Chlorobenzene
General
Systematic name	chlorobenzene
Other names	benzene chloride monochlorobenzene Phenyl chloride
Molecular formula	C6H5Cl
SMILES	ClC1=CC=CC=C1
Molar mass	112.56 g/mol
Appearance	colorless liquid
CAS number	[108-90-7]
Properties
Density and phase	1.11 g/cm3, liquid
Solubility in water	low
Other solvents	most organic solvents
Melting point	-45 °C (228 K)
Boiling point	131 °C (404 K)
Refractive index (nD20)	1.525
Viscosity	? cP at ? °C
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	29 °C
R/S statement	R: 10 20 51/53 S: 24/25 61
RTECS number	CZ0175000
Related compounds
Related compounds	benzene 1,4-dichlorobenzene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Chlorobenzene is an aromatic organic compound with the chemical formula C₆H₅Cl. It is a colorless, flammable liquid first made in 1851 by reacting phenol and phosphorus pentachloride.^{[citation needed]} Image File history File links Size of this preview: 346 × 599 pixelsFull resolution (809 × 1400 pixel, file size: 12 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... Image File history File links Size of this preview: 462 × 599 pixelsFull resolution (1608 × 2086 pixel, file size: 248 KB, MIME type: image/png) File historyClick on a date/time to view the file as it appeared at that time. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... This article does not cite any references or sources. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... Viscosity is a measure of the resistance of a fluid to deform under shear stress. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... Benzene is an organic chemical compound with the formula C6H6. ... R-phrases , , S-phrases , , , , Flash point 66 °C RTECS number CZ4550000 Supplementary data page Structure and properties n, εr, etc. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Benzene is the simplest of the arenes, a family of organic compounds An organic compound is any member of a large class of chemical compounds whose molecules contain carbon and hydrogen; therefore, carbides, carbonates, carbon oxides and elementary carbon are not organic (see below for more on the definition controversy... 1851 (MDCCCLI) was a common year starting on Wednesday (see link for calendar) of the Gregorian calendar (or a common year starting on Friday of the 12-day-slower Julian calendar). ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... Phosphorus pentachloride is the chemical compound with the formula PCl5. ...

Uses

Chlorobenzene has been used in the manufacture of certain pesticides, most notably DDT by reaction with chloral (trichloroacetaldehyde). It once found use in the production of phenol. Today the major use of chlorobenzene is as an intermediate in the production of nitrochlorobenzenes and diphenyl oxide, which are important in the production of commodities such as herbicides, dyestuffs, and rubber. Chlorobenzene is also used as a high-boiling solvent in organic synthesis as well as many industrial applications. A cropduster spreading pesticide. ... DDT or Dichloro-Diphenyl-Trichloroethane is the first modern pesticide and is one of the best known synthetic pesticides. ... Chloral is a colourless narcotic liquid, obtained at first by the action of chlorine on alcohol; treated with water it produces chloral hydrate. ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Organic synthesis is the construction of organic molecules via chemical processes. ...

Synthesis

Chlorobenzene is prepared by chlorination of benzene, usually in the presence of a catalytic amount of Lewis acid such as ferric chloride: In organic chemistry, an electrophilic aromatic halogenation is a type of halogenation. ... In chemistry, a Lewis acid can accept a pair of electrons and form a coordinate covalent bond, after the American chemist Gilbert Lewis. ... Ferric chloride (FeCl3) is an iron-based salt. ...

C₆H₆ + Cl₂ → C₆H₅Cl + HCl

Because chlorine is electronegative, PhCl exhibits decreased susceptibility to to attack by other electrophiles. For this reason, the chlorination process produces only small amounts of dichloro- and trichlorobenzenes.

External links