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2,4,6-Tribromoaniline

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2,4,6-Tribromoaniline is a brominated derivative of aniline with the formula C6H4Br3N. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents.[1]

2,4,6-Tribromoaniline
The space-filling model of 2,4,6-tribromoaniline
The ball and stick model of 2,4,6-tribromoaniline
Names
Preferred IUPAC name
2,4,6-Tribromoaniline
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.183 Edit this at Wikidata
EC Number
  • 205-700-1
UNII
  • InChI=1S/C6H4Br3N/c7-3-1-4(8)6(10)5(9)2-3/h1-2H,10H2
    Key: GVPODVKBTHCGFU-UHFFFAOYSA-N
  • C1=C(C=C(C(=C1Br)N)Br)Br
Properties
C6H4Br3N
Molar mass 329.817 g·mol−1
Melting point 120 °C (248 °F; 393 K)
Boiling point 300 °C (572 °F; 573 K)
Insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful, Corrosive, Toxic
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H302, H311, H312, H315, H318, H319, H331, H332, H373
P260, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point Non-flammable
Non-flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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2,4,6-Tribromoaniline can be prepared by treating bromine water with aniline in a solution of acetic acid or dilute hydrochloric acid:[1]

 
By reacting bromine with aniline in water, a white precipitate immediately forms and that is 2,4,6-tribromoaniline

Reactions

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Diazotization, then reaction with ethanol to replace the diazonium group with hydrogen, gives 1,3,5-tribromobenzene.[2]

See also

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References

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  1. ^ a b "Synthesis of 2,4,6-tribromoaniline from aniline".
  2. ^ Coleman, G. H.; Talbot, William F. (1933). "sym.-Tribromobenzene". Organic Syntheses. 13: 96. doi:10.15227/orgsyn.013.0096.
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