Bromoform

Bromoform

Names
Preferred IUPAC name Tribromomethane[1]
Other names Bromoform[1] Methenyl tribromide[citation needed] Methyl tribromide[2] Tribromomethane[2]
Identifiers
CAS Number	75-25-2 Y
3D model (JSmol)	Interactive image
Abbreviations	R-20B3[citation needed] UN 2515[citation needed]
Beilstein Reference	1731048
ChEBI	CHEBI:38682 Y
ChEMBL	ChEMBL345248 Y
ChemSpider	13838404 Y
DrugBank	DB03054 Y
ECHA InfoCard	100.000.777
EC Number	200-854-6
Gmelin Reference	49500
KEGG	C14707 Y
MeSH	bromoform
PubChem CID	5558
RTECS number	PB5600000
UNII	TUT9J99IMU Y
UN number	2515
InChI InChI=1S/CHBr3/c2-1(3)4/h1H Y Key: DIKBFYAXUHHXCS-UHFFFAOYSA-N Y
SMILES BrC(Br)Br
Properties
Chemical formula	CHBr3
Molar mass	7002252731000000000♠252.731 g·mol−1
Appearance	Colorless liquid
Density	2.89 g mL−1
Melting point	−4 to 16 °C; 25 to 61 °F; 269 to 289 K
Boiling point	147 to 151 °C; 296 to 304 °F; 420 to 424 K
Solubility in water	3.2 g L−1 (at 30 °C)
log P	2.435
Vapor pressure	670 Pa (at 20.0 °C)
Henry's law constant (kH)	17 μmol Pa−1 kg−1
Acidity (pKa)	13.7
Magnetic susceptibility (χ)	-82.60·10−6 cm3/mol
Refractive index (nD)	1.595
Thermochemistry
Heat capacity (C)	130.5 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	6.1–12.7 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−549.1–−542.5 kJ mol−1
Hazards
Safety data sheet	See: data page
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H302, H315, H319, H331, H411
GHS precautionary statements	P261, P273, P305+351+338, P311
NFPA 704	0 3 0
Lethal dose or concentration (LD, LC):
LD50 (median dose)	933.0 mg kg−1(oral, rat)
LDLo (lowest published)	1400 mg/kg (mouse, oral) 1147 mg/kg (rat, oral)[3]
LC50 (median concentration)	1151 ppm (mammal)[3]
LCLo (lowest published)	4282 ppm (rat, 4 hr) 7000 ppm (dog, 1 hr)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 0.5 ppm (5 mg/m3) [skin][2]
REL (Recommended)	TWA 0.5 ppm (5 mg/m3) [skin][2]
IDLH (Immediate danger)	850 ppm[2]
Related compounds
Related alkanes	Dibromomethane Tetrabromomethane 1,1-Dibromoethane 1,2-Dibromoethane Tetrabromoethane
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
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

Bromoform (CHBr₃) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is a trihalomethane, and is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. 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. Currently its main use is as a laboratory reagent.

A bottle of bromoform with some in the adjacent beaker

Contents

• 
  1 Structure
  


• 
  2 Uses
  


• 
  3 Environment and Toxicology
  


• 
  4 References
  


• 
  5 External links
  

Structure

The molecule adopts tetrahedral molecular geometry with C_3vsymmetry.

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 fully miscible solvent.

Environment and Toxicology

Natural production of bromoform by phytoplankton and seaweeds in the ocean is thought to be its predominant source in the environment.^[4] 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.^[5] Occupational skin exposure limits are set at 0.5 ppm.^[6]

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. It is soluble in about 800 parts water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone, and oils. Its LD₅₀ is 7.2 mmol/kg in mice, or 1.8g/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.^[7][8]

References

• 
  Betterton E. A.; Arnold R. G.; Kuhler R. J.; Santo G. A. (June 2005). "Reductive dehalogenation of bromoform in aqueous solution". Environ. Health Perspect. Brogan &#38. 103: 89–91(3). doi:10.2307/3432487. JSTOR 3432487. PMC 1519304. PMID 8565919..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
  PDF
  


• U.S. Department of Health and Human Services. Toxicological Profile for Bromoform and Dibromochloromethane [1]. August 2005.

1. 
   ^ ^ab 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. 
   ^ ^abcde NIOSH Pocket Guide to Chemical Hazards. "#0066". National Institute for Occupational Safety and Health (NIOSH).
   


3. 
   ^ ^abc "Bromoform". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
   


4. 
   ^ 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.
   


5. 
   ^ Beech AJ et al (1980) Nitrates, Chlorates and Trihalomethanes in Swimming Pool Water. Am J Public Health, 70(1), 79-82
   


6. 
   ^ CDC - NIOSH Pocket Guide to Chemical Hazards
   


7. 
   ^ IARC - https://monographs.iarc.fr/wp-content/uploads/2018/06/mono52-10.pdf
   


8. 
   ^ ATSDR - https://www.atsdr.cdc.gov/toxfaqs/tf.asp?id=712&tid=128
   

External links

• International Chemical Safety Card 0108


• 
  NIOSH Pocket Guide to Chemical Hazards. "#0066". National Institute for Occupational Safety and Health (NIOSH).
  


• Entry at chemicalland21.com


• Toxicological profile for bromoform and dibromochlormethane


• Toxicity summary


• IARC Summaries & Evaluations: Vol. 62 (1991), Vol. 71 (1999)
  


• ChemSub Online: Bromoform

v t e Halomethanes
Monosubstituted	CH3F CH3Cl CH3Br CH3I
Disubstituted	CH2F2 CH2ClF CH2BrF CH2FI CH2Cl2 CH2BrCl CH2ClI CH2Br2 CH2BrI CH2I2
Trisubstituted	CHF3 CHClF2 CHBrF2 CHF2I CHCl2F C*HBrClF C*HClFI CHBr2F C*HBrFI CHFI2 CHCl3 CHBrCl2 CHCl2I CHBr2Cl C*HBrClI CHClI2 CHBr3 CHBr2I CHBrI2 CHI3
Tetrasubstituted	CF4 CClF3 CBrF3 CF3I CCl2F2 CBrClF2 CClF2I CBr2F2 CBrF2I CF2I2 CCl3F CBrCl2F CCl2FI CBr2ClF C*BrClFI CClFI2 CBr3F CBr2FI CBrFI2 CFI3 CCl4 CBrCl3 CCl3I CBr2Cl2 CBrCl2I CCl2I2 CBr3Cl CBr2ClI CBrClI2 CClI3 CBr4 CBr3I CBr2I2 CBrI3 CI4 CAt4
* Chiral compound.

Authority control	GND: 4306315-9

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