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orm 4 2 inadvertent formation of chloroform 5 uses toggle uses subsection 5 1 solvent 5 2 refrigerant 5 3 lewis acid 5 4 reagent 5 5 anaesthetic 5 6 recreational use 5 7 criminal use 6 safety toggle safety subsection 6 1 exposure 6 2 pharmacology 6 3 conversion to phosgene 6 4 regulation 7 bioremediation of chloroform 8 gallery 9 references 10 external links toggle the table of contents chloroform 67 languages afrikaans العربية azərbaycanca تۆرکجه беларуская тарашкевіца беларуская български ပအိုဝ်ႏဘာႏသာႏ বাংলা bosanski català čeština dansk deutsch ελληνικά esperanto español eesti euskara فارسی suomi français gaeilge galego עברית हिन्दी hrvatski magyar հայերեն bahasa indonesia ido italiano 日本語 қазақша 한국어 kurdî кыргызча lëtzebuergesch lietuvių latviešu македонски bahasa melayu မြန်မာဘာသာ nederlands norsk bokmål polski português ရခိုင် română русский srpskohrvatski српскохрватски simple english slovenčina slovenščina shqip српски srpski svenska தமிழ் తెలుగు ไทย türkçe українська اردو oʻzbekcha ўзбекча tiếng việt 粵語 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chcl3 historical anaesthetic and common solvent for other uses see chloroform disambiguation you can help expand this article with text translated from the corresponding article in turkish september 2024 click show for important translation instructions view a machine translated version of the turkish article machine translation like deepl or google translate is a useful starting point for translations but translators must follow the llm translation guideline revise errors as necessary and confirm that the translation is accurate rather than simply copy pasting machine translated text into the english wikipedia do not translate text that appears unreliable or low quality if possible verify the text with references provided in the foreign language article you must provide copyright attribution in the edit summary accompanying your translation by providing an interlanguage link to the source of your translation a model attribution edit summary is content in this edit is translated from the existing turkish wikipedia article at tr kloroform see its history for attribution you may also add the template translated tr kloroform to the talk page for more guidance see wikipedia translation chloroform chloroform in its liquid state shown in a test tube names preferred iupac name trichloromethane other names chloroformium freon 20 methane trichloride methyl trichloride methenyl trichloride methenyl chloride refrigerant 20 terchloride perchloride of formyle 1 2 archaic trichloretum formylicum latin identifiers cas number 67 66 3 y 3d model jsmol interactive image abbreviations r 20 tcm chebi chebi 35255 y chembl chembl44618 y chemspider 5977 y echa infocard 100 000 603 ec number 200 663 8 kegg c13827 y pubchem cid 6212 rtecs number fs9100000 unii 7v31yc746x y un number 1888 comptox dashboard epa dtxsid1020306 inchi inchi 1s chcl3 c2 1 3 4 h1h y key hedrzpfgaczzds uhfffaoysa n y inchi 1 chcl3 c2 1 3 4 h1h key hedrzpfgaczzds uhfffaoyag smiles clc cl cl properties chemical formula c h cl 3 molar mass 119 37 g mol 1 appearance highly refractive colorless liquid odor sweet minty pleasant density 1 564 g cm 3 20 c 1 489 g cm 3 25 c 1 394 g cm 3 60 c melting point 63 5 c 82 3 f 209 7 k boiling point 61 15 c 142 07 f 334 30 k decomposes at 450 c solubility in water 10 62 g l 0 c 8 09 g l 20 c 7 32 g l 60 c solubility soluble in benzene miscible in diethyl ether oils ligroin alcohol ccl 4 cs 2 solubility in acetone 100 g l 19 c solubility in dimethyl sulfoxide 100 g l 19 c vapor pressure 0 62 kpa 40 c 7 89 kpa 0 c 25 9 kpa 25 c 313 kpa 100 c 2 26 mpa 200 c henry s law constant k h 3 67 l atm mol 24 c acidity p k a 15 7 20 c uv vis λ max 250 nm 260 nm 280 nm magnetic susceptibility χ 59 30 10 6 cm 3 mol thermal conductivity 0 13 w m k 20 c refractive index n d 1 4459 20 c viscosity 0 563 cp 20 c structure molecular shape tetrahedral dipole moment 1 15 d thermochemistry heat capacity c 114 25 j mol k std molar entropy s 298 202 9 j mol k std enthalpy of formation δ f h 298 134 3 kj mol gibbs free energy δ f g 71 1 kj mol std enthalpy of combustion δ c h 298 473 21 kj mol pharmacology atc code n01ab02 who hazards 3 occupational safety and health ohs osh main hazards decomposes into phosgene and hydrogen chloride in presence of heat likely carcinogenic reproductive toxicity hepatotoxic 4 5 ghs labelling pictograms signal word danger hazard statements h302 h315 h319 h331 h336 h351 h361d h372 precautionary statements p201 p202 p235 p260 p264 p270 p271 p280 p281 p301 p330 p331 p302 p352 p304 p340 p305 p351 p338 p308 p313 p310 p311 p314 p332 p313 p337 p313 p362 p403 p233 p405 p501 nfpa 704 fire diamond 2 0 0 flash point nonflammable lethal dose or concentration ld lc ld 50 median dose 704 mg kg mouse dermal 6 lc 50 median concentration 47 702 mg m 3 rat 4 hr 7 lc lo lowest published 20 000 ppm guinea pig 2 hr 7 056 ppm cat 4 hr 25 000 ppm human 5 min 8 niosh us health exposure limits pel permissible 50 ppm 240 mg m 3 4 rel recommended ca st 2 ppm 9 78 mg m 3 60 minute 4 idlh immediate danger 500 ppm 4 safety data sheet sds related compounds related compounds deuterated chloroform cdcl 3 chloromethane ch 3 cl dichloromethane ch 2 cl 2 tetrachloromethane ccl 4 fluoroform chf 3 bromoform chbr 3 iodoform chi 3 chlorodifluoromethane chf 2 cl dichlorofluoromethane chfcl 2 bromodichloromethane chcl 2 br dibromochloromethane chclbr 2 bromodifluoromethane chf 2 br dibromofluoromethane chfbr 2 supplementary data page chloroform data page except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound chloroform 9 or trichloromethane often abbreviated as tcm is an organochloride with the formula c h cl 3 and a common solvent it is a volatile colorless sweet smelling dense liquid produced on a large scale as a precursor to refrigerants and polytetrafluoroethylene ptfe 10 chloroform was once used as an inhalational anesthetic between the 19th century and the first half of the 20th century 11 12 it is miscible with many solvents but it is only very slightly soluble in water only 8 g l at 20 c structure and name edit the molecule adopts a tetrahedral molecular geometry with c 3v symmetry 13 the chloroform molecule can be viewed as a methane molecule with three hydrogen atoms replaced with three chlorine atoms leaving a single hydrogen atom the name chloroform is a portmanteau of terchloride tertiary chloride a trichloride and formyle an obsolete name for the methylylidene radical ch derived from formic acid 14 natural occurrence edit many kinds of seaweed produce chloroform and fungi are believed to produce chloroform in soil 15 abiotic processes are also believed to contribute to natural chloroform productions in soils although the mechanism is still unclear 16 history edit chloroform was synthesized independently by several investigators c 1831 moldenhawer a german pharmacist from frankfurt an der oder appears to have produced chloroform in 1830 by mixing chlorinated lime with ethanol however he mistook it for chloräther chloric ether 1 2 dichloroethane 17 18 samuel guthrie a u s physician from sackets harbor new york also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol and noted its anaesthetic properties however he also believed that he had prepared chloric ether 19 20 21 justus von liebig carried out the alkaline cleavage of chloral liebig incorrectly states that the empirical formula of chloroform was c 2 cl 5 and named it chlorkohlenstoff carbon chloride 22 23 eugène soubeiran obtained the compound by the action of chlorine bleach on both ethanol and acetone 24 in 1834 french chemist jean baptiste dumas determined chloroform s empirical formula and named it 25 es scheint mir also erweisen dass die von mir analysirte substanz zur formel hat c 2 h 2 cl 6 thus it seems to me to show that the substance i analyzed has as its empirical formula c 2 h 2 cl 6 note the coefficients of his empirical formula should be halved diess hat mich veranlasst diese substanz mit dem namen chloroform zu belegen this had caused me to impose the name chloroform upon this substance i e formyl chloride or chloride of formic acid in 1835 dumas prepared the substance by alkaline cleavage of trichloroacetic acid in 1842 robert mortimer glover in london discovered the anaesthetic qualities of chloroform on laboratory animals 26 in 1847 scottish obstetrician james y simpson was the first to demonstrate the anaesthetic properties of chloroform provided by local pharmacist william flockhart of duncan flockhart and company 27 in humans and helped to popularize the drug for use in medicine 28 the application of chloroform remained dangerous and many deaths occurred through accidental overdose 29 30 in 1848 english physician john snow developed an inhaler that regulated the dosage 29 by the 1850s chloroform was being produced on a commercial basis 30 an apparatus that could apply it safely and controllably was invented by english physician joseph thomas clover in 1862 31 32 in britain about 750 000 doses a week were being produced by 1895 30 using the liebig procedure which retained its importance until the 1960s today chloroform along with dichloromethane is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane 10 production edit industrially chloroform is produced by heating a mixture of chlorine and either methyl chloride ch 3 cl or methane ch 4 10 at 400 500 c free radical halogenation occurs converting these precursors to progressively more chlorinated compounds ch 4 cl 2 ch 3 cl hcl ch 3 cl cl 2 ch 2 cl 2 hcl ch 2 cl 2 cl 2 chcl 3 hcl chloroform undergoes further chlorination to yield carbon tetrachloride ccl 4 chcl 3 cl 2 ccl 4 hcl the output of this process is a mixture of the four chloromethanes chloromethane methylene chloride dichloromethane trichloromethane chloroform and tetrachloromethane carbon tetrachloride these can then be separated by distillation 10 chloroform may also be produced on a small scale via the haloform reaction between acetone and sodium hypochlorite 3 naocl ch 3 2 co chcl 3 2 naoh ch 3 coona deuterochloroform edit main article deuterated chloroform deuterated chloroform is an isotopologue of chloroform with a single deuterium atom cdcl 3 is a common solvent used in nmr spectroscopy deuterochloroform is produced by the reaction of hexachloroacetone with heavy water 33 the haloform process is now obsolete for production of ordinary chloroform deuterochloroform can also be prepared by reacting sodium deuteroxide with chloral hydrate 34 35 inadvertent formation of chloroform edit the haloform reaction can also occur inadvertently in domestic settings sodium hypochlorite solution chlorine bleach mixed with common household liquids such as acetone methyl ethyl ketone ethanol or isopropyl alcohol can produce some chloroform in addition to other compounds such as chloroacetone or dichloroacetone 36 37 uses edit in terms of scale the most important reaction of chloroform is with hydrogen fluoride to give monochlorodifluoromethane hcfc 22 a precursor in the production of polytetrafluoroethylene teflon and other fluoropolymers 10 chcl 3 2 hf chclf 2 2 hcl the reaction is conducted in the presence of a catalytic amount of mixed antimony halides chlorodifluoromethane is then converted to tetrafluoroethylene the main precursor of teflon 38 solvent edit the hydrogen attached to carbon in chloroform participates in hydrogen bonding 39 40 making it a good solvent for many materials worldwide chloroform is also used in pesticide formulations as a solvent for lipids rubber alkaloids waxes gutta percha and resins as a cleaning agent as a grain fumigant and in fire extinguishers 41 42 cdcl 3 is a common solvent used in nmr spectroscopy 43 refrigerant edit chloroform is used as a precursor to make r 22 chlorodifluoromethane this is done by reacting it with hydrofluoric acid hf which fluorinates the chcl 3 molecule and releases hydrochloric acid as a byproduct 44 before the montreal protocol was enforced most of the chloroform produced in the united states was used in the production of chlorodifluoromethane however its production remains high as it is a key precursor of ptfe 45 although chloroform has properties such as a low boiling point and a low global warming potential of only 31 compared to the 1760 of r 22 which are appealing properties for a refrigerant there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products 46 lewis acid edit in solvents such as ccl 4 and alkanes chloroform hydrogen bonds to a variety of lewis bases hccl 3 is classified as a hard acid and the ecw model lists its acid parameters as e a 1 56 and c a 0 44 reagent edit as a reagent chloroform serves as a source of the dichlorocarbene intermediate ccl 2 47 it reacts with aqueous sodium hydroxide usually in the presence of a phase transfer catalyst to produce dichlorocarbene ccl 2 48 49 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 in the kharasch addition chloroform forms the chcl 2 free radical which adds to alkenes 50 anaesthetic edit antique bottles of chloroform chloroform is a powerful general anesthetic euphoriant anxiolytic and sedative when inhaled or ingested the anaesthetic qualities of chloroform were first described in 1842 in a thesis by robert mortimer glover which won the gold medal of the harveian society for that year 51 52 glover also undertook practical experiments on dogs to prove and refine his theories and subsequently presented them in his doctoral thesis at the university of edinburgh in the summer of 1847 identifying anaesthetizing halogenous compounds as a new order of poisonous substances 51 james young simpson a scottish obstetrician was one of those examiners required to read the thesis but later claimed to have never read it and to have come to his own conclusions independently 51 perkins mcvey among others have raised doubts about the credibility of simpson s claim noting that simpson s publications on the subject in 1847 explicitly echo glover s and being one of the thesis examiners simpson was likely aware of the content of glover s study even if he skirted his duties as an examiner 51 in 1847 and 1848 glover would p...
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