Tetrabromohydroquinone

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Structural formula
Structural formula of tetrabromohydroquinone
General
Surname Tetrabromohydroquinone
other names
  • 2,3,5,6-tetrabromo-1,4-dihydroxybenzene
  • 2,3,5,6-tetrabromo-1,4-benzenediol
  • Bromhydranil
Molecular formula C 6 H 2 Br 4 O 2
Brief description

gray powder

External identifiers / databases
CAS number 2641-89-6
EC number 220-142-9
ECHA InfoCard 100.018.312
PubChem 75480
ChemSpider 68349
Wikidata Q1402834
properties
Molar mass 425.89 g · mol -1
Physical state

firmly

Melting point
  • 252-255 ° C
  • 244 ° C
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetrabromohydroquinone is a gray solid that belongs to the group of polyphenols as well as the group of halogen aromatic compounds . The flash point of tetrabromohydroquinone is above 110 ° C.

Occurrence

Tetrabromohydroquinone is found in the gill loach Ptychodera flava and, along with riboflavin, is responsible for its bioluminescence .

presentation

Tetrabromohydroquinone can be obtained by bromination of 1,4-benzoquinone with elemental bromine in glacial acetic acid.

Production of tetrabromohydroquinone by bromination of quinone

Synthesis is also possible by introducing sulfur dioxide into an ethanolic solution of bromanil :

Production of tetrabromohydroquinone by reducing bromanil

properties

Tetrabromohydroquinone crystallizes in the monoclinic crystal system in the space group P 2 1 / n (space group no. 14, position 2) with the lattice parameters a = 889.07  pm , b = 473.16 pm, c = 1106.12 pm and β = 92.167 °. In the unit cell are 2  formula units . Template: room group / 14.2

Individual evidence

  1. a b sheet tetrabromohydroquinone from Acros, accessed on 20 February 2010 .
  2. a b c data sheet tetrabromohydroquinone from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
  3. VVRichter: chemistry of carbon compounds .
  4. ^ A b c Eduard Sarauw: Investigations into benzoquinone and some derivatives of the same , quarterly journal of the Natural Research Society in Zurich, 1881.
  5. Tetrabromohydroquinone and riboflavin are possibly responsible for green luminescence in the luminous acorn worm, Ptychodera flava; PMID 15966053 .
  6. VR Thalladi, H.-C. Weiss, R. Boese, A. Nangia, G. Desiraju: "A comparative study of the crystal structure of tetrahalogenated hydroquinones and γ-hydroquinone", in: Acta Cryst. , 1999 , B55 , pp. 1005-1013. Full text  ( page no longer available , search in web archivesInfo: The link was automatically marked as defective. Please check the link according to the instructions and then remove this notice.@1@ 2Template: Dead Link / www.soton.ac.uk