Hydrogen bromide

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Hydrogen bromide

General
Systematic name Hydrogen Bromide
Other names
Molecular formula HBr
Molar mass 80.912 g/mol
Appearance Colorless gas.
CAS number
Properties
Density and phase 3.307 g/L, gas.
Solubility in water ? g/100 ml (?°C)
Melting point -86.80°C (186.35 K)
Boiling point -66.38°C (206.77 K)
Acidity (pK_a) ?
Structure
Molecular shape Linear.
Dipole moment 0.82 D
Hazards
MSDS External MSDS
Main hazards Toxic, corrosive.
NFPA 704
Flash point Non-flammable.
R/S statement R: R23, R35, R37.
S: S7, S9, S26, S36,
S37, S39, S45.
RTECS number MW3850000
Supplementary data page
Structure and
properties n, ε_r, etc.
Thermodynamic
data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Other anions HF
HCl
HI
Other cations ?
Related compounds ?
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
[Chemical infoboxInfobox disclaimer and references]

Hydrogen bromide is the diatomic molecule HBr. Under standard conditions, HBr is a gas, but it can be liquified. The aqueous solution hydrobromic acid forms upon dissolving HBr in water. Conversely, HBr can be liberated from hydrobromic acid solutions upon the addition of a dehydration agents. Hydrogen bromide and hydrobromic acid are, therefore, not the same, but they are related. Commonly, chemists refer to hydrobromic acid as "HBr", and this usage, while understood by most chemists, is imprecise and can be confusing to the non-specialist.

Contents

1 Uses of HBr
2 Laboratory synthesis of HBr
3 Industrial preparation
4 References
5 External links

Uses of HBr

There are many uses of HBr in chemical synthesis. For example, HBr is used for the production of alkyl bromides from alcohols:

:ROH + HBr → R⁺OH₂ + Br^- → RBr + H₂O

HBr adds to alkenes to give bromoalkanes:

:RCH=CH₂ + HBr → RCH(Br)-CH₃

HBr adds to alkynes to yield haloalkenes. The stereochemistry of this type of addition is usually anti):

RC≡CH + HBr → RCH(Br)=CH₂

And adds to the haloalkene to form a geminal dihaloalkane This type of addition follows Markovnikov's rule):

:RC(Br)=CH₂ + HBr → RC(Br₂)-CH₃

Also, HBr is used to open epoxides and lactones and in the synthesis of bromoacetals. Additionally, HBr catalyzes many organic reactions.^{1, 2, 3, 4}

Laboratory synthesis of HBr

HBr can synthesized by a variety of methods. A convenient laboratory synthesis entails the reaction between sulfuric acid and NaBr:⁵

:NaBr_(s) + H₂SO_4(aq) → NaHSO_4(s) + HBr_(g)

The bromination of tetraline (1,2,3,4 tetrahydronaphthalene):⁵

:C₁₀H₁₂ + 4Br₂ → C₁₀H₈Br₄ + 4HBr_(g)

Reacting purified hydrogen gas and bromine (in the presence of a platinum catalyst):⁵

:Br₂ + H₂ → 2HBr_(g)

And reducing bromine with phosphorous acid:²

:Br₂ + H₃PO₃ + H₂O → H₃PO_4(s) + 2HBr_(g)

Anhydrous hydrogen bromide can also be produced on a small scale (10 mmol-1 mol) through the thermolysis of triphenylphosphonium bromide in refluxing xylene.¹

HBr prepared by the above methods can be contaminated with Br₂, which can be removed by passing the gas through Cu turnings or through phenol.⁶

Industrial preparation

Unlike hydrogen chloride and hydrochloric acid, which are major industrial chemicals, hydrogen bromide (along with hydrobromic acid) is produced on a much smaller scale. In the primary industrial preparation, hydrogen and bromine are combined at elevated temperatures (200-400 °C). The reaction is typically catalyzed by platinum or asbestos.^2,6

References

(1) Hercouet, M.; LeCorre, (1988) Triphenylphosphonium bromide: A convenient and quantitative source of gaseous hydrogen bromide. Synthesis, 157-158.
(2) Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Butterworth-Heineman: Oxford, Great Britain; 1997; pp. 809-812.
(3) Carlin, William W. U.S. Patent 4,147,601, April 3, 1979.
(4) Vollhardt, K. P. C.; Schore, N. E. Organic Chemistry: Structure and Function; 4th Ed.; W. H. Freeman and Company: New York, NY; 2003.
(5) WebElements: Hydrogen Bromide, URL http://www.webelements.com/webelements/compounds/text/H/Br1H1-10035106.html
(6) Ruhoff, J. R.; Burnett, R. E.; Reid, E. E. "Hydrogen Bromide (Anhydrous)" Organic Syntheses, Vol. 15, p.35 (Coll. Vol. 2, p.338).

External links

For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].

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Hydrogen bromide

General
Systematic name	Hydrogen Bromide
Other names
Molecular formula	HBr
Molar mass	80.912 g/mol
Appearance	Colorless gas.
CAS number
Properties
Density and phase	3.307 g/L, gas.
Solubility in water	? g/100 ml (?°C)
Melting point	-86.80°C (186.35 K)
Boiling point	-66.38°C (206.77 K)
Acidity (pK_a)	?
Structure
Molecular shape	Linear.
Dipole moment	0.82 D
Hazards
MSDS	External MSDS
Main hazards	Toxic, corrosive.
NFPA 704
Flash point	Non-flammable.
R/S statement	R: R23, R35, R37. S: S7, S9, S26, S36, S37, S39, S45.
RTECS number	MW3850000
Supplementary data page
Structure and properties	n, ε_r, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	HF HCl HI
Other cations	?
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) [Chemical infoboxInfobox disclaimer and references]