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{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 392102521 | verifiedrevid = 477223140
| Name = 4-nitrochlorobenzene | Name = 4-nitrochlorobenzene
| ImageFile = 4-chloronitrobenzene.png | ImageFileL1 = 4-chloronitrobenzene.png
| ImageSize = 150px
| ImageSizeL1 = 145
⚫ | IUPACName = 1-Chloro-4-nitrobenzene
| ImageAltL1 = Skeletal formula of 4-nitrochlorobenzene
⚫ | OtherNames = 4-Chloro-1-nitrobenzene; 4-Chloronitrobenzene; ''p''-Nitrochlorobenzene; PNCBO
| ImageFileR1 = 4-Nitrochlorobenzene-3D-balls.png
⚫ | Section1 = {{Chembox Identifiers
| ImageSizeR1 = 105
⚫ | SMILES = ClC1=CC=C(()=O)C=C1
| ImageAltR1 = Ball-and-stick model of the 4-nitrochlorobenzene molecule
| CASNo = 100-00-5
⚫ | PIN = 1-Chloro-4-nitrobenzene
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | OtherNames = 4-Chloro-1-nitrobenzene<br />4-Chloronitrobenzene<br />''p''-Nitrochlorobenzene<br />PNCBO
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID = 7194
| PubChem = | CASNo = 100-00-5
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | RTECS =
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = CVL66U249D
| PubChem = 7474
⚫ | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | ChemSpiderID = 21106020
⚫ | SMILES = C1=CC(=CC=C1(=O))Cl
| InChI = 1/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H
| InChIKey = CZGCEKJOLUNIFY-UHFFFAOYAO
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CZGCEKJOLUNIFY-UHFFFAOYSA-N
⚫ | RTECS =
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C14456 | KEGG = C14456
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=6|H=4|O=2|N=1|Cl=1 | C=6 | H=4 | O=2 | N=1 | Cl=1
| Appearance = Light yellow solid | Appearance = Light yellow solid
| Odor = sweet<ref name=PGCH/>
| Density = 1.52 g/cm³ (20 °C) | Density = 1.52 g/cm<sup>3</sup> (20 °C)
| Solubility = Insoluble | Solubility = Insoluble
| SolubleOther = Soluble in toluene, ether, acetone, hot ethanol | SolubleOther = Soluble in toluene, ether, acetone, hot ethanol
| Solvent = other solvents | Solvent = other solvents
| MeltingPtC = 83.6
| BoilingPtC = 242.0 | MeltingPtC = 83.6
| pKa = | BoilingPtC = 242.0
| Viscosity = | pKa =
| Viscosity =
| Dipole = | Dipole =
| RefractIndex = | RefractIndex =
| VaporPressure = 0.2 mmHg (30°C)<ref name=PGCH/>
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = 12 °C | NFPA-H =
| RPhrases = | NFPA-F =
| SPhrases = | NFPA-R =
| NFPA-H = | AutoignitionPtC =
| NFPA-F = | FlashPtC = 12
| LD50 = 812 mg/kg (rat, oral)<br/>1414 mg/kg (mouse, oral)<br/>440 mg/kg (mouse, oral)<br/>420 mg/kg (rat, oral)<ref name=PGCH/>
| NFPA-R =
| PEL = TWA 1 mg/m<sup>3</sup> <ref name=PGCH>{{PGCH|0452}}</ref>
| Autoignition =
| IDLH = Ca <ref name=PGCH/>
| FlashPt =
| LC50 = 164 mg/m<sup>3</sup> (cat, 7 hr)<ref name=PGCH/>
| LD50 =
| REL = Ca<ref name=PGCH/>
}} }}
}} }}


'''4-Nitrochlorobenzene''' is the ] with the formula ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>. This compound is a light yellow crystalline solid that is stable to air. 4-Nitrochlorobenzene is a common intermediate in the industrial production of a number of compounds, including common antioxidants found in rubber. '''4-Nitrochlorobenzene''' is the ] with the formula ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including ]s commonly found in ]. Other ]s with the formula ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> include ] and 3-nitrochlorobenzene.


==Preparation== ==Preparation==
4-Nitrochlorobenzene is prepared industrially by nitration of ]:
⚫ 4-Nitrochlorobenzene was originally prepared by the ] of 4 bromochlorobenzene by Holleman and coworkers<ref>The nitration of mixed dihalogen benzenes. Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.</ref>:
:{{chem2|ClC6H5 + HNO3 -> ClC6H4NO2 + H2O}}


⚫ This reaction affords both the 2- and the 4-nitro derivatives, in about a 1:2 ratio. These isomers are separated by a combination of crystallization and distillation.<ref name=Ullmann/> 4-Nitrochlorobenzene was originally prepared by the ] of 4-bromochlorobenzene by Holleman and coworkers.<ref>"The nitration of mixed dihalogen benzenes" Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.</ref>
:]


⚫ ==Applications==
Currently, 4-nitrochlorobenzene is prepared on an industrial scale from chlorobenzene via ] using ] or ] catalysts:<ref>Zhang, Cun; Liu, Tao; Ma, Chunyan. U.S. Patent 10,235,242, 2008.</ref>
4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives. ] gives ], and ]. Reduction with iron metal gives ]. The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to ], unlike related chlorobenzene. Thus, the strong ]s hydroxide, ], ], and ] displace chloride to give respectively ], 4-nitroanisole, ], and ].<ref name=Ullmann>{{cite encyclopedia|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411|isbn=978-3527306732}}</ref><ref>{{cite journal |doi=10.15227/orgsyn.014.0066 |title=p-Nitrodiphenyl Ether |journal=Organic Syntheses |year=1934 |volume=14 |page=66|first1=Ray Q.|last1=Brewster|first2=Theodore |last2=Groening }}</ref>


⚫ Another use of 4-nitrochlorobenzene is its condensation with aniline to produce 4-nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber.
:]


] drug ] (4-aniline).<ref name=Ullmann/>]]
⚫ ==Applications==
{{clear left}}
4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives, including ], ], ], ], ], and ].<ref name=Ullmann>Nitro Compounds, Aromatic. ''Ullmann's Encyclopedia of Industrial Chemistry'', 7th Ed.; Wiley & Sons: New York, 1997; pp. 18-19</ref> These reactions mainly involve the nucleophilic displacement of chloride . The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to ], unlike related chlorobenzene.


==Safety==
⚫ Another major use of 4-nitrochlorobenzene is its condensation with aniline to produce 4 nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber.<ref name=Ullmann/>
The U.S. ] considers 4-nitrochlorobenzene as a potential occupational carcinogen.<ref></ref> The ] set a permissible exposure limit of 1 mg/m<sup>3</sup> The ] recommends an airborne exposure limit of 0.64 mg/m<sup>3</sup> over a time-weighted average of eight hours.<ref></ref><ref></ref>

:]


==References== ==References==
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{{DEFAULTSORT:Nitrochlorobenzene, 4-}} {{DEFAULTSORT:Nitrochlorobenzene, 4-}}
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Latest revision as of 09:07, 9 September 2024

4-nitrochlorobenzene
Skeletal formula of 4-nitrochlorobenzene
Ball-and-stick model of the 4-nitrochlorobenzene molecule
Names
Preferred IUPAC name 1-Chloro-4-nitrobenzene
Other names 4-Chloro-1-nitrobenzene
4-Chloronitrobenzene
p-Nitrochlorobenzene
PNCBO
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.554 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4HKey: CZGCEKJOLUNIFY-UHFFFAOYSA-N
  • InChI=1/C6H4ClNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4HKey: CZGCEKJOLUNIFY-UHFFFAOYAO
SMILES
  • C1=CC(=CC=C1(=O))Cl
Properties
Chemical formula C6H4ClNO2
Molar mass 157.55 g·mol
Appearance Light yellow solid
Odor sweet
Density 1.52 g/cm (20 °C)
Melting point 83.6 °C (182.5 °F; 356.8 K)
Boiling point 242.0 °C (467.6 °F; 515.1 K)
Solubility in water Insoluble
Solubility in other solvents Soluble in toluene, ether, acetone, hot ethanol
Vapor pressure 0.2 mmHg (30°C)
Hazards
Flash point 12 °C (54 °F; 285 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 812 mg/kg (rat, oral)
1414 mg/kg (mouse, oral)
440 mg/kg (mouse, oral)
420 mg/kg (rat, oral)
LC50 (median concentration) 164 mg/m (cat, 7 hr)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 1 mg/m
REL (Recommended) Ca
IDLH (Immediate danger) Ca
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.

Preparation

4-Nitrochlorobenzene is prepared industrially by nitration of chlorobenzene:

ClC6H5 + HNO3 → ClC6H4NO2 + H2O

This reaction affords both the 2- and the 4-nitro derivatives, in about a 1:2 ratio. These isomers are separated by a combination of crystallization and distillation. 4-Nitrochlorobenzene was originally prepared by the nitration of 4-bromochlorobenzene by Holleman and coworkers.

Applications

4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives. Nitration gives 2,4-dinitrochlorobenzene, and 3,4-dichloronitrobenzene. Reduction with iron metal gives 4-chloroaniline. The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to nucleophilic aromatic substitution, unlike related chlorobenzene. Thus, the strong nucleophiles hydroxide, methoxide, fluoride, and amide displace chloride to give respectively 4-nitrophenol, 4-nitroanisole, 4-fluoronitrobenzene, and 4-nitroaniline.

Another use of 4-nitrochlorobenzene is its condensation with aniline to produce 4-nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber.

4-Nitrochlorobenzene is the precursor to the anti-leprosy drug Dapsone (4-aniline).

Safety

The U.S. National Institute for Occupational Safety and Health considers 4-nitrochlorobenzene as a potential occupational carcinogen. The Occupational Safety and Health Administration set a permissible exposure limit of 1 mg/m The American Conference of Governmental Industrial Hygienists recommends an airborne exposure limit of 0.64 mg/m over a time-weighted average of eight hours.

References

  1. ^ NIOSH Pocket Guide to Chemical Hazards. "#0452". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
  3. "The nitration of mixed dihalogen benzenes" Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.
  4. Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses. 14: 66. doi:10.15227/orgsyn.014.0066.
  5. CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): p-nitrochlorobenzene
  6. CDC - NIOSH Pocket Guide to Chemical Hazards
  7. New Jersey Department of Health and Senior Services - Hazardous Substance Fact Sheet
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