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	172.02 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
Safety data sheet	External MSDS
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H311, H315, H319, H332, H335, H373
GHS precautionary statements	P260, P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P305+351+338, P312, P314, P321, P322, P330, P332+313, P337+313, P361, P362, P363, P403+233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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 p-bromobiphenyl via the Gomberg-Bachmann reaction.[2]

Synthesised and purified p-Bromoaniline

Synthesis

4-bromoaniline can be made by reacting aniline with bromine with a protection with acetyl chloride.

Applications

In the synthesis of Bromamid.[3]
In the synthesis of Dibromsalan (Disanyl).

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References

4-Bromoaniline, Chemblink.com
M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses.; Collective Volume, 1, p. 113
Takamura, K; Shioya, A; Minamoto, K; Asada, N; Takaku, S; Yoshimitsu, A; Nitta, Y. "Studies on analgesics of aniline series. I. Preparation and properties of beta-alaninamide series". Chem Pharm Bull. 13: 198–204. PMID 5863464.

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[1] 4-Bromoaniline, Chemblink.com

[2] M. Gomberg and W. E. Bachmann (1941). "p-Bromobiphenyl". Organic Syntheses.; Collective Volume, 1, p. 113

[3] Takamura, K; Shioya, A; Minamoto, K; Asada, N; Takaku, S; Yoshimitsu, A; Nitta, Y. "Studies on analgesics of aniline series. I. Preparation and properties of beta-alaninamide series". Chem Pharm Bull. 13: 198–204. PMID 5863464.