1,2-Dichloro-4-nitrobenzene

Last updated
1,2-Dichloro-4-nitrobenzene
1,2-Dichloro-4-nitrobenzene.png
Names
Preferred IUPAC name
1,2-Dichloro-4-nitrobenzene
Other names
DCNB, 3,4-dichloronitrobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.513 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-764-2
PubChem CID
RTECS number
  • CZ5250000
UNII
UN number 2811 1578
  • InChI=1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H Yes check.svgY
    Key: NTBYINQTYWZXLH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H
    Key: NTBYINQTYWZXLH-UHFFFAOYAQ
  • Clc1ccc(cc1Cl)[N+]([O-])=O
Properties
C6H3Cl2NO2
Molar mass 192.01
Appearancecolourless to yellow needles
Density 1.4588 g/cm3
Melting point 52.8 to 56 °C (127.0 to 132.8 °F; 325.9 to 329.1 K)
Boiling point 263 °C (505 °F; 536 K)
organic solvents
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H302, H336, H361, H372, H373, H411
P201, P202, P260, P261, P264, P270, P271, P273, P281, P301+P312, P304+P340, P308+P313, P312, P314, P330, P391, P403+P233, P405, P501
Flash point 124 °C (255 °F; 397 K)
420 °C (788 °F; 693 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2-Dichloro-4-nitrobenzene is an organic compound with the formula 1,2-Cl2C6H3-4-NO2. This pale yellow solid is related to 1,2-dichlorobenzene by the replacement of one H atom with a nitro functional group. This compound is an intermediate in the synthesis of agrochemicals.

Production and uses

The nitration of 1,2-dichlorobenzene mainly produces 1,2-dichloro-4-nitrobenzene, together with smaller amounts of the 3-nitro isomer. It can also be prepared by chlorination of 1-chloro-4-nitrobenzene. [1]

One of the chlorides is reactive toward nucleophiles. Potassium fluoride gives 2-chloro-1-fluoro-4-nitrobenzene, an intermediate in the production of herbicides. With ammonia, one obtains 2-chloro-4-nitroaniline, a precursor to diazo dyes. Reduction with iron powder gives 3,4-dichloroaniline (m.p. 72 °C, CAS# 95-76-1). [1]

Related Research Articles

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

IARC group 2B substances, mixtures and exposure circumstances are those that have been classified as "possibly carcinogenic to humans" by the International Agency for Research on Cancer (IARC) as This category is used when there is limited evidence of carcinogenicity in humans and less than sufficient evidence of carcinogenicity in experimental animals. It may also be used when there is insufficient evidence of carcinogenicity in humans but sufficient evidence in experimental animals. In some cases, an agent, mixture, or exposure circumstance with inadequate evidence of carcinogenicity in humans but limited evidence in experimental animals, combined with supporting evidence from other relevant data, may be included in this group.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

IARC group 3 substances, chemical mixtures and exposure circumstances are those that can not be classified in regard to their carcinogenicity to humans by the International Agency for Research on Cancer (IARC). This category is used most commonly for agents, mixtures and exposure circumstances for which the level of evidence of carcinogenicity is inadequate in humans and inadequate or limited in experimental animals. Exceptionally, agents (mixtures) for which the evidence of carcinogenicity is inadequate in humans, but sufficient in experimental animals may be placed in this category when there is strong evidence that the mechanism of carcinogenicity in experimental animals does not operate in humans. Agents, mixtures and exposure circumstances that do not fall into any other group are also placed in this category.

A dichlorodifluoroethylene is one of three compounds with the chemical formula C
2
Cl
2
F
2
. Dichlorodifluoroethylenes are colourless gases, and are some of the simplest chlorodifluoroalkenes.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 CFR 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

<span class="mw-page-title-main">4-Aminophenol</span> Chemical compound

4-Aminophenol (or para-aminophenol or p-aminophenol) is an organic compound with the formula H2NC6H4OH. Typically available as a white powder, it is commonly used as a developer for black-and-white film, marketed under the name Rodinal.

<span class="mw-page-title-main">4-Nitroaniline</span> Chemical compound

4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.

<span class="mw-page-title-main">Propanil</span> Chemical compound

Propanil is a widely used contact herbicide. With an estimated use of about 8 million pounds in 2001, it is one of the more widely used herbicides in the United States. Propanil is said to be in use in approximately 400,000 acres of rice production each year.

Dichloronitrobenzene can refer to any of the following isomers of C6H3Cl2(NO2):

The molecular formula C6H3Cl2NO2 (molar mass: 192.01 g/mol) may refer to:

<span class="mw-page-title-main">Disperse Yellow 26</span> Chemical compound

Disperse Yellow 26, or 4-chloro-2-nitrodiphenylamine, is a disperse dye. The dye is used in polyamide and vinegar fiber dyeing. Disperse Yellow 26 is produced by the condensation of aniline and 1,4-dichloro-2-nitrobenzene.

<span class="mw-page-title-main">1,4-Dichloro-2-nitrobenzene</span> Chemical compound

1,4-Dichloro-2-nitrobenzene is an organic compound with the formula C6H3Cl2NO2. One of several isomers of dichloronitrobenzene, it is a yellow solid that is insoluble in water. It is produced by nitration of 1,4-dichlorobenzene. It is a precursor to many derivatives of commercial interest. Hydrogenation gives 1,4-dichloroaniline. Nucleophiles displace the chloride adjacent to the nitro group: ammonia gives the aniline derivative, aqueous base gives the phenol derivative, and methoxide gives the anisole derivative. These compounds are respectively 4-chloro-2-nitroaniline, 4-chloro-2-nitrophenol, and 4-chloro-2-nitroanisole.

<span class="mw-page-title-main">2,5-Dichloroaniline</span> Chemical compound

2,5-Dichloroaniline is an organic compound with the formula C6H3Cl2NH2. One of six isomers of dichloroaniline, it is a colorless solid that is insoluble in water. It is produced by hydrogenation of 1,4-dichloro-2-nitrobenzene. It is a precursor to dyes and pigments, e.g., Pigment Yellow 10.

In chemistry, the Halex process is used to convert aromatic chlorides to the corresponding aromatic fluorides. The process entails Halide exchange, hence the name. The reaction conditions call for hot (150-250 °C) solution of the aryl chloride and anhydrous potassium fluoride. Typical solvents are dimethylsulfoxide, dimethylformamide, and sulfolane. Potassium chloride is generated in the process. The reaction is mainly applied to nitro-substituted aryl chlorides. Sometimes more soluble fluorides, such as caesium fluoride and TBAF are used.

Niobium(III) chloride also known as niobium trichloride is a compound of niobium and chlorine. The binary phase NbCl3 is not well characterized but many adducts are known.

<span class="mw-page-title-main">1,8-Naphthalic anhydride</span> Chemical compound

1,8-Naphthalic anhydride is an organic compound with the formula C10H6(C2O3). It is one of three isomers of naphthalic anhydride, the other two being the 1,2- and the 2,3-derivatives. The 1,8-isomer is prepared by aerobic oxidation of acenaphthene. 2,6-naphthalenedicarboxylic acid can be prepared from this anhydride. 1,8-Naphthalic anhydride is a precursor to the 4-chloro and 4,5-dichloro derivatives. These chloride groups are susceptible to displacement by amines and alkoxides, giving rise, ultimately, to a large family of naphthalimides, which are used as optical brighteners.

The Cadogan–Sundberg indole synthesis, or simply Cadogan indole synthesis, is a name reaction in organic chemistry that allows for the generation of indoles from o-nitrostyrenes with the use of trialkyl phosphites, such as triethyl phosphite.

References

  1. 1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005.