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4-Bromoaniline

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4-Bromoaniline
Names
Preferred IUPAC name 4-Bromoaniline
Other names
  • (4-Bromophenyl)amine
  • p-Bromoaniline
  • 4-Bromobenzenamine
  • p-Bromophenylamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.086 Edit this at Wikidata
EC Number
  • 203-393-9
PubChem CID
RTECS number
  • BW9280000
UNII
UN number 2811
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2Key: WDFQBORIUYODSI-UHFFFAOYSA-N
  • InChI=1/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2Key: WDFQBORIUYODSI-UHFFFAOYAG
SMILES
  • Brc1ccc(N)cc1
Properties
Chemical formula C6H6BrN
Molar mass 172.025 g·mol
Density 1.5 g/cm
Melting point 60 to 64 °C (140 to 147 °F; 333 to 337 K)
Solubility in water <0.1 g/100 mL at 23 °C
Magnetic susceptibility (χ) -84.06·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H302, H311, H315, H319, H332, H335, H373
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

4-Bromoaniline can be made by reacting acetyl chloride-protected aniline with bromine.

Synthesized and purified p-bromoaniline

Reactions

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.

References

  1. 4-Bromoaniline, Chemblink.com
  2. M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses; Collected Volumes, vol. 1, p. 113.
  3. 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.
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