Bromine azide: Difference between revisions
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Bromium azide adds to alkenes both through ionic and free-radical addition, each giving an opposite orientation in the products. The ionic addition occurs stereospecifically in trans. <ref>{{cite journal|last=Liu|first=Robert|title=2,3-Bis(perfluormethyl)bicyclo2.2.2]octa-2,5,7-trienes and their photorearrangement reactions|journal=J.Am.Chem.Soc.|year=1968|volume=90|issue=1|pages=215-216|doi=10.1021/ja01003a041|url=http://dx.doi.org/10.1021/ja01003a041|accessdate=10/19/2012}}</ref> |
Bromium azide adds to alkenes both through ionic and free-radical addition, each giving an opposite orientation in the products. The ionic addition occurs stereospecifically in trans. <ref>{{cite journal|last=Liu|first=Robert|title=2,3-Bis(perfluormethyl)bicyclo2.2.2]octa-2,5,7-trienes and their photorearrangement reactions|journal=J.Am.Chem.Soc.|year=1968|volume=90|issue=1|pages=215-216|doi=10.1021/ja01003a041|url=http://dx.doi.org/10.1021/ja01003a041|accessdate=10/19/2012}}</ref> |
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Reactions involving bromine azide are difficult to work with. The molecule is very reactive and is known to explode easily. This makes it a key reagent in explosives.<ref>{{cite book|first=ed. by Dale L. Perry|title=Handbook of inorganic compounds|year=1995|publisher=CRC Press|location=Boca Raton [u.a.]|isbn=0849386713|pages=74|url=http://www.amazon.com/Handbook-Inorganic-Compounds-Dale-Perry/dp/0849386713}}</ref> |
Reactions involving bromine azide are difficult to work with. The molecule is very reactive and is known to explode easily. This makes it a key reagent in explosives.<ref>{{cite book|first=ed. by Dale L. Perry|title=Handbook of inorganic compounds|year=1995|publisher=CRC Press|location=Boca Raton [u.a.]|isbn=0849386713|pages=74|url=http://www.amazon.com/Handbook-Inorganic-Compounds-Dale-Perry/dp/0849386713}}</ref> |
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Photochemistry experiments with Bromine azide has found that UV photolysis of a small sample of bromine azide resulted in dissociation of the entire sample, making it unstable. Similar samples with azide molecules did not show such an effect. From this we can rationalize bromine azide's unstable tendencies.<ref>{{cite journal|last=Henshaw|first=T. L.|coauthors=David, S. J.; MacDonald, M. A.; Gilbert, J. V.; Stedman, D. H.; Coombe, R. D.|title=Collisional decomposition of bromine azide|journal=The Journal of Physical Chemistry|date=1 April 1987|volume=91|issue=9|pages=2287–2293|doi=10.1021/j100293a016}}</ref> |
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==Safety== |
==Safety== |
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Revision as of 05:00, 17 November 2012
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| Names | |
|---|---|
| IUPAC name
Bromine azide
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| Other names
Bromine nitride, Nitrogen bromide, Azidobromide
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| Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| BrN3 | |
| Molar mass | 121.924 g/mol |
| Appearance | Red liquid |
| Density | N/A |
| Melting point | -45 degrees C |
| Boiling point | Explodes |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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This is a poison that can spontaneously explode.[1] It explodes on contact with arsenic, sodium, silver foil, or phosphorus. It has a hazard class of 1.1A. |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Properties
Bromine azide has been described as a crystal or a red liquid at room temperature. It is extremely sensitive to small variations in temperature and pressure, thus extreme caution must be observed when working with this reagent. This property of bromine azide has led to difficulty in discerning its crystal structure, with explosions occurring at Δp ≥ 0.05 Torr and also upon crystallization. Despite this, a crystal structure of bromine azide has been obtained using a miniature zone-melting procedure with focused infrared laser radiation. In contrast to IN3, which forms an endless chain-like structure upon crystallization, BrN3 forms a helical structure.[2]
Production
Bromine azide is produced through the reaction of sodium azide with Br2. This reaction forms bromine azide and sodium bromide. [2]
Reactions
Bromium azide adds to alkenes both through ionic and free-radical addition, each giving an opposite orientation in the products. The ionic addition occurs stereospecifically in trans. [3] Reactions involving bromine azide are difficult to work with. The molecule is very reactive and is known to explode easily. This makes it a key reagent in explosives.[4] Photochemistry experiments with Bromine azide has found that UV photolysis of a small sample of bromine azide resulted in dissociation of the entire sample, making it unstable. Similar samples with azide molecules did not show such an effect. From this we can rationalize bromine azide's unstable tendencies.[5]
Safety
Great care must be taken when handling bromine azide as it is potentially toxic and is able to explode under various conditions. Concentrated solutions in organic solvents may also explode. The liquid explodes on contact with arsenic, sodium, silver foil, or phosphorus. When heated to decomposition it emits highly toxic fumes of Br− and explodes. The amount of compound used during experimentation should be limited to 2 mmol. It also poses a potential moderate fire hazard in the form of vapor by chemical reaction. It is also a powerful oxidant. Safety shields, safety glasses, face shields, leather gloves, and protective clothing such as leather suits and ear plugs should be worn for protection in the event of an explosion. Teflon containers should be used whenever possible to prevent hazardous fragmentation.The extinguishing agent of Bromine Azide (CAS NO.13973-87-0) are dry powder, foam, sand, carbon dioxide, water mist.[6]
References
- ^ Patnaik, Pradyot (2007). A Comprehensive Guide to the Hazardous Properties of Chemical Substances. 615: Wiley-Interscience. p. 615. ISBN 0-471-71458-5.
{{cite book}}: CS1 maint: location (link) - ^ a b Lyhs, Benjamin (20 February 2012). "Solid-State Structure of Bromine Azide". Angewandte Chemie International Edition. 51 (8): 1970–1974. doi:10.1002/anie.201108092.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ Liu, Robert (1968). "2,3-Bis(perfluormethyl)bicyclo2.2.2]octa-2,5,7-trienes and their photorearrangement reactions". J.Am.Chem.Soc. 90 (1): 215–216. doi:10.1021/ja01003a041. Retrieved 10/19/2012.
{{cite journal}}: Check date values in:|accessdate=(help) - ^ Handbook of inorganic compounds. Boca Raton [u.a.]: CRC Press. 1995. p. 74. ISBN 0849386713.
{{cite book}}:|first=has generic name (help);|first=missing|last=(help) - ^ Henshaw, T. L. (1 April 1987). "Collisional decomposition of bromine azide". The Journal of Physical Chemistry. 91 (9): 2287–2293. doi:10.1021/j100293a016.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ "Bromine azide (Br(N3))(7CI,8CI,9CI)(CAS No. 13973-87-0)". Chemical Products. Guidechem. Retrieved 10 November 2012.