Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with formula CHCl₃. It does not undergo combustion in air, although it will burn when mixed with more flammable substances. It is a member of a group of compounds known as trihalomethanes. Chloroform has myriad uses as a reagent and a solvent. It is also considered an environmental hazard. 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). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from... The Permissible Exposure Limit (PEL or OSHA PEL) is a legal limit in the United States for personal exposure to a substance, usually expressed in parts per million (ppm). ... This page provides supplementary chemical data on chloroform. ... This page provides supplementary chemical data on chloroform. ... 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. ... This page provides supplementary chemical data on chloroform. ... This page provides supplementary chemical data on chloroform. ... 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. ... It has been suggested that NMR Data Processing be merged into this article or section. ... 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. ... A Series of Sneaks was the second album by the band Spoon. ... A chemical compound is a chemical substance of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... This article or section does not cite any references or sources. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... A combustion reaction taking place in a igniting match Combustion or burning is a complex sequence of exothermic chemical reactions between a fuel and an oxidant accompanied by the production of heat or both heat and light in the form of either a glow or flames. ... Trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. ... A reagent or reactant is any substance used in a chemical reaction. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ...

History

In 1847, the Edinburgh obstetrician James Young Simpson first used chloroform for general anesthesia during childbirth. The use of chloroform during surgery expanded rapidly thereafter in Europe. In the United States, chloroform began to replace ether as an anesthetic at the beginning of the 20th century; however, it was quickly abandoned in favor of ether upon discovery of its toxicity, especially its tendency to cause fatal cardiac arrhythmia analogous to what is now termed "sudden sniffer's death". Ether is still the preferred anesthetic in some developing nations due to its high therapeutic index and low price. Trichloroethylene, a halogenated aliphatic hydrocarbon related to chloroform, was proposed as a safer alternative, though it too was later found to be carcinogenic. For other uses, see Edinburgh (disambiguation). ... Obstetrics (from the Latin obstare, to stand by) is the surgical specialty dealing with the care of a woman and her offspring during pregnancy, childbirth and the puerperium (the period shortly after birth). ... Sir James Young Simpson, (June 7, 1811–May 6, 1870), professor of midwifery at the University of Edinburgh and physician to Queen Victoria, was a pioneer in Victorian medicine. ... Anesthesia or anaesthesia (see spelling differences) has traditionally meant the condition of having the perception of pain and other sensations blocked. ... Parturition redirects here. ... “Surgeon” redirects here. ... This article is about the chemical compound. ... Cardiac arrhythmia is any of a group of conditions in which the electrical activity of the heart is irregular or is faster or slower than normal. ... Volatile substance abuse or solvent abuse (called huffing) is the practice of inhaling volatile substances for their psychoactive effects. ... This article is about the chemical compound. ... A developing country is a country with low average income compared to the world average. ... The therapeutic index of a medication is a comparison of the amount that causes the therapeutic effect to the amount that causes toxic effects. ... The chemical compound trichloroethylene is a chlorinated hydrocarbon commonly used as an industrial solvent. ... An alkane in organic chemistry is a type of hydrocarbon in which the molecule has the maximum possible number of hydrogen atoms and so has no double bonds (they are saturated). ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ...

Production

Industrially, chloroform is produced by heating a mixture of chlorine and either chloromethane or methane. At 400-500 °C, a free radical halogenation occurs, converting the methane or chloromethane to progressively more chlorinated compounds. 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. ... Methane is a chemical compound with the molecular formula CH4. ... This reaction is typical of alkanes and alkyl-substituted aromatics. ... Methane is a chemical compound with the molecular formula CH4. ... Chloromethane or Methyl chloride is a chemical compound once widely used as a refrigerant. ...

CH₄ + Cl₂ → CH₃Cl + HCl

CH₃Cl + Cl₂ → CH₂Cl₂ + HCl

CH₂Cl₂ + Cl₂ → CHCl₃ + HCl

Chloroform undergoes further chlorination to give CCl₄: R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... R-phrases , , , , S-phrases , , , , , Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ...

CHCl₃ + Cl₂ → CCl₄ + HCl

The output of this process is a mixture of the four chloromethanes: chloromethane, dichloromethane, chloroform (trichloromethane), and carbon tetrachloride, which are then separated by distillation. יחכיטכיגיגיוגקאטגקעיגקDistillation is a method of separating chemical substances based on differences in their volatilities in a boiling liquid mixture. ...

Chloroform was first produced industrially by the reaction of acetone (or ethanol) with sodium hypochlorite or calcium hypochlorite, known as the haloform reaction. The chloroform can be removed from the attendant acetate salts (or formate salts if ethanol is the starting material) by distillation. This reaction is still used for the production of bromoform and iodoform. The haloform process is obsolete for the production of ordinary chloroform. It is, however, used to produce deuterated material industrially. Deuterochloroform is prepared by the reaction of sodium deuteroxide with chloral hydrate. ALL of the aldehyde hydrogen is retained in the product, though, and samples of higher isotopic purity are obtained from trichloroacetophenone as starting material.^{[citation needed]} The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages. ... Sodium hypochlorite is a chemical compound with the formula NaClO. A solution of sodium hypochlorite is frequently used as a disinfectant and as a bleaching agent; indeed, often it is simply called bleach, though other chemicals are sometimes given that name as well. ... Calcium hypochlorite is a chemical compound with formula Ca(ClO)2. ... The haloform reaction is a chemical reaction where a haloform (CHX3) is produced by the multiple halogenation of a methyl ketone (a molecule containing the R-CO-CH3 group) in the presence of a base [1] . R may be H, alkyl or aryl. ... An acetate, or ethanoate, is a salt or ester of acetic acid. ... Formate or methanoate is the ion is HCOO- (formic acid minus one hydrogen ion). ... R-phrases , , , , S-phrases , , U.S. Permissible exposure limit (PEL) 0. ... The compound iodoform is a yellow, crystalline, volatile substance, I3CH, having a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and sweetish taste, and analogous to chloroform. ... Chloral hydrate, also known as trichloroacetaldehyde monohydrate, 2,2,2-trichloro-1,1-ethanediol, and under the tradenames Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, and Somnote, is a sedative and hypnotic drug as well as a chemical reagent and precursor. ...

Inadvertent synthesis of chloroform

Haloform-like reactions also occur inadvertently even in domestic settings. Sodium hypochlorite solution (chlorine bleach) and methyl ethyl ketone (nail-varnish remover) produces chloroform. Commercial chlorine bleach To bleach something is to remove or lighten its colour, sometimes as a preliminary step in the process of dyeing; a bleach is a chemical that produces these effects, often via oxidation. ... 2-Butanone is a manufactured organic chemical but it is also present in the environment from natural sources. ...

Pool chlorine and acetone will also produce chloroform. General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ...

Uses

The major use of chloroform today is in the production of the freon refrigerant R-22. However, as the Montreal Protocol takes effect, this use can be expected to decline as R-22 is replaced by refrigerants that are less liable to result in ozone depletion. In addition, it is used under research conditions to anesthetize mosquitoes for experiments, most frequently for the study of malaria. Freon is a trade name for a group of chlorofluorocarbons used primarily as a refrigerant. ... The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide. ... The largest Antarctic ozone hole recorded as of September 2000 For other similarly-named agreements, see Montreal Protocol (disambiguation). ... Global monthly average total ozone amount Ozone depletion describes two distinct, but related observations: a slow, steady decline of about 4 percent per decade in the total amount of ozone in Earths stratosphere since around 1980; and a much larger, but seasonal, decrease in stratospheric ozone over Earths...

As a solvent

Chloroform is a common solvent because it is relatively unreactive, miscible with most organic liquids, and conveniently volatile. Small amounts of chloroform are used as a solvent in the pharmaceutical industry and for producing dyes and pesticides. Chloroform is an effective solvent for alkaloids in their base form and thus plant material is commonly extracted with chloroform for pharmaceutical processing. For example, it is commercially used to extract morphine from poppies, scopolamine from Datura plants. Chloroform containing deuterium (heavy hydrogen), CDCl₃, is a common solvent used in NMR spectroscopy. It can be used to bond pieces of acrylic glass (which is also known under the trade name 'Perspex'). A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Pharmacology (in Greek: pharmacon is drug, and logos is science) is the study of how chemical substances interfere with living systems. ... Look up dye in Wiktionary, the free dictionary. ... A cropduster spreading pesticide. ... Morphine (INN) (IPA: ) is a highly potent opiate analgesic drug and is the principal active agent in opium and the prototypical opiate. ... A wild field of poppies, West Azarbaijan Province, Iran A poppy is any of a number of showy flowers, born one per stem, belonging to the poppy family. ... Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). ... Species See text below Datura is a genus of 12-15 species of vespertine flowering plants belonging to the family Solanaceae. ... Deuterium, also called heavy hydrogen, is a stable isotope of hydrogen with a natural abundance in the oceans of Earth of approximately one atom in 6500 of hydrogen (~154 PPM). ... ... It has been suggested that NMR Data Processing be merged into this article or section. ... Structure of methyl methacrylate, the monomer that makes up PMMA Polymethyl methacrylate (PMMA) or poly(methyl 2-methylpropenoate) is the synthetic polymer of methyl methacrylate. ...

As a reagent in organic synthesis

As a reagent, chloroform serves as a source of the dichlorocarbene CCl₂ group.^[1] It reacts with aqueous sodium hydroxide (usually in the presence of a phase transfer catalyst) to produce dichlorocarbene, CCl₂.^[2][3] This reagent effects ortho-formylation of activated aromatic rings such as phenols, producing aryl aldehydes in a reaction known as the Reimer-Tiemann reaction. Alternatively the carbene can be trapped by an alkene to form a cyclopropane derivative. Sodium hydroxide (NaOH), also known as lye or caustic soda or sodium hydrate, is a caustic metallic base. ... A phase transfer catalyst or PTC in chemistry is a type of chemical compound, often a quaternary ammonium salt, which facilitates the migration of a particular chemical component in one phase into a other phase in a heterogeneous system. ... In chemistry a carbene is a short-lived and highly reactive organic molecule with a divalent carbon atom with only 6 valence electrons and the general formula: R1R2C:. The carbon atom is sp2 hybridised with a empty p-orbital extending above and below a plane containing R1 and R2 and... In chemistry, an aromatic molecule is one in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... An aldehyde. ... The Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols. ... In chemistry a carbene is a short-lived and highly reactive organic molecule with a divalent carbon atom with only six valence electrons and the general formula: R1R2C: . The carbon atom is sp2 hybridised with an empty p-orbital extending above and below a plane containing R1 and R2 and... The chemical structure of ethylene, the simplest alkene. ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ...

Safety

As might be expected from its use as an anesthetic, inhaling chloroform vapors depresses the central nervous system. IDLH according to NIOSH is approximately 500 ppm. Breathing about 900 parts of chloroform per million parts air (900 parts per million) for a short time can cause dizziness, fatigue, and headache. Chronic chloroform exposure may cause damage to the liver (where chloroform is metabolized to phosgene) and to the kidneys, and some people develop sores when the skin is immersed in chloroform. A general anaesthetic drug is an anaesthetic (or anesthetic AE) drug that brings about a reversible loss of consciousness. ... A diagram showing the CNS: 1. ... Immediately Dangerous to Life and Health (IDLH or NIOSH IDLH) is a limit for personal exposure to a substance defined by the United States National Institute for Occupational Safety and Health (NIOSH), normally expressed in parts per million (ppm). ... The National Institute for Occupational Safety and Health (NIOSH) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ... Phosgene is a highly toxic chemical compound with the formula COCl2. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ...

Animal studies have shown that miscarriages occur in rats and mice that have breathed air containing 30 to 300 ppm chloroform during pregnancy and also in rats that have ingested chloroform during pregnancy. Offspring of rats and mice that breathed chloroform during pregnancy have a higher incidence of birth defects, and abnormal sperm have been found in male mice that have breathed air containing 400 ppm chloroform for a few days. The effect of chloroform on reproduction in humans is unknown. Miscarriage or spontaneous abortion is the natural or accidental termination of a pregnancy at a stage where the embryo or the fetus is incapable of surviving, generally defined at a gestation of prior to 20 weeks. ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ... A pregnant woman near the end of her term Pregnancy is the carrying of one or more offspring in an embryonal or fetal stage of development by female mammals, including humans, inside their bodies, between the stages of conception and birth. ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ... A spermatozoon or spermatozoan ( spermatozoa), from the ancient Greek σπέρμα (seed) and (living being) and more commonly known as a sperm cell, is the haploid cell that is the male gamete. ... For other uses, see Reproduction (disambiguation) Reproduction is the biological process by which new individual organisms are produced. ...

Chloroform once appeared in toothpastes, cough syrups, ointments, and other pharmaceuticals, but it has been banned in consumer products in the United States since 1976.

The NTP's eleventh report on carcinogens implicates it as reasonably anticipated to be a human carcinogen, a designation equivalent to IARC class 2A. It has been most readily associated with hepatocellular carcinoma. Caution is mandated during its handling in order to minimize unnecessary exposure; safer alternatives, such as dichloromethane, have resulted in a substantial reduction of its use as a solvent. The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... Hepatocellular carcinoma (HCC, also called hepatoma) is a primary malignancy (cancer) of the liver. ... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ...

During prolonged storage hazardous amounts of phosgene can accumulate in the presence of oxygen and ultraviolet light. To prevent accidents commercial material is stabilized with ethanol or amylene, but samples that have been recovered or dried no longer contain any stabilizer and caution must be taken with those. Suspicious bottles should be tested for phosgene. Filter paper strips, wetted with 5% diphenylamine, 5% dimethylaminobenzaldehyde, and then dried, turn yellow in phosgene vapor. Phosgene is a highly toxic chemical compound with the formula COCl2. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... “UV” redirects here. ... Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound, and is best known as the alcohol found in alcoholic beverages. ... Pentene is a hydrocarbon with chemical formula C5H10 containing a single double bond within its molecular structure. ...

Commonly used in DNA extractions and generally in conjunction with phenol to form a biolayer with extraction buffer (tris etc). DNA will form in the supernatant while protein and non soluble cell materials will precipitate between the buffer chloroform layers.

In popular culture

See chloroform's entries at fictional applications of real materials.

• Wonder Woman - Season 1 - "Fausta, the Nazi Wonder Woman": Wonder Woman falls through a trap door and is chloroformed in to a semi conscious state while she is questioned. After the assailant gets the information he needs from her, she is knocked out completely with chloroform.
• C.J. Parker (Pamela Anderson) Baywatch - Season 3 - "Dead of Summer": C.J. moves on to the personal watercraft of two men to assist a man who has supposedly suffered a heart attack. The man pulls a gun on her while the other man grabs her from behind. C.J. has her hands bound to the steering wheel. She is then chloroformed by the man.
• Caroline Parker (Yasmine Bleeth) Baywatch Nights - Caroline goes in to the locker room wearing her Baywatch swim suit. She sees a box of kittens and starts to look at them. A man sneaks up behind her and chloroforms her in to unconciousness.
• Buffy the Vampire Slayer - Season 7 - Xander uses chloroform to knock out Dawn, in order to take her away from Sunnydale.
• Chloroform is used many times in Herge's Tintin

In various fictional settings, real materials may be portrayed as having different or additional properties, particularly when interacting with the unique elements of the setting itself. ... The main characters and others from The Castafiore Emerald, one of the later books The Adventures of Tintin (French: ) is a series of Belgian comic books created by Belgian artist Hergé, the pen name of Georges Remi (1907–1983). ...

References

1. ^ Srebnik, M.; Laloë, E. "Chloroform" Encyclopedia of Reagents for Organic Synthesis" 2001 John Wiley. DOI: 10.1002/047084289X.rc105
2. ^ Vogel, E.; Klug, W.; Breuer. A. "1,6-Methano[10]annulne" Organic Syntheses, Collected Volume 6, p.731 (1988). CV6P0731.pdf
3. ^ Gokel, G. W.; Widera, R. P.; Weber, W. P. Phase-Transfer Hofmann Carbylamine Reaction: tert-Butyl Isocyanide" Organic Syntheses, Collected Volume 6, p.232 (1988).

See also

• Haloalkane
• Halomethane
• Chloromethane
• Dichloromethane
• Carbon tetrachloride (Tetrachloromethane)
• Fluoroform
• Bromoform
• Iodoform

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. ... 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... Dichloromethane or Methylene chloride is a chemical compound widely used as a solvent for organic materials. ... R-phrases , , , , S-phrases , , , , , Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ... Fluoroform CHF3; CAS number, also known as trifluoromethane, is one of the haloalkanes with zero ozone depletion, as it does not contain any chlorine. ... R-phrases , , , , S-phrases , , U.S. Permissible exposure limit (PEL) 0. ... The compound iodoform is a yellow, crystalline, volatile substance, I3CH, having a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and sweetish taste, and analogous to chloroform. ...

External links

• Chloroform "The Molecular Lifesaver" An article at Oxford University providing interesting facts about chloroform.
• Concise International Chemical Assessment Document 58
• History of chloroform anesthesia
• IARC Summaries & Evaluations: Vol. 1 (1972), Vol. 20 (1979), Suppl. 7 (1987), Vol. 73 (1999)
• International Chemical Safety Card 0027
• NIOSH Pocket Guide to Chemical Hazards 0127
• National Pollutant Inventory - Chloroform and trichloromethane
• NIST Standard Reference Database
• Story on Chloroform from BBC's The Material World (28 July 2005)
• Sudden Sniffer's Death Syndrome article at Carolina Poison Center