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Bromoform

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Bromoform
Skeletal formula of bromoform
Skeletal formula of bromoform
Stereo, skeletal formula of bromoform with the explicit hydrogen added
Stereo, skeletal formula of bromoform with the explicit hydrogen added
Spacefill model of bromoform

A bottle of bromoform with some in the adjacent beaker
Names
Preferred IUPAC name Tribromomethane
Other names
  • Bromoform
  • Methenyl tribromide
  • Methyl tribromide
Identifiers
CAS Number
3D model (JSmol)
Abbreviations
  • R-20B3
  • UN 2515
Beilstein Reference 1731048
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.777 Edit this at Wikidata
EC Number
  • 200-854-6
Gmelin Reference 49500
KEGG
MeSH bromoform
PubChem CID
RTECS number
  • PB5600000
UNII
UN number 2515
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CHBr3/c2-1(3)4/h1HKey: DIKBFYAXUHHXCS-UHFFFAOYSA-N
SMILES
  • BrC(Br)Br
Properties
Chemical formula CHBr3
Molar mass 252.731 g·mol
Appearance Colorless liquid
Density 2.89 g/cm
Melting point 8.69 °C; 47.64 °F; 281.84 K
Boiling point 149.40 °C; 300.92 °F; 422.55 K
Solubility in water 3.2 g L (at 30 °C)
log P 2.435
Vapor pressure 670 Pa (at 20.0 °C)
Henry's law
constant (kH) 		17 μmol Pa kg
Acidity (pKa) 13.7
Magnetic susceptibility (χ) -82.60·10 cm/mol
Refractive index (nD) 1.595
Thermochemistry
Heat capacity (C) 130.5 J K mol
Std enthalpy of
formation (ΔfH298) 		6.1–12.7 kJ mol
Std enthalpy of
combustion (ΔcH298) 		−549.1–−542.5 kJ mol
Hazards
GHS labelling:
Pictograms GHS06: Toxic GHS09: Environmental hazard
Signal word Danger
Hazard statements H302, H315, H319, H331, H411
Precautionary statements P261, P273, P305+P351+P338, P311
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3 0 0
Lethal dose or concentration (LD, LC):
LD50 (median dose) 933.0 mg kg (oral, rat)
LDLo (lowest published) 1400 mg/kg (mouse, oral)
1147 mg/kg (rat, oral)
LC50 (median concentration) 1151 ppm (mammal)
LCLo (lowest published) 4282 ppm (rat, 4 hr)
7000 ppm (dog, 1 hr)
NIOSH (US health exposure limits):
PEL (Permissible) TWA 0.5 ppm (5 mg/m)
REL (Recommended) TWA 0.5 ppm (5 mg/m)
IDLH (Immediate danger) 850 ppm
Related compounds
Related alkanes
Supplementary data page
Bromoform (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Bromoform is an organic compound with the chemical formula CHBr3. It is a colorless liquid at room temperature, with a high refractive index and a very high density. Its sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory reagent. It is very slightly soluble in water (one part bromoform in 800 parts water) and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.

Structure

The molecule adopts tetrahedral molecular geometry with C3v symmetry.

Synthesis

Bromoform was discovered in 1832 by Löwig who distilled a mixture of bromal and potassium hydroxide, as analogous to preparation of chloroform from chloral.

Bromoform can be prepared by the haloform reaction using acetone and sodium hypobromite, by the electrolysis of potassium bromide in ethanol, or by treating chloroform with aluminium bromide.

Uses

Only small quantities of bromoform are currently produced industrially in the United States. In the past, it was used as a solvent, sedative and flame retardant, but now it is mainly used as a laboratory reagent, for example as an extraction solvent.

Bromoform's high density makes it useful for separation of minerals by density. When two samples are mixed with bromoform and then allowed to settle, the top layer will contain minerals less dense than bromoform, and the bottom layer will contain denser minerals. Slightly less dense minerals can be separated in the same way by mixing the bromoform with a small amount of a less dense and miscible solvent.

Bromoform is known as an inhibitor of methanogenesis and is a common component of seaweed. Following research by CSIRO and its spin-off FutureFeed, several companies are now growing seaweed, in particular from the genus Asparagopsis, to use as a feed additive for livestock to reduce methane emissions from ruminants.

Occurrence

Bromoform is very commonly made by phytoplankton and seaweeds in the ocean. Bromoform is the most abundant hydrogenated compound in Asparagopsis.

Environment and toxicology

Natural production of bromoform by phytoplankton and seaweeds in the ocean is thought to be its predominant source in the environment. However, locally significant amounts of bromoform enter the environment formed as disinfection byproducts known as trihalomethanes when chlorine is added to drinking water to kill bacteria. It is somewhat soluble in water and readily evaporates into the air. Bromoform is the main trihalomethane produced in beachfront salt water swimming pools with concentrations as high as 1.2 ppm (parts per million). Concentrations in freshwater pools are 1000 times lower. Occupational skin exposure limits are set at 0.5 ppm.

The substance may be hazardous to the environment, and special attention should be given to aquatic organisms. Its volatility and environmental persistence makes bromoform's release, either as liquid or vapor, strongly inadvisable.

Bromoform can be absorbed into the body by inhalation and through the skin. The substance is irritating to the respiratory tract, the eyes, and the skin, and may cause effects on the central nervous system and liver, resulting in impaired functions. Its LD50 is 7.2 mmol/kg in mice, or 1.8 g/kg. The International Agency for Research on Cancer (IARC) concluded that bromoform is not classifiable as to human carcinogenicity. The EPA classified bromoform as a probable human carcinogen.

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 661. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The retained names 'bromoform' for HCBr3, 'chloroform' for HCCl3, and 'iodoform' for HCI3 are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.
  2. ^ NIOSH Pocket Guide to Chemical Hazards. "#0066". National Institute for Occupational Safety and Health (NIOSH).
  3. Rumble, John (18 June 2018). CRC Handbook of Chemistry and Physics. CRC Press. pp. 3–50. ISBN 9781138561632.
  4. ^ "Bromoform". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. George M. Beringer, BROMOFORM (1891) in American Journal of Pharmacy vol 63 p. 82
  6. "Is seaweed the solution to agriculture's methane problem?". Phyconomy. Retrieved 2020-11-13.
  7. ^ Palmer C J and Reason C J (2009), Relationships of surface bromoform concentrations with mixed layer depth and salinity in the tropical oceans (2009), Global Biogeochemical Cycles, 23, GB2014.
  8. Ponte, José M. S.; Seca, Ana M. L.; Barreto, Maria Carmo (9 March 2022). "Asparagopsis Genus: What We Really Know About Its Biological Activities and Chemical Composition". Molecules. 27 (6): 1787. doi:10.3390/molecules27061787. hdl:10400.3/6452. PMID 35335151.
  9. Beech AJ et al (1980) Nitrates, Chlorates and Trihalomethanes in Swimming Pool Water. Am J Public Health, 70(1), 79-82
  10. CDC - NIOSH Pocket Guide to Chemical Hazards
  11. IARC - https://monographs.iarc.fr/wp-content/uploads/2018/06/mono52-10.pdf
  12. ATSDR - https://www.atsdr.cdc.gov/toxfaqs/tf.asp?id=712&tid=128

External links

Halomethanes
Unsubstituted
Monosubstituted
Disubstituted
Trisubstituted
Tetrasubstituted
* Chiral compound.
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