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

organobromine compound 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 bromometh ...

with the

chemical formula 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 symbols, such as pare ...

. Although trace amounts occur naturally in the

ocean The ocean is the body of salt water that covers approximately 70.8% of Earth. The ocean is conventionally divided into large bodies of water, which are also referred to as ''oceans'' (the Pacific, Atlantic, Indian Ocean, Indian, Southern Ocean ...

, where it is probably formed by

algae Algae ( , ; : alga ) is an informal term for any organisms of a large and diverse group of photosynthesis, photosynthetic organisms that are not plants, and includes species from multiple distinct clades. Such organisms range from unicellular ...

and

kelp Kelps are large brown algae or seaweeds that make up the order (biology), order Laminariales. There are about 30 different genus, genera. Despite its appearance and use of photosynthesis in chloroplasts, kelp is technically not a plant but a str ...

, 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 Fumigation is a method of pest control or the removal of harmful microorganisms 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 (structural ...

. 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 temper ...

gas that is significantly corrosive.

Preparation and use

It is produced by the reaction of

ethylene 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 bond, carbon–carbon doub ...

gas with

bromine Bromine is a chemical element; it has chemical symbol, symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between th ...

, 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-function see Sigma additivity * Additive category, a preadditive category with fin ...

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 Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

soil Soil, also commonly referred to as earth, is a mixture of organic matter, minerals, gases, water, and organisms that together support the life of plants and soil organisms. Some scientific definitions distinguish dirt from ''soil'' by re ...

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

for treatment of logs for

termite Termites are a group of detritivore, detritophagous Eusociality, eusocial cockroaches which consume a variety of Detritus, decaying plant material, generally in the form of wood, Plant litter, leaf litter, and Humus, soil humus. They are dist ...

s and

beetle Beetles are insects that form the Taxonomic rank, order Coleoptera (), in the superorder Holometabola. Their front pair of wings are hardened into wing-cases, elytra, distinguishing them from most other insects. The Coleoptera, with about 40 ...

s, and for control of

moth Moths are a group of insects that includes all members of the order Lepidoptera that are not Butterfly, butterflies. They were previously classified as suborder Heterocera, but the group is Paraphyly, paraphyletic with respect to butterflies (s ...

s in

beehives A beehive is an enclosed structure which houses honey bees, subgenus '' Apis.'' Honey bees live in the beehive, raising their young and producing honey as part of their seasonal cycle. Though the word ''beehive'' is used to describe the nest of ...

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 ...

s. In

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

, 1,2-dibromoethane is used to brominate

carbanion In organic chemistry, a carbanion is an anion with a lone pair attached to a tervalent carbon atom. This gives the carbon atom a negative charge. Formally, a carbanion is the conjugate base of a carbon acid: : where B stands for the base (chemist ...

s and to activate

magnesium Magnesium is a chemical element; it has Symbol (chemistry), 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 ...

for certain

Grignard reagent Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...

s. In the latter process, 1,2-dibromoethane reacts with magnesium, producing

and

magnesium bromide Magnesium bromide are inorganic compounds with the chemical formula , where x can range from 0 to 9. They are all white deliquescent solids. Some magnesium bromides have been found naturally as rare minerals such as: bischofite and carnallite.Gruy ...

, which are innocuous, exposing a more active portion of the magnesium particle to the substrate.

Health effects

1,2-Dibromoethane causes changes in the

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

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 agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

, 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, ...

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 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 can range from mild to severe. Birth de ...

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 Fuel additives IARC Group 2A carcinogens Sweet-smelling chemicals