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4-Chloronitrobenzene

4-Chloronitrobenzene
4-Chloronitrobenzene structure
CAS No.
100-00-5
Chemical Name:
4-Chloronitrobenzene
Synonyms
PNCB;NSC 9792;1-Chloro-4;un1578(dot);P-CHLORONITROBEZENE;p-Nitrochlorobenzol;p-Nitroclorobenzene;4-CHLORONITROBENZENE;4-NITROCHLOROBENZENE;P-NITROCHLOROBENZENE
CBNumber:
CB1726260
Molecular Formula:
C6H4ClNO2
Formula Weight:
157.55
MOL File:
100-00-5.mol

4-Chloronitrobenzene 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)
NIST Chemistry Reference
Benzene, 1-chloro-4-nitro-(100-00-5)
EPA Substance Registry System
Benzene, 1-chloro-4-nitro-(100-00-5)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H301+H311+H331-H320-H361-H370-H372-H301-H311-H331-H341-H351-H373-H411
Precautionary statements  P301+P310a-P501a-P261-P273-P280-P301+P310-P311-P201-P202-P260-P264-P270-P271-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P337+P313-P307+P311-P391-P403+P233-P405-P501
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
Toxicity LD50 (skin) for rats 16 gm/kg (quoted, RTECS, 1985).

NFPA 704

Diamond Hazard Value Description
1
2 3
Health   2 Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury (e.g. diethyl ether, ammonium phosphate, iodine)
Flammability   1 Materials that require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur. Includes some finely divided suspended solids that do not require heating before ignition can occur. Flash point at or above 93.3 °C (200 °F). (e.g. mineral oil, ammonia)
Instability   3 Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked (e.g. ammonium nitrate, cesium, hydrogen peroxide)
Special  

(NFPA, 2010)

4-Chloronitrobenzene price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C59122 1-Chloro-4-nitrobenzene 99% 100-00-5 100g $20 2018-11-13 Buy
Sigma-Aldrich 45925 1-Chloro-4-nitrobenzene analytical standard 100-00-5 250mg $35 2018-11-13 Buy
TCI Chemical C0222 4-Chloronitrobenzene >98.0%(GC) 100-00-5 25g $12 2018-11-22 Buy
TCI Chemical C0222 4-Chloronitrobenzene >98.0%(GC) 100-00-5 500g $24 2018-11-22 Buy
Alfa Aesar A15396 1-Chloro-4-nitrobenzene, 98+% 100-00-5 250g $18.8 2018-11-13 Buy

4-Chloronitrobenzene Chemical Properties,Uses,Production

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.

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.

4-Chloronitrobenzene Preparation Products And Raw materials

Raw materials

Preparation Products


4-Chloronitrobenzene Spectrum


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