product Name:
4-Chloronitrobenzene
CAS:
100-00-5
MF:
C6H4ClNO2
MW:
157.55
EINECS:
202-809-6
Mol File:
100-00-5.mol
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4-Chloronitrobenzene Chemical Properties

Melting point:
80-83 °C(lit.)
Boiling point:
242 °C(lit.)
Density 
1.298 g/mL at 25 °C(lit.)
vapor density 
5.4 (vs air)
vapor pressure 
0.09 mm Hg ( 25 °C)
refractive index 
1.5376 (estimate)
Flash point:
>230 °F
solubility 
Soluble in acetone and alcohol (Weast, 1986)
form 
Crystals or Flakes
color 
Yellow
Water Solubility 
Insoluble
Merck 
14,2151
BRN 
508691
Henry's Law Constant
4.90 x 10-6 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
Exposure limits
Potential occupational carcinogen. NIOSH REL: IDLH 100; OSHA PEL: TWA 1.
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, hydroxides. Reacts violently with sodium methoxide in methanol.
InChIKey
CZGCEKJOLUNIFY-UHFFFAOYSA-N
CAS DataBase Reference
100-00-5(CAS DataBase Reference)
IARC
2B (Vol. 65, 123) 2020
NIST Chemistry Reference
Benzene, 1-chloro-4-nitro-(100-00-5)
EPA Substance Registry System
p-Chloronitrobenzene (100-00-5)
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Safety Information

Hazard Codes 
T,N
Risk Statements 
23/24/25-40-48/20/21/22-51/53-68
Safety Statements 
28-36/37-45-61-28A
RIDADR 
UN 1578 6.1/PG 2
WGK Germany 
2
RTECS 
CZ1050000
Autoignition Temperature
500 °F
Hazard Note 
Very Toxic
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29049085
Hazardous Substances Data
100-00-5(Hazardous Substances Data)
Toxicity
LD50 (skin) for rats 16 gm/kg (quoted, RTECS, 1985).

MSDS

  • Language:EnglishProvider:PNCB
  • Language:EnglishProvider:SigmaAldrich
  • Language:EnglishProvider:ACROS
  • Language:EnglishProvider:ALFA
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4-Chloronitrobenzene Usage And Synthesis

Chemical Properties

light yellow crystals

Chemical Properties

p-Chloronitrobenzene is extensively used in different industries as an intermediate in the manufacture of dyes, rubber, and agricultural chemicals. It is incompatible with strong oxidizers and alkalis

Chemical Properties

p-Nitrochlorobenzene is a yellow crystalline solid with a sweet odor.

Uses

In dye chemistry.

Uses

p-Nitrochlorobenzene is largely used to produce p-nitrophenol with smaller production of p-nitroaniline.

Production Methods

The annual production of p-CNB in the United States in 1993 was 35,000 metric tons and on the order of 50,000–70,000 metric tons in Germany. It is used as an intermediate in the manufacture of dyes, rubber, and agricultural chemicals.
Human exposure may occur to dyestuff workers but the extent is uncertain because of its use as a chemical intermediate. p-Chloronitrobenzene has been detected in the surface water of the Rhine River at a concentration range of 0.1–6.38 mg/L.

Production Methods

p-Nitrochlorobenzene is made by the nitration of chlorobenzene.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 2407, 1987 DOI: 10.1021/jo00388a014
Tetrahedron Letters, 19, p. 4519, 1978

General Description

Light yellow crystalline solid. Density 1.520 g / cm3. Melting point 83°C. Sweet odor. Very toxic by inhalation, ingestion, and skin absorption. p-Chloronitrobenzene is extensively used in different industries as an intermediate in the manufacture of dyes, rubber, and agricultural chemicals. It is incompatible with strong oxidisers and alkalis.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Chloronitrobenzene reacts with oxidizing agents. Reacts violently and finally explosively when added to a solution of sodium methoxide in methanol. . Unstable when heated.

Hazard

A questionable carcinogen. Very toxic by inhalation and ingestion. Absorbed via skin. Combustible. Methemoglobinemia.

Health Hazard

Repeated exposure to high levels of p-chloronitrobenzene causes adverse health effects. The symptoms of toxicity include, but are not limited to, anoxia, unpleasant taste, anemia, methemoglobinemia, hematuria (blood in the urine), spleen, kidney, bone marrow changes, and reproductive effects. The target organs of p-chloronitrobenzene poisoning have been identifi ed as the blood, liver, kidneys, cardiovascular system, spleen, bone marrow, and reproductive system.

Fire Hazard

4-Chloronitrobenzene is combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic data. A poison by ingestion. Experimental reproductive effects. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. May explode on heating. Potentially violent reaction with sodium methoxide. When heated to decomDosition it emits very toxic fumes of NOx and Cl-. See also other chloronitrobenzene entries and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Potential Exposure

p-Nitrochlorobenzene (PNCB) is used as an intermediate in pesticide (parathion) manufacture, drug (phenacetin and acetaminophen) manufacture; and in dye making; rubber and antioxidant manufacture.

Environmental Fate

Biological. Under aerobic conditions, the yeast Rhodosporidium sp. metabolized pchloronitrobenzene to 4-chloroacetanilide and 4-chloro-2-hydroxyacetanilide as final major metabolites. Intermediate compounds identified include 4-chloronitrosobenzene, 4-chlorophenylhydroxylamine, and 4-chloroaniline (Corbett and Corbett, 1981).
Under continuous flow conditions involving feeding, aeration, settling, and reflux, a mixture of p-chloronitrobenzene and 2,4-dinitrochlorobenzene was reduced 61–70% after 8–13 d by Arthrobacter simplex, a microorganism isolated from industrial waste. A similar experiment was conducted using two aeration columns. One column contained A. simplex, the other a mixture of A. simplex and microorganisms isolated from soil (Streptomyces coelicolor, Fusarium sp., probably aquaeductum and Trichoderma viride). After 10 d, 89.5–91% of the nitro compounds was reduced. p-Chloronitrobenzene was reduced to 4-chloroaniline and six unidentified compounds (Bielaszczyk et al., 1967).
Photolytic. An aqueous solution containing p-chloronitrobenzene and a titanium dioxide (catalyst) suspension was irradiated with UV light (λ >290 nm). 2-Chloro-5-nitrophenol was the only compound identified as a minor degradation product. Continued irradiation caused additional degradation yielding carbon dioxide, water, hydrochloric and nitric acids (Hustert et al., 1987).
Irradiation of p-chloronitrobenzene in air and nitrogen produced 4-chloro-2-nitrophenol and 4- chlorophenol, respectively (Kanno and Nojima, 1979).
Chemical. Although no products were identified, p-chloronitrobenzene (1.5 x 10-5 M) was reduced by iron metal (33.3 g/L acid washed 18–20 mesh) in a carbonate buffer (1.5 x 10-2 M) at pH 5.9 and 15 °C. Based on the pseudo-first-order disappearance rate of 0.0336/min, the half-life was 20.6 min (Agrawal and Tratnyek, 1996).

Shipping

UN1578 Chloronitrobenzenes, solid or liquid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise the nitrobenzene from 95% EtOH (charcoal) and sublime it in vacuo. [Emmons JAm Chem Soc 76 3470 1954, Newman & Forrest J Am Chem Soc 69 1221 1947, Beilstein 5 IV 723.]

Incompatibilities

A strong oxidizer. Reacts violently with oxidizers, combustibles, alkalis, sodium methoxide; and reducing materials.

Waste Disposal

Incineration (816℃, 0.5 second for primary combustion; 1204℃, 1.0 second for secondary combustion). The formation of elemental chlorine can be prevented through injection of steam or methane into the combustion process. nitrogen oxides may be abated through the use of thermal or catalytic devices.

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