1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an

organobromine compound Organobromine compounds, also called organobromides, are organic compounds that contain carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons avai ...

with the

chemical formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...

. Although trace amounts occur naturally in the

ocean The ocean (also the sea or the world ocean) is the body of salt water that covers approximately 70.8% of the surface of Earth and contains 97% of Earth's water. An ocean can also refer to any of the large bodies of water into which the wo ...

, where it is formed probably by algae and

kelp Kelps are large brown algae seaweeds that make up the order Laminariales. There are about 30 different genera. Despite its appearance, kelp is not a plant - it is a heterokont, a completely unrelated group of organisms. Kelp grows in "underwa ...

, it is mainly synthetic. It is a dense colorless liquid with a faint sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces

hydrogen bromide Hydrogen bromide is the inorganic compound with the formula . 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 tempe ...

gas that is significantly corrosive.

Preparation and use

It is produced by the reaction of ethylene gas with

bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table ( halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simi ...

, in a classic

halogen addition reaction A halogen addition reaction is a simple organic reaction where a halogen molecule is added to the carbon–carbon double bond of an alkene functional group. The general chemical formula of the halogen addition reaction is: :C=C + X2 → X−C−C� ...

: :CH=CH + Br → BrCH–CHBr Historically, 1,2-dibromoethane was used as a component in anti-knock

additives Additive may refer to: Mathematics * Additive function, a function in number theory * Additive map, a function that preserves the addition operation * Additive set-functionn see Sigma additivity * Additive category, a preadditive category with fi ...

in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine with lead deposits.

Pesticide

It has been used as a pesticide in

soil Soil, also commonly referred to as earth or dirt Dirt is an unclean matter, especially when in contact with a person's clothes, skin, or possessions. In such cases, they are said to become dirty. Common types of dirt include: * Debri ...

and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP). Most of these uses have been stopped in the U.S. It continues to be used as a

fumigant Fumigation is a method of pest control or the removal of harmful micro-organisms by completely filling an area with gaseous pesticides—or fumigants—to suffocate or poison the pests within. It is used to control pests in buildings (s ...

for treatment of logs for

termite Termites are small insects that live in colonies and have distinct castes (eusocial) and feed on wood or other dead plant matter. Termites comprise the infraorder Isoptera, or alternatively the epifamily Termitoidae, within the order Blatto ...

s and

beetle Beetles are insects that form the order Coleoptera (), in the superorder Endopterygota. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 400,000 describ ...

s, for control of

moth Moths are a paraphyletic group of insects that includes all members of the order Lepidoptera that are not butterflies, with moths making up the vast majority of the order. There are thought to be approximately 160,000 species of moth, many of w ...

s in

beehives A beehive is an enclosed structure in which some honey bee species of the subgenus '' Apis'' live and raise their young. Though the word ''beehive'' is commonly used to describe the nest of any bee colony, scientific and professional literature ...

Reagent

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

fire retardant A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability of fuels or delay their combustion. Fire retardants m ...

s. In organic synthesis, 1,2-dibromoethane is used as a source of bromine to brominate carbanions and to activate

magnesium Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ta ...

for certain Grignard reagents. In the latter process, 1,2-dibromoethane reacts with magnesium, producing

ethene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

and magnesium bromide, and exposes a freshly etched portion of magnesium to the substrate.

Health effects

1,2-Dibromoethane causes changes in the metabolism and severe destruction of living tissues. The known empirical LD50 values for 1,2-dibromoethane are 140 mg kg⁻¹ (oral, rat), and 300.0 mg kg⁻¹ (dermal, rabbit). 1,2-Dibromoethane is a known

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index. The

effects Effect may refer to: * A result or change of something ** List of effects ** Cause and effect, an idiom describing causality Pharmacy and pharmacology * Drug effect, a change resulting from the administration of a drug ** Therapeutic effect, a ...

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. 1,2-Dibromoethane is not known to cause

birth defect A birth defect, also known as a congenital disorder, is an abnormal condition that is present at birth regardless of its cause. Birth defects may result in disabilities that may be physical, intellectual, or developmental. The disabilities ca ...

s in humans. Swallowing has caused death at 40ml doses.

References

External links

National Pollutant Inventory 1,2-Dibromoethane Fact Sheet

Congressional Research Service (CRS) Reports regarding Ethylene Dibromide

ATSDR ToxFAQs

{{DEFAULTSORT:Dibromoethane, 1, 2- Endocrine disruptors Insecticides Bromoalkanes Fumigants Flame retardants Hazardous air pollutants Fuel additives IARC Group 2A carcinogens Sweet-smelling chemicals