2,4,6-trinitro- m- cresol

Structural formula
General
Surname	2,4,6-trinitro- m- cresol
other names	3-methyl-2,4,6-trinitrophenol ( IUPAC ) Methyl picric acid
Molecular formula	C 7 H 5 N 3 O 7
Brief description	yellow needles
External identifiers / databases
CAS number 602-99-3 EC number 210-027-1 ECHA InfoCard 100.009.116 PubChem 11772 ChemSpider 11279 Wikidata Q19833924
properties
Molar mass	243.13 g mol −1
Physical state	firmly
density	1.75 g cm −3
Melting point	110 ° C
solubility	Easily soluble in alcohol, ether and acetone poorly soluble in water
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 201-332-312-302 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,4,6-Trinitro- m -cresol is an organic compound which is derived from 1,3,5-trinitrobenzene as well as from m-cresol . As a multi-nitrated aromatic, the substance has explosive properties.

Extraction and presentation

2,4,6-trinitro- m -cresol can be prepared by nitration of m- cresol disulfonic acid, which in turn can be produced by sulfonation of m-cresol .

properties

2,4,6-trinitro- m -cresol is a crystalline solid. As a phenol derivative with electron-withdrawing substituents, the substance acts as an acid. The pK _a is 3.73. The solubilities in different solvents differ greatly. The rather moderate solubility in chlorinated hydrocarbons and ethers is offset by complete miscibility with acetone or ethyl acetate.

Solubility in various solvents (in g per 100 g of solvent)
solvent	Methanol	Ethanol	Diethyl ether	acetone	Ethyl acetate	benzene	toluene	chloroform	Carbon tetrachloride
at 17 ° C	11.77	6.17	4.42	94.81	37.27	13.50	14.40	3.57	0.17
at 50 ° C	43.15	18.53	6.81 (34 ° C)	197.43	76.52	56.10	47.50	15.67	1.08

The connection is particularly explosive when dry due to impact, friction, heat and other ignition sources and is subject to the Explosives Act .

Table with important explosion-relevant properties:

Oxygen balance	−62.52%
Nitrogen content	17.95%
Normal gas volume	996 l kg −1
Explosion heat	3310 kJ kg −1 (H 2 O (l)) 3196 kJ kg −1 (H 2 O (g))
Specific energy	857 kJ kg −1 (87.4 mt / kg)
Lead block bulge	28.5 cm 3 g −1
Detonation velocity	6850 m s −1
Deflagration point	150 ° C
Sensitivity to impact	12 Nm

use

A mixture of 60% trinitrocresol and 40% picric acid was used as a garnet filling during World War I, as this mixture is already liquid from 85 ° C.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l m n} Köhler, J .; Meyer, R .; Homburg, A .: Explosivstoffe , tenth, completely revised edition, Wiley-VCH, Weinheim 2008, p. 333, ISBN 978-3-527-32009-7 .
2. ↑ ^{a b} Entry on 2,4,6-trinitro-m-cresol in the GESTIS substance database of the IFA , accessed on July 28, 2015(JavaScript required) .
3. ^ Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals: Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 142 ( limited preview in Google Book search).
4. ↑ ^{a b} Sasaki, M .; Nodera, K .; Mukai, K .; Yoshioka, H .: Studies on the Nitration of m-Cresol. A New Selective Method for the Preparation of 3-Methyl-6-Nitrophenol in Bull. Chem. Soc. Yep 50 (1977) 276-279, doi : 10.1246 / bcsj.50.276 .
5. ↑ Entry on 2,4,6-trinitro-m-cresol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ ^{a b} Desvergnes: in Chem. Zentralblatt 100, II (1929) 1790.
7. ↑ Roth, L .; Weller, U .: Hazardous Chemical Reactions , 65th supplement, ecomed-Verlag 2011.
8. ↑ Explosives Act, Appendix I, List of Explosive Substances ( BGBl. 1975 I p. 853 ), to which the law is to be applied in full.