1,2,4-triazole

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Structural formula
Structural formula of 1,2,4-triazole
General
Surname 1,2,4-triazole
other names
  • 1 H -1,2,4-triazole ( IUPAC )
  • Pyrrodiazole
Molecular formula C 2 H 3 N 3
Brief description

flammable, colorless scales with a faint odor

External identifiers / databases
CAS number 288-88-0
EC number 206-022-9
ECHA InfoCard 100.005.476
PubChem 9257
Wikidata Q161300
properties
Molar mass 69.07 g mol −1
Physical state

firmly

density

1.15 g cm −3

Melting point

120 ° C

boiling point
  • 260 ° C
  • 150 ° C (27 hPa)
solubility

good in water (547 g l −1 at 22 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 08 - Dangerous to health

Caution

H and P phrases H: 302-319-361d
P: 280-305 + 351 + 338-308 + 313
Toxicological data

1750 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2,4-Triazole is a chemical compound from the group of triazoles . It is in the form of colorless scales.

Extraction and presentation

1,2,4-Triazole can be obtained by further nitration of imidazole or Einhorn-Brunner reaction or Pellizzari reaction .

properties

The heat of decomposition determined by DSC is −76 kJ mol −1 or −1100 kJ kg −1 .

use

1,2,4-Triazole is used as an additive in fertilizers and as an intermediate in the production of fungicides through an addition reaction with epoxides or other electrophilic compounds. Triazole derivatives such as nitrotriazolone or ANTA are used as new, insensitive explosives.

safety instructions

At high temperatures, 1,2,4-triazole decomposes, producing nitrogen oxides and causing an explosion (flash point 170 ° C, ignition temperature around 490 ° C). It is listed in Annex VI of Regulation (EC) No. 1272/2008 (CLP) as category 2 toxic to reproduction and its use in cosmetics is prohibited (Annex II of Regulation (EC) No. 1223/2009 on cosmetic products ).

In 2015, 1,2,4-triazole was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The causes for the uptake of 1,2,4-triazole were concerns about environmental exposure , high (aggregated) tonnage, other hazard- related concerns and widespread use as well as the dangers arising from a possible assignment to the group of CMR substances. The re-evaluation has been running since 2015 and is carried out by Belgium .

Derivatives

See also

Web links

Commons : 1,2,4-Triazole  - Collection of Images, Videos, and Audio Files

Individual evidence

  1. ↑ a b c d e f g h i Entry on 1,2,4-triazole in the GESTIS substance database of the IFA , accessed on June 27, 2018(JavaScript required) .
  2. ↑ Entry on 1,2,4-triazole in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  3. ^ Potts KT: The Chemistry of 1,2,4-Triazoles. . In: Chemical Reviews . 61, No. 2, 1961, pp. 87-127. doi : 10.1021 / cr60210a001 .
  4. ↑ Grewer, T .; Klais, O .: Exothermic decomposition - investigations of the characteristic material properties , VDI-Verlag, series "Humanisierung des Arbeitsleben", Volume 84, Düsseldorf 1988, ISBN 3-18-400855-X , p. 9.
  5. ↑ SKW nitrogenwerke Piesteritz GmbH: Alzon ( Memento from April 15, 2016 in the Internet Archive ) (PDF; 29 kB), accessed on January 23, 2016.
  6. ↑ Directory of carcinogenic, mutagenic or toxic substances for reproduction ( Memento of September 22, 2010 in the Internet Archive ).
  7. ↑ Regulation (EC) No. 1223/2009
  8. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 1,2,4-triazole , accessed on May 20, 2019.Template: CoRAP status / 2015
  9. ↑ External identifiers of or database links to epronaz : CAS number: 59026-08-3, PubChem : 181208 , ChemSpider : 157653 , Wikidata : Q27259510 .
  10. ↑ External identifiers or database links for flucarbazone : CAS number: 145026-88-6, PubChem : 3081367 , ChemSpider : 2338984 , Wikidata : Q27254728 .
  11. ↑ External identifiers of or database links to Triamiphos : CAS number: 1031-47-6, EC number: 620-368-1, ECHA InfoCard: 100.149.164 , GESTIS substance database : 510380 , PubChem : 13943 , ChemSpider : 13341 , Wikidata : Q7840032 .
  12. ↑ External identifiers or database links for guanazole : CAS number: 1455-77-2, EC number: 215-937-2, ECHA InfoCard: 100.014.489 , PubChem : 15078 , ChemSpider : 14350 , Wikidata : Q27145298 .
  13. ↑ External identifiers of or database links for 3-mercapto-1,2,4-triazole : CAS number: 3179-31-5, EC number: 221-656-6, ECHA InfoCard: 100.019.688 , PubChem : 2723802 , ChemSpider : 2005993 , Wikidata : Q27288291 .