3,5-dibromopyrocatechol

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Structural formula
Structural formula of 3,5-dibromopyrocatechol
General
Surname 3,5-dibromopyrocatechol
other names
  • 3,5-dibromo-1,2-benzenediol ( IUPAC )
  • 3,5-dibromo-1,2-dihydroxybenzene
Molecular formula C 6 H 4 Br 2 O 2
External identifiers / databases
CAS number 111167-61-4
PubChem 3753114
ChemSpider 2982506
Wikidata Q223008
properties
Molar mass 267.9 g · mol -1
Physical state

firmly

Melting point

58-60  ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,5-Dibromopyrocatechol is a chemical compound that belongs to both the phenols and the halogen aromatic compounds . It is isomeric to 3,4-dibromopyrocatechol , 3,6-dibromopyrocatechol, and 4,5-dibromopyrocatechol .

presentation

3,5-dibromopyrocatechol can be produced by dakin oxidation from 3,5-dibromosalicylaldehyde , which in turn is synthesized by bromination of salicylaldehyde with elemental bromine in glacial acetic acid .

Production of 3,5-dibromopyrocatechol from salicylaldehyde

Reactions

Esterification with acetic anhydride gives the diacetate, the melting point of which is 96 ° C.

Esterification of 3,5-dibromopyrocatechol with acetic anhydride

3,5-Dibromo- o -benzoquinone is formed with silver oxide in THF .

Oxidation of 3,5-dibromopyrocatechol with silver oxide in THF

Analytical evidence

The bromination with potassium bromide and bromine produces tetrabromo-catechol , which has a melting point of 192 ° C.

Bromination of 3,6-dibromopyrocatechol

The 2-methyl ether is registered under the CAS number 79893-93-3, its melting point is 67–68 ° C.

Individual evidence

  1. ^ A b c Buckingham: Dictionary of organic compounds. Volume 9, p. 1914 ( limited preview in Google book search).
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ^ A b J. Paquet, P. Brassard: Reactions of polar dienes with o -quinones . In: Canadian Journal of Chemistry . 67 (8), 1989, pp. 1354-1358, doi : 10.1139 / v89-207 .
  4. ^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 331.
  5. ^ Association of authors: Organikum , 19th edition, Johann Ambrosius Barth, Leipzig · Berlin · Heidelberg 1993, ISBN 3-335-00343-8 , p. 653.