Preparation

Dibromomethane is prepared commercially from dichloromethane via

bromochloromethane Bromochloromethane or methylene bromochloride and Halon 1011 is a mixed halomethane. It is a heavy low-viscosity liquid with refractive index 1.4808. Halon 1011 was invented for use in fire extinguishers in Germany during the mid-1940s, in an atte ...

: :6 CH₂Cl₂ + 3 Br₂ + 2 Al → 6 CH₂BrCl + 2 AlCl₃ :CH₂Cl₂ + HBr → CH₂BrCl + HCl The latter route requires

aluminium trichloride Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms hexahydrate with the formula , containing six water molecules of hydration. Both are colourless crystals, but samples are often contam ...

as a catalyst. The bromochloromethane product from either reaction can further react in a similar manner: :6 CH₂BrCl + 3 Br₂ + 2 Al → 6 CH₂Br₂ + 2 AlCl₃ :CH₂BrCl + HBr → CH₂Br₂ + HCl In the laboratory, it is prepared from

bromoform Bromoform (CHBr3) is a brominated organic solvent, colorless liquid at room temperature, with a high refractive index, very high density, and sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, ...

: :CHBr₃ + Na₃AsO₃ + NaOH → CH₂Br₂ + Na₃AsO₄ + NaBr using

sodium arsenite Sodium arsenite usually refers to the inorganic compound with the formula NaAsO2. Also called sodium ''meta''-arsenite, it is the sodium salt of arsenous acid. Sodium ''ortho''-arsenite is Na3AsO3.Greenwood, N. N.; & Earnshaw, A. (1997). Chemistr ...

and

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

. Another way is to prepare it from

diiodomethane Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly solub ...

and

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 simila ...

Uses

Dibromomethane is used as a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

, gauge fluid, and in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

(often as ¹H-NMR

internal standard An internal standard in analytical chemistry is a chemical substance that is added in a constant amount to samples, the blank and calibration standards in a chemical analysis. This substance can then be used for calibration by plotting the ratio of ...

). It is a convenient agent for converting

catechols Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amount ...

to their

methylenedioxy Methylenedioxy is the term used in the field of chemistry, particularly in organic chemistry, for a functional group with the structural formula R-O-CH2-O-R' which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy gr ...

derivatives.

Natural occurrence

It is naturally produced by marine

algae Algae (; singular alga ) is an informal term for a large and diverse group of photosynthetic eukaryotic organisms. It is a polyphyletic grouping that includes species from multiple distinct clades. Included organisms range from unicellular mic ...

and liberated to the oceans. Releasing on soil causes it to evaporate and leach into the ground. Releasing in water causes it to be lost mainly by

volatilisation Volatilization is the process whereby a dissolved sample is vaporised. In atomic spectroscopy this is usually a two-step process. The analyte is turned into small droplets in a nebuliser which are entrained in a gas flow which is in turn volatilis ...

with a half life of 5.2 hours. It has no significant degradation biological or abiological effects. In the atmosphere it will be lost because of reaction with photochemically produced

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

radicals. The estimated half life of this reaction is 213 days.

References

External links

* {{Halomethanes Bromoalkanes Halomethanes Refrigerants