3,5-dinitroanisole

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Structural formula
Structure of 3,5-dinitroanisole
General
Surname 3,5-dinitroanisole
other names
  • Dinitroanisole
  • 1-methoxy-3,5-dinitrobenzene
Molecular formula C 7 H 6 N 2 O 5
External identifiers / databases
CAS number 5327-44-6
PubChem 79231
ChemSpider 71556
Wikidata Q223021
properties
Molar mass 198.13 g mol −1
Physical state

firmly

Melting point

105 ° 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-Dinitroanisole is a solid with a melting point of 105 ° C. It is derived from both anisole  (methoxybenzene) and nitrobenzene or dinitrobenzenes . The structure consists of a benzene ring with a methoxy group  (-OCH 3 ) and two nitro groups  (-NO 2 ) as substituents .

presentation

3,5-Dinitroanisole is prepared by reacting 1,3,5-Trinitrobenzene with sodium methoxide in abs. Methanol .

Production of 3,5-dinitroanisole from 1,3,5-trinitrobenzene

Reactions

The nitration of 3,5-dinitroanisole with nitric acid and sulfuric acid leads to 2,3,5-trinitroanisole .

Nitration of 3,5-dinitroanisole

use

3,5-dinitroanisole is an intermediate in the preparation of an inhibitor of catechol- O used -methyl-transferase (COMT) 3,5-Dinitrobrenzcatechins .

Individual evidence

  1. a b Frederic Reverdin: 3,5-Dinitroanisole In: Organic Syntheses . 7, 1927, p. 28, doi : 10.15227 / orgsyn.007.0028 ; Coll. Vol. 1, 1941, p. 219 ( PDF ).
  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 M. H. Vermeulen: "Sur la structure des dinitranisols", in: Rec. Trav. Chim. , 1906 , 25 , pp. 12-31; Full text .
  4. a b M. H. Vermeulen: "Sur quelques trinitranisols", in: Rec. Trav. Chim. , 1912 , 31 , pp. 101-104; Full text .
  5. Data sheet 3,5-Dinitroanisol from Sigma-Aldrich , accessed on July 16, 2010 ( PDF ).Template: Sigma-Aldrich / name not given