100-00-5 Usage
Uses
Used in Chemical Industry:
4-Chloronitrobenzene is used as an intermediate for the production of various chemicals, including dyes, rubber, and agricultural chemicals. It plays a crucial role in the synthesis of different compounds and materials.
Used in Pharmaceutical Industry:
4-Chloronitrobenzene is used as a starting material for the synthesis of drugs such as finasteride and paracetamol. It is also an important intermediate in the production of azo dyes and sulfide dyes.
Used in Pesticide Industry:
4-Chloronitrobenzene is used as a raw material for the manufacturing of the herbicide pesticide.
Used in Rubber Industry:
4-Chloronitrobenzene is used as a raw material for the production of rubber antioxidant 4010, which is essential for enhancing the durability and performance of rubber products.
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/jo00388a014Tetrahedron Letters, 19, p. 4519, 1978
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.
Carcinogenicity
No increase in tumor incidence was seen
in rats fed up to 1000 ppm in the diet for 2
years; in mice, results were equivocal, with
high-dose animals showing an increase in vascular
tumors and low-dose males showing an
increase in liver tumors.6 The IARC has determined
that there is inadequate evidence in
experimental animals and humans for the carcinogenicity
of chlorobenzenes.7
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.
Check Digit Verification of cas no
The CAS Registry Mumber 100-00-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 100-00:
(5*1)+(4*0)+(3*0)+(2*0)+(1*0)=5
5 % 10 = 5
So 100-00-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H
100-00-5Relevant articles and documents
Natural bentonite clay/dilute HNO3 (40%) - A mild, efficient, and reusable catalyst/reagent system for selective mono nitration and benzylic oxidations
Bahulayan, Damodaran,Narayan, Gopinathan,Sreekumar, Vellalath,Lalithambika, Malathy
, p. 3565 - 3574 (2002)
Selective mono nitration of Aromatic hydrocarbons and benzylic oxidations can be achieved in high yield using reusable catalyst/reagent system consisting of bentonite clay and dilute HNO3 under relatively mild experimental conditions. The dual behavior of the catalyst reagent system is utilized for the regioselective synthesis of a variety of industrially important compounds.
Nitration of aromatic compounds by Zn(NO3)2· 2N2O4 and its charcoal-supported system
Iranpoor, Nasser,Firouzabadi, Habib,Heydari, Reza,Shiri, Morteza
, p. 263 - 270 (2005)
Zn(NO3)2·N2O4 and its charcoal supported system were found to be efficient nitrating agents. Mononitration of aromatic compounds such as benzene, alkyl benzenes, halobenzenes, nitrobenzene, anisol, and the highly selective mono-, di-, and trinitration of phenol, and dinitraion of substituted phenols were also performed in the presence of these reagents.
Polymer-supported ytterbium perfluorooctanesulfonate [Yb(OPf)3]: A recyclable catalyst for organic reactions
Yi, Wen-Bin,Cai, Chun
, p. 524 - 528 (2008)
Amberlyst A-21, a kind of well-known and cheap polymeric material, was treated with ytterbium perfluorooctanesulfonate [Yb(OPf)3] giving a reagent with a ytterbium loading of 1.34 (wt%). The polymer-supported fluorous ytterbium catalyses the highly efficient nitration, esterification, Fridel-Crafts acylation, and aldol condensation. The catalyst can be recovered by simple filtration and used again without a significant loss of catalytic activity. The protocol avoids the use of fluorous solvents during the reaction or workup, which are expensive and can leach in small amounts.
Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions
Earle, Martyn J.,Katdare, Suhas P.,Seddon, Kenneth R.
, p. 707 - 710 (2004)
It has been an unproven paradigm that the choice of which ionic liquid to use in a chemical reaction can have a dramatic effect on the outcome of that chemical reaction. We demonstrate, for the first time, that the reaction of toluene and nitric acid in three different ionic liquids gives rise to three completely different products in high yield. Furthermore, ionic liquids can catalyze these reactions with the only byproduct being water.
Preparation of heteropoly acid based amphiphilic salts supported by nano oxides and their catalytic performance in the nitration of aromatics
Wang, Peng-Cheng,Yao, Kai,Lu, Ming
, p. 2197 - 2202 (2013)
A series of Keggin heteropoly acid anion based amphiphilic salts supported by nano oxides were synthesized and used as catalysts in the nitration of aromatic compounds with HNO3. The reaction conditions in the nitration of toluene were optimized and both 92.6% conversion and good para selectivity (ortho:para = 1.09) were obtained.
STIMULATION BY Sn(2+) OR ASCORBIC ACID ON DIAZONIUM SALTS REACTIONS
Galli, Carlo
, p. 4515 - 4516 (1980)
Use of a mild reducing agent and ligand transfer for the transformation of diazonium salts into aryl halides provides an alternative to the Sandmeyer procedure.
Silver-catalysed protodecarboxylation of ortho-substituted benzoic acids
Cornella, Josep,Sanchez, Carolina,Banawa, David,Larrosa, Igor
, p. 7176 - 7178 (2009)
Catalytic amounts of Ag(i) salts in DMSO have been found to promote the protodecarboxylation of a wide variety of ortho-substituted benzoic acids under mild conditions and in excellent yields, highlighting a possible role for silver in decarboxylative cross-couplings. The Royal Society of Chemistry 2009.
Reactions of Aryl Diazonium Salts and Arylazo Alkyl Ethers. 7. Kinetic Studies of the Decomposition of Z Ethers Derived from Some Substituted 2-Nitrobenzene Diazonium Salts
Broxton, Trevor J.,McLeish, Michael J.
, p. 3673 - 3679 (1982)
Rate constans for the decomposition of (Z)-syn ethers derived from some 4- or 5-substituted 2-nitrobenzenediazonium salts have been measured in both basic ethanol.For some compounds the rate of decomposition is independent of the base concetration while for others the rate is first order in base concetration.Solvent and substituent effects poit to the base-independent mechanism occuring on the free diazonium salt formed by ionization of the Z ether while the base-dependent mechanism occurs on the Z ether itself.Mechanisms are proposed for each of these reactions.
Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts
Lee, Young Min,Moon, Mi Eun,Vajpayee, Vaishali,Filimonov, Victor D.,Chi, Ki-Whan
, p. 7418 - 7422 (2010)
Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.
Electrophilic Aromatic Nitration Using a Mixed Catalyst of Lithium, Molybdenum, Ytterbium on Silica Gel
Shi, Min,Cui, Shi-Cong
, p. 1329 - 1333 (2003)
A novel mixed catalyst of LiClO4 (15% w/w), Yb(OPf)3 (15% w/w, Pf = perfluorooctanesulfonyl), MoO3 (15% w/w) on silica gel for electrophilic aromatic nitration reaction has been explored. The nitration reactions were accomplished by this mixed catalyst and nitric acid under solvent-free conditions. Moreover, the mixed catalyst can be easily recovered from the aqueous layer by heating in an oven and reused for the next nitration reaction.
