Bromodichloromethane

Bromodichloromethane
Names
Chemical diagram
Spacefill model
Preferred IUPAC name Bromo(dichloro)methane
Other names Bromodichloromethane Dichlorobromomethane
Identifiers
CAS Number	75-27-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1697005
ChEBI	CHEBI:34591^Y
ChEMBL	ChEMBL346231^Y
ChemSpider	6119^Y
ECHA InfoCard	100.000.779
EC Number	200-856-7
Gmelin Reference	25941
KEGG	C14708^Y
PubChem CID	6359
RTECS number	PA5310000
UNII	7LN464CH2O
UN number	2810 3082
CompTox Dashboard (EPA)	DTXSID1020198
InChI InChI=1S/CHBrCl2/c2-1(3)4/h1H^Y Key: FMWLUWPQPKEARP-UHFFFAOYSA-N^Y InChI=1/CHBrCl2/c2-1(3)4/h1H Key: FMWLUWPQPKEARP-UHFFFAOYAR
SMILES BrC(Cl)Cl
Properties
Chemical formula	CHBrCl₂
Molar mass	163.8 g/mol
Appearance	Colorless liquid
Density	1.980 g/cm³
Melting point	−57 °C (−71 °F; 216 K)
Boiling point	90 °C (194 °F; 363 K)
Solubility in water	4.5 g/L at 20 °C
Magnetic susceptibility (χ)	-66.3·10⁻⁶ cm³/mol
Refractive index (n_D)	1.4964
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H315, H319, H335, H350
Precautionary statements	P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Bromodichloromethane is a trihalomethane with formula C H Br Cl₂. It is a colorless, nonflammable liquid which will dissolve in water, or evaporate in air.^[1] Most of the chemical is produced through the chlorine disinfection process,^[1] and as a result it can occur in municipally-treated drinking water.^[2] It is also produced in small quantities by algae in the oceans.^[1] 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 because of its high density for mineral separation.^{[citation needed]} Now it is only used as a reagent or intermediate in organic chemistry.^{[citation needed]} In the US it is only produced in small quantities, which are used for these chemical reasons.^[1] For example, it can be used to produce phenyl(bromodichloromethyl)mercury, which is widely used in the production of dichlorocarbene.^[3] It can be prepared by treating a mixture of chloroform and bromoform with triethyl-benzylammonium chloride and sodium hydroxide.^[3]

Toxicity

According to the CDC, as of 2020^[update], levels that it is normal to be exposed to in drinking water are lower than levels known to cause health problems.^[1] 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.^[1] Studies in animals with much higher levels of the chemical than what humans are normally exposed to have resulted in health problems.^[1] The effects of the chemical on children are unknown but expected to be the same as on adults.^[1]

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.^[4] The Environmental Working Group claims that bromodichloromethane can increase cancer risks and cause harm to reproduction, child development, and fetal growth and development in when present in quantities higher than 0.06 parts per billion (ppb).^[5] This data largely comes from studies reviewed or conducted by the California Office of Environmental Health Hazard Assessment.^[6] As of 2020^[update], the chemical 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.^[1]

Notes

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "ToxFAQs™: Bromodichloromethane". Agency for Toxic Substances and Disease Registry. CDC. Retrieved 2024-08-13.
^ Agency for Toxic Substances & Disease Registry, Accessed 07/10/2012, https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=707&tid=127
^ ^a ^b 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. Vol. 52. 1991. pp. 179–212. ISBN 978-92-832-1252-2.
^ Group, Environmental Working. "EWG's Tap Water Database: Disinfection Byproducts". www.ewg.org. Retrieved 2023-08-08. {{cite web}}: |last= has generic name (help)
^ Group, Environmental Working. "EWG's Tap Water Database: Contaminants in Your Water". www.ewg.org. Retrieved 2023-08-08. {{cite web}}: |last= has generic name (help)
^ "Public Health Goals for Trihalomethanes in Drinking Water" (PDF). oehha.ca.gov. Retrieved 2023-08-08.