Bromodichloromethane

{{chembox | Watchedfields = changed | verifiedrevid = 443428002 | ImageCaption = Chemical diagram | ImageFile_Ref = {{chemboximage|correct|??}} | ImageCaption1 = Spacefill model | ImageFile = Bromodichloromethane displayed.svg | ImageFile1 = Bromodichloromethane pubchem spacefill model.png | ImageSize = | PIN = Bromo(dichloro)methane  | OtherNames = Bromodichloromethane Dichlorobromomethane | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 6119 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C14708 | InChIKey = FMWLUWPQPKEARP-UHFFFAOYAR | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 346231 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/CHBrCl2/c2-1(3)4/h1H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FMWLUWPQPKEARP-UHFFFAOYSA-N | CASNo = 75-27-4 | CASNo_Ref = {{cascite|correct|CAS}} | EINECS = 200-856-7 | RTECS = PA5310000 | PubChem = 6359 | Gmelin = 25941 | Beilstein = 1697005 | UNNumber = 2810 3082 | UNII = 7LN464CH2O | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 34591 | SMILES = BrC(Cl)Cl | InChI = 1/CHBrCl2/c2-1(3)4/h1H }} | Section2 = {{Chembox Properties | Formula = CHBrCl2 | MolarMass = 163.8 g/mol | Appearance = Colorless liquid | Density = 1.980 g/cm3 | MeltingPtC = -57 | MeltingPt_notes = | BoilingPtC = 90 | BoilingPt_notes = | RefractIndex = 1.4964 | Solubility = 4.5 g/L at 20 °C | MagSus = −66.3·10−6 cm3/mol }} | Section7 = {{Chembox Hazards | MainHazards = | GHSPictograms = {{GHS07}}{{GHS08}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|302|315|319|335|350}} | PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+340|305+351+338|308+313|312|321|330|332+313|337+313|362|403+233|405|501}} | FlashPt = | AutoignitionPt = }} }}

'''Bromodichloromethane''' is a trihalomethane with formula {{chem2|CHBrCl2|auto=1}}. It is a colorless, nonflammable liquid which will dissolve in water, or evaporate in air.<ref name=":0">{{Cite web |title=ToxFAQs™: Bromodichloromethane |url=https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsDetails.aspx?faqid=707&toxid=127 |access-date=2024-08-13 |website=Agency for Toxic Substances and Disease Registry |publisher=CDC}}</ref> Most of the chemical is produced through the chlorine disinfection process,<ref name=":0" /> and as a result it can occur in municipally-treated drinking water.<ref>Agency for Toxic Substances & Disease Registry, Accessed 07/10/2012, https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=707&tid=127</ref> It is also produced in small quantities by oceanic algae.<ref name=":0" /> According to the CDC, levels normal in drinking water are not known to cause health problems, but it has been classified by the US EPA as a probable human carcinogen.

Bromodichloromethane has formerly been used as a flame retardant, and a solvent for fats and waxes and for mineral ore separation. Now it is only used as a reagent or intermediate in organic chemistry.<ref>{{Cite web |date=2004 |title=Trihalomethanes in Drinking-water |url=https://www.who.int/docs/default-source/wash-documents/wash-chemicals/trihalomethanes.pdf?sfvrsn=3d3a90e3_4 |access-date=5 September 2025 |website=World Health Organization}}</ref> In the US it is only produced in small quantities, which are used for these chemical reasons.<ref name=":0" /> For example, it can be used to produce phenyl(bromodichloromethyl)mercury, which is widely used in the production of dichlorocarbene.<ref name=":1">{{Cite book |url=https://publications.iarc.fr/Book-And-Report-Series/Iarc-Monographs-On-The-Identification-Of-Carcinogenic-Hazards-To-Humans/Chlorinated-Drinking-water-Chlorination-By-products-Some-Other-Halogenated-Compounds-Cobalt-And-Cobalt-Compounds-1991 |title=Chlorinated Drinking-water; Chlorination By-products; Some Other Halogenated Compounds; Cobalt and Cobalt Compounds: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans Volume 52 |year=1991 |isbn=978-92-832-1252-2 |volume=52 |pages=179–212 |language=en}}</ref> It can be prepared by treating a mixture of chloroform and bromoform with triethyl-benzylammonium chloride and sodium hydroxide.<ref name=":1" />

== Toxicity == According to the CDC, {{As of|2020|lc=y}}, levels that it is normal to be exposed to in drinking water are lower than levels known to cause health problems.<ref name=":0" /> A small number of studies have examined the effects of low levels of bromodichloromethane on people, but most were also exposed to other chemicals, so it may not be the only cause of reported health problems.<ref name=":0" /> Studies in animals with much higher levels of the chemical than what humans are normally exposed to have resulted in health problems.<ref name=":0" /> The effects of the chemical on children are unknown but expected to be the same as on adults.<ref name=":0" />

{{As of|2020}}, the chemical (in sufficient quantities) is considered by the US Department of Health and Human Services to be reasonably anticipated to be a human carcinogen, and by the U.S. Environmental Protection Agency (EPA) to be a probable human carcinogen.<ref name=":0" /> No standards regulating its presence in drinking water currently exist in the United States, though a limit of 80 ppb exists for the total amount of trihalomethanes in general.<ref>{{Cite web |last= |first= |date=2015-11-30 |title=National Primary Drinking Water Regulations |url=https://www.epa.gov/ground-water-and-drinking-water/national-primary-drinking-water-regulations |access-date=2025-09-05 |website=Environmental Protection Agency |language=en}}</ref>

==Notes== {{reflist}}

==External links== * {{ICSC|0393|03}} * [http://cpdb.thomas-slone.org/chempages/BROMODICHLOROMETHANE.html Bromodichloromethane at The Carcinogenic Potency Database] * [https://wwwn.cdc.gov/TSP/index.aspx?toxid=127 Toxicological Profile at ATSDR]

Category:Bromochloroalkanes Category:Halomethanes Category:IARC Group 2B carcinogens