Editing Chloroform (section)

{{Short description|CHCl3, historical anaesthetic and common solvent}}{{other uses}}{{Use dmy dates|date=April 2023}}
{{Expand Turkish|Kloroform|date=September 2024|fa=yes}}
{{Chembox
|Verifiedimages = changed
|Watchedfields = changed
|verifiedrevid = 407464807
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageFileL1 = Chloroform_displayed.svg
|ImageClassL1 = skin-invert
|ImageFileR1 = Chloroform-3D-balls.png
|ImageFile2 = Chloroform_by_Danny_S._-_002.JPG
|ImageName2 = Chloroform in its liquid state shown in a test tube
|ImageSize2 = 100px
|PIN = Trichloromethane
|OtherNames = {{ubl|''Chloroformium''|Freon 20|Methane trichloride|Methyl trichloride|Methenyl trichloride|Methenyl chloride|Refrigerant-20|terchloride/perchloride of formyle<ref>Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177</ref><ref>Daniel Pereira Gardner, Medicinal Chemistry for the Use of Students and the Profession: Being a Manual of the Science, with Its Applications to Toxicology, Physiology, Therapeutics, Hygiene, Etc (1848), page 271</ref> ''(archaic)''|''Trichloretum Formylicum'' ([[Latin]])}}
|Section1 = {{Chembox Identifiers
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 7V31YC746X
| Abbreviations = R-20, TCM
|InChIKey = HEDRZPFGACZZDS-UHFFFAOYAG
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 44618
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/CHCl3/c2-1(3)4/h1H
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = HEDRZPFGACZZDS-UHFFFAOYSA-N
|CASNo = 67-66-3
|CASNo_Ref = {{cascite|correct|CAS}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 5977
|EINECS = 200-663-8
|PubChem = 6212
| UNNumber =  1888
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 35255
|KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG = C13827
|SMILES = ClC(Cl)Cl
|InChI = 1/CHCl3/c2-1(3)4/h1H
|RTECS = FS9100000
}}
|Section2 = {{Chembox Properties
|C=1|H=1|Cl=3
|Appearance = Highly refractive colorless liquid
|Odor = Sweet, minty, pleasant
|Density = 1.564 g/cm<sup>3</sup> (−20&nbsp;°C)<br /> 1.489 g/cm<sup>3</sup> (25&nbsp;°C)<br /> 1.394 g/cm<sup>3</sup> (60&nbsp;°C)
|MeltingPtC = −63.5
|BoilingPtC = 61.15
|BoilingPt_notes = <br /> decomposes at 450&nbsp;°C
|VaporPressure = 0.62 kPa (−40&nbsp;°C)<br /> 7.89 kPa (0&nbsp;°C)<br /> 25.9 kPa (25&nbsp;°C)<br /> 313 kPa (100&nbsp;°C)<br /> 2.26 MPa (200&nbsp;°C)
|Solubility = 10.62 g/L (0&nbsp;°C)<br /> 8.09 g/L (20&nbsp;°C)<br /> 7.32 g/L (60&nbsp;°C)
|SolubleOther = Soluble in [[benzene]]<br /> Miscible in [[diethyl ether]], [[oil]]s, [[ligroin]], [[ethanol|alcohol]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[carbon disulfide|CS<sub>2</sub>]]
|Solubility1 = ≥ 100 g/L (19&nbsp;°C)
|Solvent1 = acetone
|Solubility2 = ≥ 100 g/L (19&nbsp;°C)
|Solvent2 = dimethyl sulfoxide
|RefractIndex = 1.4459 (20&nbsp;°C)
|LambdaMax = 250 nm, 260 nm, 280 nm
|Viscosity = 0.563 cP (20&nbsp;°C)
|pKa = 15.7 (20&nbsp;°C)
|HenryConstant = 3.67 L·atm/mol (24&nbsp;°C)
|ThermalConductivity = 0.13 W/(m·K) (20&nbsp;°C)
|MagSus = −59.30·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3 = {{Chembox Structure
|MolShape = Tetrahedral
|Dipole = 1.15 D
}}
|Section4 = {{Chembox Thermochemistry
|HeatCapacity = 114.25 J/(mol·K)
|Entropy = 202.9 J/(mol·K)
|DeltaHf = −134.3 kJ/mol
|DeltaGf = −71.1 kJ/mol
|DeltaHc = 473.21 kJ/mol
}}
|Section6 = {{Chembox Pharmacology
|ATCCode_prefix = N01
|ATCCode_suffix = AB02
}}
|Section7 = {{Chembox Hazards
|ExternalSDS = [https://www.merckmillipore.com/Web-IE-Site/en_US/-/EUR/ShowDocument-File?ProductSKU=MDA_CHEM-107024&DocumentType=MSD&DocumentId=107024_SDS_GB_EN.PDF&DocumentUID=370414&Language=EN&Country=GB&Origin=PDP&Display=inline]
|Hazards_ref = <ref name= PubChem>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards|title=PubChem: Safety and Hazards – GHS Classification|publisher=National Center for Biotechnology Information, U.S. National Library of Medicine|access-date=17 August 2018|archive-date=17 August 2018|archive-url=https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards|url-status=live}}</ref>
|MainHazards = Decomposes into [[phosgene]] and [[hydrogen chloride]] in presence of heat – likely carcinogenic – [[reproductive toxicity]] – hepatotoxic<ref name=PGCH/><ref name=":1">Toxicity on [https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity <nowiki>PubChem</nowiki>] {{Webarchive|url=https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity |date=17 August 2018 }}</ref>
|GHSPictograms = {{GHS06}} {{GHS08}} {{GHS corrosion}} 
|GHSSignalWord = Danger
|HPhrases = {{H-phrases|302|315|319|331|336|351|361d|372}}
|PPhrases = {{P-phrases|201|202|260|264|270|271|280|281|301+330+331|310|302+352|304+340|311|305+351+338|308+313|314|332+313|337+313|362|403+233|235|405|501}}
|NFPA-H = 2
|NFPA-F = 0
|NFPA-R = 1
|FlashPt = Nonflammable
|PEL = 50 ppm (240 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0127}}</ref>
|IDLH = 500 ppm<ref name=PGCH/>{{cln|reason=What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind!|date=June 2023}}
|REL = Ca ST 2 ppm (9.78 mg/m<sup>3</sup>) [60-minute]<ref name=PGCH/>
|LD50 = 704 mg/kg (mouse, dermal)<ref>{{cite book |title=Sax's Dangerous Properties of Industrial Materials |edition=12th |year=2012 |last=Lewis |first=Richard J. |publisher=Wiley |isbn=978-0-470-62325-1}}</ref>
|LC50 = 47,702 mg/m<sup>3</sup> (rat, 4 hr)<ref>{{cite web|url=https://www.epa.gov/sites/default/files/2016-09/documents/chloroform.pdf |title=Chloroform |date=September 2016 |website=Environmental Protection Agency |access-date=19 February 2024}}</ref>
|LCLo = {{ubl|20,000 ppm (guinea pig, 2 hr)|7,056 ppm (cat, 4 hr)|25,000 ppm (human, 5 min)}}<ref name=IDLH>{{IDLH|67663|Chloroform}}</ref>{{cln|reason=What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind!|date=June 2023}}
}}
|Section9 = {{Chembox Related
|OtherFunction_label = chloromethanes
|OtherCompounds = {{ubl|[[Deuterated chloroform]] {{chem2|CDCl3}}|[[Chloromethane]] {{chem2|CH3Cl}}|[[Dichloromethane]] {{chem2|CH2Cl2}}|[[Tetrachloromethane]] {{chem2|CCl4}}|[[Fluoroform]] {{chem2|CHF3}}|[[Bromoform]] {{chem2|CHBr3}}|[[Iodoform]] {{chem2|CHI3}}|[[Chlorodifluoromethane]] {{chem2|CHF2Cl}}|[[Dichlorofluoromethane]] {{chem2|CHFCl2}}|[[Bromodichloromethane]] {{chem2|CHCl2Br}}|[[Dibromochloromethane]] {{chem2|CHClBr2}}|[[Bromodifluoromethane]] {{chem2|CHF2Br}}|[[Dibromofluoromethane]] {{chem2|CHFBr2}}}}
}}
}}
'''Chloroform''',<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 661 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The retained names 'bromoform' for HCBr<sub>3</sub>, 'chloroform' for HCCl<sub>3</sub>, and 'iodoform' for HCI<sub>3</sub> are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.| chapter = Front Matter }}</ref> or '''trichloromethane''' (often abbreviated as '''TCM'''), is an [[organochloride]] with the [[chemical formula|formula]] {{chem2|CHCl3|auto=1}} and a common [[solvent]]. It is a [[Volatility (chemistry)|volatile]], colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to [[refrigerant]]s and [[PTFE]].<ref name="Ullmann"> {{Ullmann|last=Rossberg|first=M.|display-authors=etal|title=Chlorinated Hydrocarbons|doi=10.1002/14356007.a06_233.pub2}}</ref> Chloroform was once used as an [[inhalational anesthetic]] between the 19th century and the first half of the 20th century.<ref>{{cite web |url=http://www.history.com/topics/ether-and-chloroform |title=Ether and Chloroform |access-date=2018-04-24 |url-status=live |archive-url=https://web.archive.org/web/20180324191303/https://www.history.com/topics/ether-and-chloroform |archive-date=24 March 2018}}</ref><ref>{{Cite book | doi=10.1002/3527600418.mb6766e0014|chapter = Chloroform [MAK Value Documentation, 2000] |title = The MAK-Collection for Occupational Health and Safety = 20–58|year = 2012|isbn = 978-3-527-60041-0}}</ref> It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C).