4-Bromoaniline
Appearance
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Names | |||
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Preferred IUPAC name
4-Bromoaniline | |||
Other names
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Identifiers | |||
3D model (JSmol)
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ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.003.086 | ||
EC Number |
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PubChem CID
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RTECS number |
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UNII | |||
UN number | 2811 | ||
CompTox Dashboard (EPA)
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Properties | |||
C6H6BrN | |||
Molar mass | 172.025 g·mol−1 | ||
Density | 1.5 g/cm3 | ||
Melting point | 60 to 64 °C (140 to 147 °F; 333 to 337 K) | ||
<0.1 g/100 mL at 23 °C | |||
-84.06·10−6 cm3/mol | |||
Hazards | |||
GHS labelling: | |||
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Danger | |||
H302, H311, H315, H319, H332, H335, H373 | |||
P260, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501 | |||
Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Bromoaniline is a compound where an aniline molecule is substituted with a bromine atom on the para position. Commercially available, this compound may be used as a building block, e.g. in the preparation of monobrominated biphenyl via the Gomberg-Bachmann reaction.[2]
Preparation
[edit]4-Bromoaniline can be made by reacting acetyl chloride-protected aniline with bromine.
![](http://upload.wikimedia.org/wikipedia/commons/thumb/5/5b/Para-bromoanilina.jpg/220px-Para-bromoanilina.jpg)
Reactions
[edit]One laboratory route to 1-bromo-4-iodobenzene involves the Sandmeyer reaction. 4-Bromoaniline is treated with concentrated sulfuric acid and sodium nitrite, then potassium iodide.[3]
References
[edit]- ^ 4-Bromoaniline, Chemblink.com
- ^ M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses; Collected Volumes, vol. 1, p. 113.
- ^ Banerjee, M.; Shukla, R.; Rathore, R. (15 January 2009). "Synthesis, Optical, and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires". Journal of the American Chemical Society. 131 (5): 1780–1786. doi:10.1021/ja805102d. PMID 19146375.