Hydrogen bromide

Reactions

Organic chemistry

Hydrogen bromide and hydrobromic acid are important reagents in the production of organobromine compounds. In an electrophilic addition reaction, HBr adds to alkenes: : The resulting alkyl bromides are useful alkylating agents, e.g., as precursors to fatty amine derivatives. Related free radical additions to allyl chloride and styrene give 1-bromo-3-chloropropane and phenylethylbromide, respectively.

Hydrogen bromide reacts with dichloromethane to give bromochloromethane and dibromomethane, sequentially: : : These metathesis reactions illustrate the consumption of the stronger acid (HBr) and release of the weaker acid (HCl).

Allyl bromide is prepared by treating allyl alcohol with HBr: :

HBr adds to alkynes to yield bromoalkenes. The stereochemistry of this type of addition is usually anti: : RC≡CH + HBr → RC(Br)=CH2

Also, HBr adds epoxides and lactones, resulting in ring-opening.

With triphenylphosphine, HBr gives triphenylphosphonium bromide, a solid "source" of HBr. :

Inorganic chemistry

Vanadium(III) bromide and molybdenum(IV) bromide were prepared by treatment of the higher chlorides with HBr. These reactions proceed via redox reactions:

:

Industrial preparation

Hydrogen bromide (along with hydrobromic acid) is produced by combining hydrogen and bromine at temperatures between 200 and 400 °C. The reaction is typically catalyzed by platinum or asbestos.

Laboratory synthesis

HBr can be prepared by distillation of a solution of sodium bromide or potassium bromide with phosphoric acid or sulfuric acid: : KBr + H2SO4 → KHSO4 + HBr

Concentrated sulfuric acid is less effective because it oxidizes HBr to bromine: : 2 HBr + H2SO4 → Br2 + SO2 + 2 H2O

The acid may be prepared by:

• reaction of bromine with water and sulfur:
• : 2 Br2 + S + 2 H2O → 4 HBr + SO2
• bromination of tetralin:
• : C10H12 + 4 Br2 → C10H8Br4 + 4 HBr
• reduction of bromine with phosphorous acid:
• : Br2 + H3PO3 + H2O → H3PO4 + 2 HBr Anhydrous hydrogen bromide can also be produced on a small scale by thermolysis of triphenylphosphonium bromide in refluxing xylene.

Hydrogen bromide prepared by the above methods can be contaminated with Br2, which can be removed by passing the gas through a solution of phenol at room temperature in tetrachloromethane or other suitable solvent (producing 2,4,6-tribromophenol and generating more HBr in the process) or through copper turnings or copper gauze at high temperature.

Safety

HBr is highly corrosive and, if inhaled, can cause lung damage.{{cite web | access-date = 2024-02-09

References

References

1. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". The [[Royal Society of Chemistry]].
2. {{RubberBible87th
3. (2016). "Acidity of Strong Acids in Water and Dimethyl Sulfoxide". The Journal of Physical Chemistry A.
4. Perrin, D. D. Dissociation constants of inorganic acids and bases in aqueous solution. Butterworths, London, 1969.
5. Zumdahl, Steven S.. (2009). "Chemical Principles 6th Ed.". Houghton Mifflin Company.
6. {{PGCH. 0331
7. {{IDLH. 10035106. Hydrogen bromide
8. Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C.. "Bromine Compounds".
9. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Butterworth-Heineman: Oxford, Great Britain; 1997; pp. 809–812.
10. Vollhardt, K. P. C.; [[Neil E. Schore. Schore, N. E.]] Organic Chemistry: Structure and Function; 4th Ed.; W. H. Freeman and Company: New York, NY; 2003.
11. Hercouet, A.; LeCorre, M. (1988) Triphenylphosphonium bromide: A convenient and quantitative source of gaseous hydrogen bromide. Synthesis, 157–158.
12. (1993). "Low-Temperature Syntheses of Vanadium(III) and Molybdenum(IV) Bromides by Halide Exchange". J. Chem. Soc., Dalton Trans..
13. M. Schmeisser "Chlorine, Bromine, Iodine" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 282.
14. Ruhoff, J. R.; Burnett, R. E.; Reid, E. E. [http://www.orgsyn.org/demo.aspx?prep=CV2P0338 "Hydrogen Bromide (Anhydrous)"] Organic Syntheses, Vol. 15, p. 35 (Coll. Vol. 2, p. 338).