Trinitrophloroglucinol

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Trinitrophloroglucinol
Names
IUPAC name
2,4,6-Trinitrobenzene-1,3,5-triol
Other names
1,3,5-Trihydroxy-2,4,6-trinitrobenzene
2,4,6-Trinitro-1,3,5-benzenetriol
2,4,6-Trinitro-1,3,5-trihydroxybenzene
2,4,6-Trinitro-1,3,5-trihydroxy-benzol
TNPG
Trinitro-phloroglucinol
Properties
C6H3N3O9
Molar mass 261.105 g/mol
Appearance Yellowish solid
Odor Odorless
Density 1.89 g/cm3[1]
Melting point 167–168 °C (333–334 °F; 440–441 K) [2]
Boiling point Decomposes
Soluble
Solubility Soluble in dimethylformamide, ethanol
Vapor pressure ~0 mmHg
Hazards
Safety data sheet None
Related compounds
Related compounds
Picric acid
Styphnic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Trinitrophloroglucinol (TNPG) or 2,4,6-trinitro-1,3,5-benzenetriol is a nitrated aromatic phenol, used as high explosive. It has the chemical formula C6H3N3O9.

Properties

Chemical

Addition of trinitrophloroglucinol to an aq. solution of ferric chloride gives a blue-violet product.

Potassium bicarbonate mixed with TNPG gives its tripotassium salt.

Physical

Trinitrophloroglucinol is a yellowish or yellow-orange solid. It is soluble in water and organic solvents.

Explosive

There is little available data about TNGU's explosive properties. Some sources indicate that it's somewhat sensitive.

Potassium salts of TNPG have been found to be more stable than its parent compound.[3]

Availability

TNPG is not available to the public and when available it's more expensive than similar explosive compounds.

Preparation

Trinitrophloroglucinol can be prepared via complete nitration of phloroglucinol. The reaction temperature is maintained between 5-10 °C. Yield is given as 91%.[4][5]

Refluxing hexanitrobenzene with hydrofluoric acid at 90 °C for 2 hours will produce TNPG, with an yield of 40%.[6]

Projects

  • Make blasting caps
  • Make colored compounds

Handling

Safety

Trinitrophloroglucinol is toxic and a powerful explosive. Handle it with care.

Storage

In closed containers.

Disposal

Should be carefully incinerated or neutralized with an oxidizing solution.

References

  1. Wolff; Gredel; Irngartinger; Dreier; Acta Crystallographica, Section C: Crystal Structure Communications; vol. 52; nb. pt 12; (1996); p. 3225 - 3227
  2. Cantillo, David; Damm, Markus; Dallinger, Doris; Bauser, Marcus; Berger, Markus; Kappe, C. Oliver; Organic Process Research and Development; vol. 18; nb. 11; (2014); p. 1360 - 1366
  3. https://www.sciencedirect.com/science/article/abs/pii/S0304389407001161?via%3Dihub
  4. Straessler, Nicholas A.; Synthetic Communications; vol. 40; nb. 17; (2010); p. 2513 - 2519
  5. https://patents.google.com/patent/US7737308B1/en
  6. Nielsen, Arnold T.; Chafin, Andrew P.; Christian, Stephen L.; Journal of Organic Chemistry; vol. 49; nb. 24; (1984); p. 4575 - 4580

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