4-Bromoaniline

Last updated
4-Bromoaniline [1]
4-Bromoaniline.svg
4-bromoaniline-from-xtal-2003-3D-balls.png
Names
Preferred IUPAC name
4-Bromoaniline
Other names
  • (4-Bromophenyl)amine
  • p-Bromoaniline
  • 4-Bromobenzenamine
  • p-Bromophenylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.086 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-393-9
PubChem CID
RTECS number
  • BW9280000
UNII
UN number 2811
  • InChI=1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Yes check.svgY
    Key: WDFQBORIUYODSI-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
    Key: WDFQBORIUYODSI-UHFFFAOYAG
  • Brc1ccc(N)cc1
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:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

Preparation

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

Synthesized and purified p-bromoaniline Para-bromoanilina.jpg
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. [3]

Related Research Articles

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Werner Emmanuel Bachmann was an American chemist. Bachmann was born in Detroit, Michigan where he studied chemistry and chemical engineering at Wayne State University and later at the University of Michigan in Ann Arbor nearby. He completed his doctorate under Moses Gomberg and spent the rest of his academic career at the University of Michigan.

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References

  1. 4-Bromoaniline, Chemblink.com
  2. M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses .; Collective Volume, 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.