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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL57376 Y
ChemSpider	7519 Y
ECHA InfoCard	100.003.086
EC Number	203-393-9
PubChem CID	7807
RTECS number	BW9280000
UNII	0RR61TC330 N
UN number	2811
CompTox Dashboard (EPA)	DTXSID7021867
InChI InChI=1S/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Y Key: WDFQBORIUYODSI-UHFFFAOYSA-N Y 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). N verify (what is YN ?) 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]