3,5-dinitro catechol

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Structural formula
Structural formula of 3,5-dinitrocatechol
General
Surname 3,5-dinitro catechol
other names
  • 3,5-dinitro-1,2-dihydroxybenzene
  • 3,5-dinitro-1,2-benzenediol
Molecular formula C 6 H 4 N 2 O 6
Brief description

yellow solid

External identifiers / databases
CAS number 7659-29-2
PubChem 3870203
ChemSpider 3094995
DrugBank DB02105
Wikidata Q223026
properties
Molar mass 200.11 g · mol -1
Physical state

firmly

Melting point

164 ° C

pK s value
  • pK s 1 = 3.39
  • pK s 2 = 10.03
solubility
  • in water 17 g l −1
  • soluble in ethanol
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,5-Dinitrocatechol is a chemical compound that belongs to both the phenols and the nitroaromatics group.

presentation

One synthesis route for 3,5-dinitrocatechol 5 starts from 1,3,5-trinitrobenzene 1 , which reacts with sodium methoxide in methanol to form 3,5-dinitroanisole 2 . This is then nitrated with nitric acid and sulfuric acid. The resulting 2,3,5-trinitroanisole 3 is converted again to 3,5-dinitroveratrol 4 with sodium methoxide . Ether cleavage then yields the end product 5 .

Production of 3,5-dinitrocatechol

Derivatives

The methylation of 3,5-dinitropyrocatechol leads to different ethers, the melting points of which are listed in the table below.

Complete methylation of 3,4-dinitrocatechol with dimethyl sulfate
Methyl ether of 3,5-dinitrocatechol
Structural formula 4,6-dinitroguaiacol 3,5-dinitroguaiacol 3,5-dinitroveratrol
Common name 4,6-dinitroguaiacol 3,5-dinitroguaiacol 3,5-dinitroveratrol
CAS number 63975-57-5 13661-34-2
molar mass 214.1 214.1 228.1
Melting point 80 ° C 123 ° C 102 ° C

The esterification with acetic anhydride produces the diacetate, which has a melting point of 112 ° C.

Esterification of 3,4-dinitrocatechol with acetic anhydride

use

3,5-dinitrocatechol is used as an inhibitor of catechol-O-methyl-transferase (COMT). It is also used for the photometric determination of niobium , titanium (element) , vanadium , tungsten and rare earths.

Individual evidence

  1. ↑ a b c d e f data sheet 3,5-dinitrocatechol, solid from Sigma-Aldrich , accessed on December 26, 2019 ( PDF ).
  2. ^ A b c d e f J. Buckingham: "Dictionary of organic compounds", Volume 9, p. 2767. ( limited preview in Google book search).
  3. ^ MH Vermeulen: "Sur la structure des dinitranisols", in: Rec. Trav. Chim. , 1906 , 25 , pp. 12-31; Full text .
  4. ^ MH Vermeulen: "Sur quelques trinitranisols", in: Rec. Trav. Chim. , 1912 , 31 , pp. 101-104; Full text .