User:MaryGrace J. Larsen/Bromoethane



Original Article:

Not to be confused with Ethidium bromide.

''Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor.''

Preparation[edit]
''The preparation of EtBr stands as a model for the synthesis of bromoalkanes in general. It is usually prepared by the addition of HBr to ethene:''


 * H2C=CH2 + HBr → H3C-CH2Br

''Bromoethane is inexpensive and would rarely be prepared in the laboratory. A laboratory synthesis includes reacting ethanol with a mixture of hydrobromic and sulfuric acids. An alternate route involves refluxing ethanol with phosphorus and bromine; phosphorus tribromide is generated in situ.''

Uses[edit]
''In organic synthesis, EtBr is the synthetic equivalent of the ethyl carbocation (Et+) synthon. In reality, such a cation is not actually formed. For example, carboxylates salts are converted to ethyl esters, carbanions to ethylated derivatives, thiourea into ethylisothiouronium salts, and amines into ethylamines.''

Safety[edit]
''Short chain monohalocarbons in general are potentially dangerous alkylating agents. Bromides are better alkylating agents than chlorides, thus exposure to them should be minimized. EtBr is classified by the State of California as carcinogenic and a reproductive toxin.[ citation needed] '' (**remove, found contradicting evidence https://oehha.ca.gov/media/downloads/proposition-65/chemicals/083112nsrltsd.pdf )

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My edits/additions:

= Bromoethane =

IUPAC Name:
bromoethane

Other names:
1-bromoethane, ethyl bromide, bromic ether, hydrobromic ether, and monobromoethane.

Molecular formulae:
C2H5Br or CH3CH2Br

Molar mass:
108.97 g/mol

Physical characteristics:
colorless to yellow, volatile liquid at STP (standard temperature and pressure)

Boiling point:
38.4°C

Melting point:
-118.4°C

Flash point:
-20°C

Density:
1.46 g/cm3 at 20°C

Uses and Applications
Bromoethane has a variety of possible applications. It is used in laboratory settings, often for organic syntheses. It can be used in the manufacture of agricultural chemicals such as pesticides and fertilizers. And, bromoethane can also be used in water treatment.

Synthesis of bromoethane: (include photos of synthetic schemes with structure and steps/electron flow)
Bromoethane is a type of organic compound called an alkyl halide, meaning it is a hydrocarbon with a halogen attached to one of the carbons.

One way to produce alkyl halides is through an addition reaction of an alkene, a hydrocarbon with a double bond between two of the carbons. An alkene will react with a hydrogen halide to produce an alkyl halide. In this case, ethene (alkene) will undergo the addition of bromic acid (hydrogen halide) to form bromoethane (alkyl halide).

HBr + CH2CH2 → CH3CH2Br

Another way of producing alkyl halides is to react an alcohol with a hydrogen halide producing both an alkyl halide and water. In this case, bromic acid (hydrogen halide) and ethanol (alcohol) react to produce bromoethane (alkyl halide) and water

HBr + CH3CH2OH → CH3CH2Br + H2O    (Patent CN106397102A)

Safety and Hazards (include photo of pictograms and NFPA diamond)
Bromoethane can pose several health and safety risks. It is highly flammable as both a vapor and a liquid. A person can experience acute toxicity if bromomethane in ingested or inhaled. Bromoethane has shown carcinogenic effects towards animals.