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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	[10035-10-6]
Properties
Density and phase	3.307 g/L, gas.
Solubility in water	193 g/100 ml (20 °C)
Melting point	–86.80°C (186.35 K)
Boiling point	–66.38°C (206.77 K)
Critical point	Tcrit = 90°C Pcrit = 8.5 MPa
Acidity (pKa)	≈ –9
Structure
Molecular shape	Linear.
Dipole moment	0.82 D
Hazards
MSDS	hydrobromic acid hydrogen bromide
Main hazards	Toxic, corrosive.
NFPA 704	0 3 1
Flash point	Non-flammable.
R/S statement	R: R23, R35, R37. S: S7, S9, S26, S36, S37, S39, S45.
RTECS number	MW3850000
Thermodynamic data
Standard enthalpy of formation	ΔfH0 (gas) = –36.3 kJ/mol ΔfH0 (aq, ∞) = –121.0 kJ/mol
Heat of vaporization	ΔHvap = 217 J/g
Heat of fusion	ΔHfus = 29.8 J/g
Heat of solution	ΔHsol = –83.7 kJ/mol
Supplementary data page
Structure and properties	n, εr, 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) Infobox 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 General Description 2 Uses of HBr 3 Laboratory synthesis of HBr 4 Industrial preparation 5 References 6 External links

At room temperature, HBr is a nonflammable gas with an acrid odor, fuming in moist air because of the formation of hydrobromic acid. HBr is very soluble in water, forming hydrobromic acid solution, which is saturated at 68.85% HBr by weight at room temperature. Hydrobromic acid is almost completely dissociated into H⁺ and Br^– in aqueous solution. Aqueous solutions that are 47.38% HBr by weight form a constant-boiling mixture (reverse azeotrope) that boils at 126°C. Boiling a solution that is more concentrated than this causes HBr to boil in excess until the constant boiling mixture is reached. Boiling solutions less concentrated causes H₂O to boil in excess until the constant boiling mixture is reached.

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]

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)

However, this synthetic process is ineffective as HBr formed will be oxidized to bromine gas by sulfuric acid:

2HBr_(g) + H₂SO_4(aq) → Br_2(g) + SO_2(g) + 2H₂O_(l)

Alternatively, it can be prepared by 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]

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]

1. ^ ^{a b} Hercouet, A.;LeCorre, M. (1988) Triphenylphosphonium bromide: A convenient and quantitative source of gaseous hydrogen bromide. Synthesis, 157-158.
2. ^ ^{a b} 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 4147601 , 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. ^ ^{a b c} WebElements: Hydrogen Bromide
6. ^ ^{a b} Ruhoff, J. R.; Burnett, R. E.; Reid, E. E. "Hydrogen Bromide (Anhydrous)" Organic Syntheses, Vol. 15, p.35 (Coll. Vol. 2, p.338).

• Links to external chemical sources