Trinitroethylorthoformate

Trinitroethylorthoformate
Names
	Preferred IUPAC name 2-[Bis(2,2,2-trinitroethoxy)methoxy]-1,1,1-trinitroethane
	Other names TNEOF;
Identifiers
CAS Number	14548-59-5;
3D model (JSmol)	Interactive image;
ChemSpider	123273;
PubChem CID	139780;
CompTox Dashboard (EPA)	DTXSID80932613 ;
	InChI InChI=1S/C7H7N9O21/c17-8(18)5(9(19)20,10(21)22)1-35-4(36-2-6(11(23)24,12(25)26)13(27)28)37-3-7(14(29)30,15(31)32)16(33)34/h4H,1-3H2 Key: NWWHXKXUBVOXEX-UHFFFAOYSA-N;
	SMILES C(C([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OC(OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-];
Properties
Chemical formula	C7H7N9O21
Molar mass	553.174
Appearance	Colorless crystals
Melting point	128 °C (262 °F; 401 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trinitroethylorthoformate also known as TNEOF is an explosive with excellent chemical stability. It does not have hygroscopicity, does not dissolve in water, and does not react with acids. It decomposes in aqueous sodium hydroxide solution to release formaldehyde odor. The explosion point of TNEOF is 229 °C, though it begins to decompose at 190 °C. Its explosion heat is 6.3076 J/g and specific volume is 682 L/kg.^[1] Its structure is closely related to that of trinitroethylorthocarbonate (TNEOC). Both are highly explosive and very shock-sensitive, and may be dissolved in nitroalkanes to reduce their shock-sensitivity.^[1]

Synthesis

Trinitroethanol is reacted with chloroform under a catalyst of FeCl₃.

{\ce {{\overset {chloroform}{CHCl3}}+ {\overset {Trinitroethanol}{3HOCH2C(NO2)3}}->[{\ce {FeCl3}}] {TNEOF}+ 3HCl}}

References

^ ^a ^b Liu, Jiping (2015). Liquid Explosives. Springer. pp. 5, 6, 8, 136, 309. ISBN 9783662458471. Retrieved 26 March 2016.

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[Liquid_Explosives-1] Liu, Jiping (2015). Liquid Explosives. Springer. pp. 5, 6, 8, 136, 309. ISBN 9783662458471. Retrieved 26 March 2016.

[1]

Names

Preferred IUPAC name 2-[Bis(2,2,2-trinitroethoxy)methoxy]-1,1,1-trinitroethane
Other names TNEOF
Identifiers
CAS Number	14548-59-5
3D model (JSmol)	Interactive image
ChemSpider	123273
PubChem CID	139780
CompTox Dashboard (EPA)	DTXSID80932613
InChI InChI=1S/C7H7N9O21/c17-8(18)5(9(19)20,10(21)22)1-35-4(36-2-6(11(23)24,12(25)26)13(27)28)37-3-7(14(29)30,15(31)32)16(33)34/h4H,1-3H2 Key: NWWHXKXUBVOXEX-UHFFFAOYSA-N
SMILES C(C([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OC(OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-])OCC([N+](=O)[O-])([N+](=O)[O-])[N+](=O)[O-]
Properties
Chemical formula	C₇H₇N₉O₂₁
Molar mass	553.174
Appearance	Colorless crystals
Melting point	128 °C (262 °F; 401 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references