4-Bromoaniline

4-Bromoaniline^[1]
Names
	Preferred IUPAC name 4-Bromoaniline
	Other names (4-Bromophenyl)amine; p-Bromoaniline; 4-Bromobenzenamine; p-Bromophenylamine;
Identifiers
CAS Number	106-40-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL57376 ;
ChemSpider	7519 ;
ECHA InfoCard	100.003.086
EC Number	203-393-9;
PubChem CID	7807;
RTECS number	BW9280000;
UNII	0RR61TC330 ;
UN number	2811
CompTox Dashboard (EPA)	DTXSID7021867 ;
	InChI InChI=1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Key: WDFQBORIUYODSI-UHFFFAOYSA-N ; InChI=1/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Key: WDFQBORIUYODSI-UHFFFAOYAG;
	SMILES Brc1ccc(N)cc1;
Properties
Chemical formula	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)
Solubility in water	<0.1 g/100 mL at 23 °C
Magnetic susceptibility (χ)	-84.06·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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

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]

References

^ 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.

[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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