Dichloromethane
IUPAC name	Dichloromethane
Other names	Methylene chloride, methylene dichloride, Solmethine, Narkotil, Solaesthin, Di-clo, Freon 30, R-30, DCM, UN 1593
Identifiers
CAS number	75-09-2
PubChem	6344
EINECS number	200-838-9
KEGG	C02271
ChEBI	15767
RTECS number	PA8050000
SMILES	C(Cl)Cl
InChI	InChI=1/CH2Cl2/c2-1-3/h1H2
Properties
Molecular formula	CH2Cl2
Molar mass	84.93 g/mol
Appearance	Colorless liquid
Density	1.3255 g/cm³, liquid
Melting point	-96.7 °C (175.7 K) Image File history File links Molecular Structure of Dichloromethane (commonly called Methylene Chloride) H Padleckas created this image file on June 14, 2005 especially for use in the article Dichloromethane in Wikimedia. ... Image File history File links Size of this preview: 713 × 600 pixelsFull resolution (1100 × 925 pixel, file size: 193 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. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... KEGG PATHWAY Database is one of the important databases in bioinformatics. ... ChEBI (meaning Chemical Entities of Biological Interest, or Chemistry at the EBI) is a database of molecular entities focused on small chemical compounds. ... 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. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	39 °C (312.8 K) Italic text This article is about the boiling point of liquids. ...
Solubility in water	13 g/l at 20 °C
Vapor pressure	47 kPa at 20 ºC
Hazards
MSDS	External MSDS
Main hazards	Harmful (Xn), Carc. Cat. 2B
NFPA 704	Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... Vapor pressure is the pressure of a vapor in equilibrium with its non-vapor phases. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... Please find below supplementary chemical data about dichloromethane. ... The examples and perspective in this article or section may not represent a worldwide view. ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 1 2 0
R-phrases	R40
S-phrases	S23, S24/25, S36/37
Flash point	None
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Near IR absorption spectrum of dichloromethane showing complicated overlapping overtones of mid IR absorption features.

Dichloromethane (DCM) or methylene chloride is the chemical compound with the formula CH₂Cl₂. It is a colorless, volatile liquid with a moderately sweet aroma. It is widely used as a solvent, the general view being that it is one of the less harmful of the chlorocarbons, and it is miscible with most organic solvents. 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. ... For other uses, see Flash point (disambiguation). ... Please find below supplementary chemical data about dichloromethane. ... Please find below supplementary chemical data about dichloromethane. ... 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. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... Please find below supplementary chemical data about dichloromethane. ... Please find below supplementary chemical data about dichloromethane. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... Nuclear magnetic resonance spectroscopy most commonly known as NMR spectroscopy is the name given to the technique which exploits the magnetic properties of certain nuclei. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or informally, mass-spec and MS) is an analytical technique used to measure the mass-to-charge ratio of ions. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Image File history File links Size of this preview: 800 × 558 pixelsFull resolution (3500 × 2441 pixel, file size: 379 KB, MIME type: image/png) Dichloromethane near IR spectrum. ... Image File history File links Size of this preview: 800 × 558 pixelsFull resolution (3500 × 2441 pixel, file size: 379 KB, MIME type: image/png) Dichloromethane near IR spectrum. ... This article is about spectroscopy. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Solvent (disambiguation). ... An organochloride, organochlorine, or chlorocarbon, is an organic compound containing at least one covalently bonded chlorine atom. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ...

Dichloromethane was first prepared in 1840 by the French chemist Henri Victor Regnault, who isolated it from a mixture of chloromethane and chlorine that had been exposed to sunlight. A chemist pours from a round-bottom flask. ... Henri Victor Regnault (July 21, 1810 – January 19, 1878) was a French chemist and physicist best known for his careful measurements of the thermal properties of gases. ... R-phrases , , S-phrases , , Flash point -46 °C Autoignition temperature 625 °C Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Chloromethane, also called Methyl chloride, or simply R-40 or HCC 40, is a chemical compound... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Prism splitting light High Resolution Solar Spectrum Sunlight in the broad sense is the total spectrum of the electromagnetic radiation given off by the Sun. ...

Production

Industrially, dichloromethane is produced by reacting either methyl chloride or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and methyl chloride undergo a series of reactions producing progressively more chlorinated products. For other uses, see Chemical reaction (disambiguation). ...

CH₄ + Cl₂ → CH₃Cl + HCl

CH₃Cl + Cl₂ → CH₂Cl₂ + HCl

CH₂Cl₂ + Cl₂ → CHCl₃ + HCl

CHCl₃ + Cl₂ → CCl₄ + HCl

The output of these processes is a mixture of methyl chloride, dichloromethane, chloroform, and carbon tetrachloride. These compounds are separated by distillation. Methane is a chemical compound with the molecular formula CH4. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Chloromethane or Methyl chloride is a chemical compound once widely used as a refrigerant. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... R-phrases , , , , S-phrases , , , , , Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ... Chloromethane or Methyl chloride is a chemical compound once widely used as a refrigerant. ... R-phrases , , , S-phrases , Flash point Non-flammable U.S. Permissible exposure limit (PEL) 50 ppm (240 mg/m3) (OSHA) Supplementary data page Structure and properties n, εr, etc. ... R-phrases , , , , S-phrases , , , , , Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ... יחכיטכיגיגיוגקאטגקעיגקDistillation is a method of separating chemical substances based on differences in their volatilities in a boiling liquid mixture. ...

Uses

Dichloromethane's volatility and ability to dissolve a wide range of organic compounds makes it an ideal solvent for many chemical processes. It is widely used as a paint stripper and a degreaser. In the food industry, it was previously used to decaffeinate coffee and to prepare extracts of hops and other flavorings, but most companies no longer use it.^[1]. It is used to chemically weld certain plastics (for example, it is used to seal the casing of electric meters). Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams. It is also used as a fumigant pesticide for stored strawberries and grains. It is also the most common "active" component in Drinking Birds. Concerns about its health effects have led to a search for alternatives in many of these applications. Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to removed paint and clean the underlying surface. ... The food industry is the complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population. ... Caffeine is a xanthine alkaloid compound that acts as a stimulant in humans. ... For the several U.S. counties named Coffee, see Coffee County. ... Hop umbel (branched floral structure resembling nested-inverted umbrellas) in a Hallertau hop yard Hops are a flower used primarily as a flavouring and stability agent in beer, as well as in herbal medicine. ... Flavouring (or flavoring) is a product which is added to food in order to change or augment its taste. ... Aerosol spray can Aerosol spray is a type of canister that sprays an aerosol when its button is pressed or held down. ... A foaming agent is a material that will decompose to release a gas under certain conditions (typically high temperature), which can be used to turn a liquid into a foam. ... A polyurethane is any polymer consisting of a chain of organic units joined by urethane links. ... Sea foam on the beach Foam on a cappuccino Fire-retardant, foamed plastic being used as a temporary dam for firestop mortar in a cable penetration in a pulp and paper mill on Vancouver Island, British Columbia, Canada. ... Fumigation is a method of pest control that completely fills an area with gaseous pesticides to suffocate or poison the pests within. ... A cropduster spreading pesticide. ... For other uses, see Strawberry (disambiguation). ... This article is about cereals in general. ... Drawing of two Drinking Birds. ...

It is used in Christmas lights called bubble lights, in a sealed vial which bubbles when the incandescent light bulb below it is lit. Wurlitzer also used it in their 1940's "bubbler" style jukeboxes. The bubble tubes were up to 30 inches long and used resistors to provide the heat to boil the liquid in a small constricted chamber that had bits of rock and a special glass valve to concentrate the small bubbles into larger ones. It is still used today in their reproduction machines. Dichloromethane is quite often used as a farming tool in Eastern and Central America as a gene adaptation tool.^{[citation needed]} Christmas lights (also sometimes called fairy lights, twinkle lights or holiday lights in the United States) are strands of electric lights used to decorate homes, public/commercial buildings and Christmas trees during the Christmas season. ... A Christmas bubble light, as depicted in a patent illustration. ... Pharmaceutical ampoule, a type of vial. ... Look up bubble in Wiktionary, the free dictionary. ... Incandescence is the release of electromagnetic radiation from a hot body due to its high temperature. ... The light bulb is one of the most significant inventions in the history of the human race, illuminating the darkness of the evening and bringing light indoors at all times in order focus on the task at hand. ... The Rudolph Wurlitzer Company, usually referred to simply as Wurlitzer, is an American company, formerly a producer of stringed instruments, woodwind, brass instruments, theatre organs, band organs, orchestrions, electric pianos and jukeboxes. ... A Zodiac jukebox A jukebox is a partially automated music-playing device, usually a coin-operated machine, that can play specially selected songs from self-contained media. ...

Often sold under the brand name of "EMA Plastic Weld" it is also used extensively in the modelmaking industry for joining plastic components together - it is commonly referred to as "Di-clo".

Toxicity

Dichloromethane is the least toxic of the simple chlorohydrocarbons, but it is not without its health risks as its high volatility makes it an acute inhalation hazard. Dichloromethane is also metabolised by the body to carbon monoxide potentially leading to carbon monoxide poisoning.^[2] Prolonged skin contact can result in the dichloromethane dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns.^[3] Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ... The ability of a liquid to evaporate quickly and at relatively low temperatures. ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ... Carbon monoxide poisoning occurs after the inhalation of carbon monoxide gas. ...

It may be carcinogenic, as it has been linked to cancer of the lungs, liver, and pancreas in laboratory animals.^[4] Dichloromethane crosses the placenta. Fetal toxicity in women who are exposed to it during pregnancy however has not been proven.^[5] In animal experiments it was fetotoxic at doses that were maternally toxic but no teratogenic effects were seen.^[4] The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... The heart and lungs (from an older edition of Grays Anatomy) The lung is an organ belonging to the respiratory system and interfacing to the circulatory system of air-breathing vertebrates. ... The liver is an organ present in vertebrates and some other animals. ... The pancreas is a gland organ in the digestive and endocrine systems of vertebrates[2]. It is both exocrine (secreting pancreatic juice containing digestive enzymes) and endocrine (producing several important hormones, including insulin, glucagon, and somatostatin). ... Fetus at eight weeks A fetus (alternatively foetus or fœtus) is an embryo in later stages of development, from the third month of pregnancy until birth in humans. ... This article is about human pregnancy in biological females. ... Teratology (from the Greek teras (genitive teratos), meaning monster, and logos meaning study) is the medical study of teratogenesis or grossly deformed individuals. ...

In many countries products containing dichloromethane must carry labels warning of its health risks.

See also

• Haloalkane
• Halomethane

Tetrafluoroethane (a haloalkane) is a clear liquid which boils well below room temperature (as seen here) and can be extracted from common canned air canisters by simply inverting them during use. ... Halomethane compounds are molecules of methane (CH4) with one or more of the hydrogen atoms replaced with halogen atoms. ...

References

The California Environmental Protection Agency (Cal/EPA) was created in 1991 by Governor Pete Wilson, through an executive order. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 253rd day of the year (254th in leap years) in the Gregorian calendar. ...

External links

• International Chemical Safety Card 0058
• NIOSH Pocket Guide to Chemical Hazards 0414
• National Pollutant Inventory - Dichloromethane Fact Sheet
• MSDS at Oxford University
• Dichloromethane at National Toxicology Program
• IARC Summaries & Evaluations Vol. 71 (1999)