1,2,3-triazole

Structural formula
General
Surname	1,2,3-triazole
other names	1 H -1,2,3-triazole; Osotriazole;
Molecular formula	C 2 H 3 N 3
Brief description	colorless liquid (from 25 ° C)
External identifiers / databases
EC number	608-262-3
ECHA InfoCard	100.128.405
PubChem	67516
Wikidata	Q161297
properties
Molar mass	69.07 g mol −1
Physical state	liquid
density	1.192 g cm −3 (25 ° C)
Melting point	23-25 ° C
boiling point	203 ° C (1003 hPa)
solubility	soluble in water
Refractive index	1.4854 (25 ° C)
safety instructions
GHS labeling of hazardous substances 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 . Refractive index: Na-D line , 20 ° C

1,2,3-Triazole is a chemical compound from the group of the triazoles and isomeric to 1,2,4-Triazole .

Extraction and presentation

1,2,3-Triazole can be obtained by Huisgen azide-alkyne 1,3-dipolar cycloaddition , copper (CuAAC) or ruthenium (RuAAC) catalyzed azide-alkyne cycloaddition .

properties

1,2,3-triazole is a colorless liquid with a pK _s value of 1.17 weak base is. Two tautomers can occur with the 1 H and 2 H forms . In solution, the 2 H form dominates in most solvents .

The compound can decompose strongly exothermic. A thermoanalytical investigation showed a decomposition reaction with a very high heat of reaction of −2600 kJ / kg (−180 kJ / mol) from 200 ° C. Despite the high heat of decomposition, the connection is not explosive in terms of the Explosives Act , as no positive result was observed either in the BAM 50/60 steel pipe test or in the Koenen test with a 2 mm hole diameter. The Koenentest with 1 mm hole diameter is positive.

use

1,2,3-Triazole is used in research as a building block for more complex chemical compounds, such as B. used the active ingredient tazobactam .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet 1,2,3-triazole from Sigma-Aldrich , accessed on March 5, 2011 ( PDF ).
↑ Entry on 1,2,3-1H-triazoles at ChemBlink , accessed on March 5, 2011.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-488.
↑ Organic Chemistry Portal: Synthesis of 1,2,3-triazoles and benzotriazoles
^ Theophil Eicher, Siegfried Hauptmann, Andreas Speicher: The chemistry of heterocycles: structure, reactions, syntheses, and applications , Chapter: 123-Triazole, p. 201; ISBN 978-3-5273-0720-3 ( limited preview in Google Book Search).
↑ ^a ^b ^c ^d M. Malow, KD Wehrstedt, S. Neuenfeld: On the explosive properties of 1H-benzotriazole and 1H-1,2,3-triazole . Tetrahedron Letters 48 (2007), 1233-1235, doi : 10.1016 / j.tetlet.2006.12.046 .

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet 1,2,3-triazole from Sigma-Aldrich , accessed on March 5, 2011 ( PDF ).

[2] Entry on 1,2,3-1H-triazoles at ChemBlink , accessed on March 5, 2011.

[CRC90_3_488-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-488.

[4] Organic Chemistry Portal: Synthesis of 1,2,3-triazoles and benzotriazoles

[5] Theophil Eicher, Siegfried Hauptmann, Andreas Speicher: The chemistry of heterocycles: structure, reactions, syntheses, and applications , Chapter: 123-Triazole, p. 201; ISBN 978-3-5273-0720-3 ( limited preview in Google Book Search).

[Malow_et_al.-6] M. Malow, KD Wehrstedt, S. Neuenfeld: On the explosive properties of 1H-benzotriazole and 1H-1,2,3-triazole . Tetrahedron Letters 48 (2007), 1233-1235, doi : 10.1016 / j.tetlet.2006.12.046 .