1,3-Dichlorobenzene

Last updated
1,3-Dichlorobenzene
M-Dichlorbenzol.svg
Names
Preferred IUPAC name
1,3-Dichlorobenzene
Other names
m-Dichlorobenzene; meta-Dichlorobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.994 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H
    Key: ZPQOPVIELGIULI-UHFFFAOYSA-N
  • InChI=1/C6H4Cl2/c7-5-2-1-3-6(8)4-5/h1-4H
    Key: ZPQOPVIELGIULI-UHFFFAOYAZ
  • ClC1=CC=CC(Cl)=C1
Properties
C6H4Cl2
Molar mass 147.00 g·mol−1
AppearanceColorless liquid
Density 1.288 g/cm3
Melting point −22 to −25 °C (−8 to −13 °F; 251 to 248 K)
Boiling point 172 to 173 °C (342 to 343 °F; 445 to 446 K)
Insoluble
-83.19·10−6 cm3/mol
Hazards
Flash point 65 °C (149 °F; 338 K)
Related compounds
Related compounds
1,3-Dibromobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Dichlorobenzene (also known as meta-dichlorobenzene) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. It is the least common of the three isomers of dichlorobenzene, and it is a colorless liquid that is insoluble in water. It is produced as a minor byproduct of the chlorination of benzene, but can also be prepared in a directed manner by the Sandmeyer reaction of 3-chloroaniline. It also arises from the isomerization of the other dichlorobenzenes at high temperature. [1]

Hazards

This chemical is combustible. "Hazardous decomposition products" are carbon monoxide, carbon dioxide, chlorine, hydrogen chloride gas. It is toxic to aquatic life with long-lasting effects. [2]

Related Research Articles

In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.

<span class="mw-page-title-main">Petrochemical</span> Chemical product derived from petroleum

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

Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.

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

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

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

Chlorobenzene 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.

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

Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane is far less stable than benzene. The carbon (and hydrogen) atoms of the prismane molecule are arranged in the shape of a six-atom triangular prism—this compound is the parent and simplest member of the prismanes class of molecules. Albert Ladenburg proposed this structure for the compound now known as benzene. The compound was not synthesized until 1973.

Chlorotoluenes are aryl chlorides based on toluene in which at least one aromatic hydrogen atom is replaced with a chlorine atom. They have the general formula C7H8–nCln, where n = 1–5 is the number of chlorine atoms.

Hexachlorobenzene, or perchlorobenzene, is an aryl chloride and a six-substituted chlorobenzene with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.

A chlorophenol is any organochloride of phenol that contains one or more covalently bonded chlorine atoms. There are five basic types of chlorophenols and 19 different chlorophenols in total when positional isomerism is taken into account. Chlorophenols are produced by electrophilic halogenation of phenol with chlorine.

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

Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. It is an amber oily liquid.

Chlorobenzenes are a group of aryl chlorides/halobenzenes consisting of one or more chlorine atoms as substituents on a benzene core. They have the formula C6H6–nCln, where n = 1–6 is the number of chlorine atoms. Depending on the number of chlorine substituents, there may be several constitutional isomers possible.

<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.

1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.

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

Hexachlorocyclohexane (HCH), C
6
H
6
Cl
6
, is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. This structure has nine stereoisomers, which differ by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees.

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.

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

Pentachlorobenzene (PeCB) is an aryl chloride and a five-substituted chlorobenzene with the molecular formula C6HCl5 which is a chlorinated aromatic hydrocarbon. It consists of a benzene ring substituted with five chlorine atoms. PeCB was once used industrially for a variety of uses, but because of environmental concerns there are currently no large scale uses of PeCB. Pentachlorobenzene is a known persistent organic pollutant (POP) and banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.

1,2,3-Trichlorobenzene is an organochlorine compound with the chemical formula C6H3Cl3. This is one of three isomers of trichlorobenzene; the two others are 1,2,4-Trichlorobenzene and 1,3,5-Trichlorobenzene.

References

  1. U. Beck, E. Löser "Chlorinated Benzenes and other Nucleus-Chlorinated Aromatic Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi : 10.1002/14356007.o06_o03
  2. "SAFETY DATA SHEET". Thermo Fisher Scientific. Retrieved 9 February 2021.