1,2-Dibromoethane

Last updated
1,2-Dibromoethane
Skeletal formula of 1,2-dibromoethane 1,2-Dibromoethane v2.svg
Skeletal formula of 1,2-dibromoethane
Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added Valence structural formula of 1,2-dibromoethane.svg
Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added
1,2-dibromoethane-3D-vdW.png
Names
Preferred IUPAC name
1,2-Dibromoethane [1]
Other names
  • Ethylene dibromide [1]
  • Ethylene bromide [2]
  • Glycol bromide [2]
  • Di(bromomethyl)
Identifiers
3D model (JSmol)
AbbreviationsEDB[ citation needed ]
605266
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.132 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-444-5
KEGG
MeSH Ethylene+Dibromide
PubChem CID
RTECS number
  • KH9275000
UNII
UN number 1605
  • InChI=1S/C2H4Br2/c3-1-2-4/h1-2H2 Yes check.svgY
    Key: PAAZPARNPHGIKF-UHFFFAOYSA-N Yes check.svgY
  • BrCCBr
Properties
C2H4Br2
Molar mass 187.862 g·mol−1
AppearanceColorless liquid
Odor faintly sweet [2]
Density 2.18 g mL−1
Melting point 9.4 to 10.2 °C; 48.8 to 50.3 °F; 282.5 to 283.3 K
Boiling point 129 to 133 °C; 264 to 271 °F; 402 to 406 K
0.4% (20 °C) [2]
log P 2.024
Vapor pressure 1.56 kPa
14 μmol Pa kg−1
1.539
Thermochemistry
134.7 J K−1 mol−1
Std molar
entropy (S⦵298)
223.30 J K−1 mol−1
−1.2419–−1.2387 MJ mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
carcinogen [2]
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H311, H315, H319, H331, H335, H350, H411
P261, P273, P280, P301+P310, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
Flash point 104 °C (219 °F; 377 K)
Lethal dose or concentration (LD, LC):
  • 55.0 mg kg−1(oral, rabbit)
  • 79.0 mg kg−1(oral, chicken)
  • 110.0 mg kg−1(oral, guinea pig)
  • 130.0 mg kg−1(oral, quail)
  • 300.0 mg kg−1(dermal, rabbit)
1831 ppm (rat, 30 min)
691 ppm (rat, 1 hr) [3]
200 ppm (rat, 8 hr)
400 ppm (guinea pig, 3 hr) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak] [2]
REL (Recommended)
Ca TWA 0.045 ppm C 0.13 ppm [15-minute] [2]
IDLH (Immediate danger)
Ca [100 ppm] [2]
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 ?)

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2H
4Br
2. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversial fumigant. [4] The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive. [5]

Contents

Preparation and use

It is produced by the reaction of ethylene gas with bromine, [6] in a classic halogen addition reaction:

CH2=CH2 + Br2 → BrCH2–CH2Br

Historically, 1,2-dibromoethane was used as a component in anti-knock additives in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine with lead deposits. [7]

Pesticide

It has been used as a pesticide in soil and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP). [4] Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for termites and beetles, and for control of moths in beehives. [8]

Reagent

1,2-Dibromoethane has wider applications in the preparation of other organic compounds including those carrying modified diazocine rings [9] and vinyl bromide that is a precursor to some fire retardants. [4]

In organic synthesis, 1,2-dibromoethane is used to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, 1,2-dibromoethane reacts with magnesium, producing ethylene and magnesium bromide, which are innocuous, exposing a more active portion of the magnesium particle to the substrate. [10]

Health effects

1,2-Dibromoethane causes changes in the metabolism and severe destruction of living tissues. [5] The known empirical LD50 values for 1,2-dibromoethane are 140 mg kg−1 (oral, rat), and 300.0 mg kg−1 (dermal, rabbit). [5] 1,2-Dibromoethane is a known carcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index. [11]

The effects on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain. Changes in the brain and behavior were also seen in young rats whose male parents had breathed 1,2-dibromoethane, and birth defects were observed in the young of animals that were exposed while pregnant. [12] 1,2-Dibromoethane is not known to cause birth defects in humans. Swallowing has caused death at 40ml doses. [8]

Related Research Articles

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

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s. From the chemistry perspective, it is one of the halomethanes.

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

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. It is an example of a cycloalkene. At room temperature, cyclohexene a colorless liquid with a sharp odor. It has few practical applications.

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

Hydrogen bromide is the inorganic compound with the formula HBr. It is a hydrogen halide consisting of hydrogen and bromine. A colorless gas, it dissolves in water, forming hydrobromic acid, which is saturated at 68.85% HBr by weight at room temperature. Aqueous solutions that are 47.6% HBr by mass form a constant-boiling azeotrope mixture that boils at 124.3 °C (255.7 °F). Boiling less concentrated solutions releases H2O until the constant-boiling mixture composition is reached.

<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.

The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.

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

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

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

Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, perfumes and other organic compounds. Allyl bromide is a colorless liquid, although commercial samples appear yellow or brown. It is an irritant and a potentially dangerous alkylating agent. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.

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

Vinyl fluoride is an organic halide with the chemical formula C2H3F. It is a colorless gas with a faint ether-like odor. It is used as the monomeric precursor to the fluoropolymer polyvinylfluoride.

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

Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.

1,1-Dibromoethane is a clear, slightly brown, flammable chemical compound. It is classified as the organobromine compound, and has the chemical formula C2H4Br2 and it is a position isomer of 1,2-dibromoethane. It is commonly seen in industrial chemistry, where it is used as a fuel additive. It is also used as a grain and soil fumigant for insect control.

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

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

Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.

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

Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.

References

  1. 1 2 "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 657. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0270". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "Ethylene dibromide". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 Yoffe, David; Frim, Ron; Ukeles, Shmuel D.; Dagani, Michael J.; Barda, Henry J.; Benya, Theodore J.; Sanders, David C. (2013). "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–31. doi:10.1002/14356007.a04_405.pub2. ISBN   978-3-527-30385-4.
  5. 1 2 3 "Safety Data Sheet for CAS-No.:106-93-4 Ethylene dibromide".
  6. ↑ "Preparation and purification of 1,2-dibromoethane" (PDF). Synlett. 28: 49–51. 2017.
  7. ↑ Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics . 22 (25): 5154–5178. doi:10.1021/om030621b.
  8. 1 2 "Toxicological Profile for 1,2-Dibromoethane" (PDF). Archived from the original (PDF) on 2009-11-22. Retrieved 2009-11-22.
  9. ↑ Hamada, Y.; Mukai. S. (1996). "Synthesis of ethano-Tröger's base, configurationally stable substitute of Tröger's base". Tetrahedron Asymmetry. 7 (9): 2671–2674. doi:10.1016/0957-4166(96)00343-6.
  10. ↑ Maynard, G. D. (2004). "1,2-Dibromoethane". In Paquette, L. (ed.). Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289X.rd039. ISBN   0471936235.
  11. ↑ "Ranking Possible Cancer Hazards from Rodent Carcinogens" (PDF). Archived from the original (PDF) on 2019-06-29.
  12. ↑ "Toxic Substances Portal – 1,2-Dibromoethane".
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.