Tetrabromo-o-xylene

Chemical compound From Wikipedia, the free encyclopedia

α,α,α',α'-Tetrabromo-o-xylene is an organobromine compound with the formula C6H4(CHBr2)2. Three isomers of α,α,α',α'-Tetrabromoxylene exist, but the ortho derivative is most widely studied. It is an off-white solid. The compound is prepared by the photochemical reaction of o-xylene with elemental bromine:[1]

C6H4(CH3)2 + 4 Br2 → C6H4(CHBr2)2 + 4 HBr
Quick facts Names, Identifiers ...
Tetrabromo-o-xylene
Names
Preferred IUPAC name
1,2-Bis(dibromomethyl)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.873 Edit this at Wikidata
EC Number
  • 236-176-2
UNII
  • InChI=1S/C8H6Br4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,7-8H
    Key: LNAOKZKISWEZNY-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)C(Br)Br)C(Br)Br
Properties
C8H6Br4
Molar mass 421.752 g·mol−1
Appearance off white solid
Melting point 115–116 Â°C (239–241 Â°F; 388–389 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H314, H335, H400
P260, P264, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P391, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
Close

Reaction of α,α,α',α'-tetrabromo-o-xylene with sodium iodide affords α,α'-dibromo-o-xylylene, which can be trapped with dienophiles to give naphthylene. In the absence of trapping agents, the xylylene relaxes to α,α'-dibromobenzocyclobutane:[2]

C6H4(CHBr2)2 + 2 NaI → C6H4(=CHBr)2 + 2 NaBr + I2
C6H4(=CHBr)2 → C6H4(CHBr)2

Cycloadditions of these xylylenes provides a pathway to acenes.[3]

References

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