Tetrabromoethane

Last updated
Tetrabromoethane
Tetrabromoethane.png
Tetrabromoethane.svg
Ball and stick model of tetrabromoethane 1,1,2,2-Tetrabromoethane-3D-balls.png
Ball and stick model of tetrabromoethane
Spacefill model of tetrabromoethane 1,1,2,2-Tetrabromoethane-3D-spacefill.png
Spacefill model of tetrabromoethane
Names
Preferred IUPAC name
1,1,2,2-Tetrabromoethane [1]
Other names
  • Acetylene tetrabromide [2]
  • Muthmann's liquid [3]
  • Tetrabromoacetylene [2]
  • Symmetrical tetrabromoethane [2]
Identifiers
3D model (JSmol)
AbbreviationsTBE [2]
1098321
ChemSpider
ECHA InfoCard 100.001.083 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-191-5
MeSH 1,1,2,2-tetrabromoethane
PubChem CID
RTECS number
  • KI8225000
UNII
UN number 2504
  • InChI=1S/C2H2Br4/c3-1(4)2(5)6/h1-2H X mark.svgN
    Key: QXSZNDIIPUOQMB-UHFFFAOYSA-N X mark.svgN
  • BrC(Br)C(Br)Br
Properties
C2H2Br4
Molar mass 345.654 g·mol−1
AppearanceColourless liquid
Density 2.967 g mL−1
Melting point −1.0 °C; 30.3 °F; 272.2 K
Boiling point 243.6 °C; 470.4 °F; 516.7 K
630 mg L−1 (at 20 °C)
Vapor pressure 10 Pa (at 20 °C)
-123.4·10−6 cm3/mol
1.637
Thermochemistry
165.7 J K−1 mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg
Danger
H319, H330, H412
P260, P273, P284, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 97 °C (207 °F; 370 K)
335 °C (635 °F; 608 K)
Lethal dose or concentration (LD, LC):
  • 1.2 g kg−1(oral, rat) [4]
  • 5.25 g kg−1(dermal, rat)
  • 0.4 g/kg (oral, guinea pig) [4]
  • 0.4 g/kg (oral, rabbit) [4]
  • 0.269 g/kg (oral, mouse) [4]
38 ppm (rat, 4 hr) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1 ppm (14 mg/m3) [2]
REL (Recommended)
None established [2]
IDLH (Immediate danger)
8 ppm [2]
Safety data sheet (SDS) hells-confetti.com
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1,1,2,2-Tetrabromoethane, or simply tetrabromoethane (TBE), is a halogenated hydrocarbon, chemical formula C2H2Br4. Although three bromine atoms may bind to one of the carbon atoms creating 1,1,1,2-tetrabromoethane this is not thermodynamically favorable, so in practice tetrabromoethane is equal to 1,1,2,2-tetrabromoethane, where each carbon atom binds two bromine atoms.

Contents

Uses

It has an unusually high density for an organic compound, near 3 g/mL, due largely to the four bromine atoms. [5] TBE is a liquid at room temperature, and is used to separate mineral ores from its supporting rock by means of preferential flotation. Quartz, feldspar, calcite, dolomite and other minerals with low density will float in TBE, while minerals such as sphalerite, galena and pyrite will sink. A related compound, bromoform, is also sometimes used in these applications, however, TBE is more practical because of its wider liquid range and lower vapor pressure. [5]

Safety

Permissible exposure limit is 1 ppm. [6] Cases of acute TBE poisoning are known as well. [7]

Related Research Articles

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Pentane</span> Alkane with 5 carbon atoms

Pentane is an organic compound with the formula C5H12—that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer, in which case pentanes refers to a mixture of them; the other two are called isopentane (methylbutane) and neopentane (dimethylpropane). Cyclopentane is not an isomer of pentane because it has only 10 hydrogen atoms where pentane has 12.

<span class="mw-page-title-main">Propyne</span> Hydrocarbon compound (HC≡C–CH3)

Propyne (methylacetylene) is an alkyne with the chemical formula CH3C≡CH. It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Bromoform</span> 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 and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.

Dimethylformamide, DMF is an organic compound with the chemical formula HCON(CH3)2. Its structure is HC(=O)−N(−CH3)2. Commonly abbreviated as DMF, this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer. R-11 is not flammable at ambient temperature and pressure but it can become very combustible if heated and ignited by a strong ignition source.

<span class="mw-page-title-main">Chloroprene</span> Chemical compound

Chloroprene (IUPAC name 2-chlorobuta-1,3-diene) is a chemical compound with the molecular formula CH2=CCl−CH=CH2. Chloroprene is a colorless volatile liquid, almost exclusively used as a monomer for the production of the polymer polychloroprene, better known as neoprene, a type of synthetic rubber.

<span class="mw-page-title-main">Bromine pentafluoride</span> Chemical compound

Bromine pentafluoride, BrF5, is an interhalogen compound and a fluoride of bromine. It is a strong fluorinating agent.

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.

<span class="mw-page-title-main">Carbon tetrabromide</span> Chemical compound

Carbon tetrabromide, CBr4, also known as tetrabromomethane, is a bromide of carbon. Both names are acceptable under IUPAC nomenclature.

<span class="mw-page-title-main">Allyl alcohol</span> Organic compound (CH2=CHCH2OH)

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers. Allyl alcohol is the smallest representative of the allylic alcohols.

<i>o</i>-Xylene Chemical compound

o-Xylene (ortho-xylene) is an aromatic hydrocarbon with the formula C6H4(CH3)2, with two methyl substituents bonded to adjacent carbon atoms of a benzene ring (the ortho configuration). It is a constitutional isomer of m-xylene and p-xylene, the mixture being called xylene or xylenes. o-Xylene is a colourless slightly oily flammable liquid.

<span class="mw-page-title-main">Boron tribromide</span> Chemical compound

Boron tribromide, BBr3, is a colorless, fuming liquid compound containing boron and bromine. Commercial samples usually are amber to red/brown, due to weak bromine contamination. It is decomposed by water and alcohols.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

Perchloryl fluoride is a reactive gas with the chemical formula ClO
3
F
. It has a characteristic sweet odor that resembles gasoline and kerosene. It is toxic and is a powerful oxidizing and fluorinating agent. It is the acid fluoride of perchloric acid.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

<span class="mw-page-title-main">Bromochloromethane</span> Chemical compound

Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808.

<span class="mw-page-title-main">Dibromodifluoromethane</span> Chemical compound

Dibromodifluoromethane is a mixed halomethane. It is a colorless non-flammable liquid. Along with Halons 1211, 2402, and 1301, it is one of the most effective fire extinguishers, however, it is also very toxic. It is a class I ozone depleting substance (ODS).

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

References

  1. "1,1,2,2-tetrabromoethane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 26 March 2005. Identification. Retrieved 20 June 2012.
  2. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0009". National Institute for Occupational Safety and Health (NIOSH).
  3. Mellan, Ibert, (1950) Industrial solvents, page 172
  4. 1 2 3 4 5 "Acetylene tetrabromide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. 1 2 Organic based heavy liquids, heavyliquids.com
  6. Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN   978-3527306732.
  7. A B van Haaften (1969). "Acute Tetrabromoethane (Acetylene Tetrabromide) Intoxication in Man". American Industrial Hygiene Association Journal. 30 (3): 251–256. doi:10.1080/00028896909343119. PMID   5793994.