Tetramethylammonium nitrate

Chemical compound From Wikipedia, the free encyclopedia

Tetramethylammonium nitrate is an organic compound with the chemical formula [N(CH3)4]NO3. It is a white crystalline solid. It is a quaternary ammonium salt. Tetramethylammonium nitrate consists of tetramethylammonium cations [N(CH3)4]+ and nitrate anions NO−3.

Quick facts Names, Identifiers ...
Tetramethylammonium nitrate
Tetramethylazanium nitrate
Names
IUPAC name
Tetramethylazanium nitrate[1]
Other names
Methanaminium, N,N,N-trimethyl-, nitrate (1:1)[1]
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 217-723-4
  • InChI=1S/C4H12N.NO3/c1-5(2,3)4;2-1(3)4/h1-4H3;/q+1;-1
    Key: QGPVYHSXZFOSRL-UHFFFAOYSA-N
  • C[N+](C)(C)C.[N+](=O)([O-])[O-]
Properties
[N(CH3)4]NO3
Molar mass 136.151 g·mol−1
Appearance White crystalline solid[1][2]
Odor Odorless[1]
Melting point 300 °C (572 °F; 573 K)[2]
0.1 g/mL[2]
Hazards
GHS labelling:
GHS03: OxidizingGHS07: Exclamation mark
Danger
H272, H315, H319, H335
P210, P220, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
2
1
1
OX
Related compounds
Related compounds
 Tetramethylammonium chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses

Tetramethylammonium nitrate is used as a glycolate oxidase inhibitor.[2]

It is also used, together with trifluoromethanesulfonic anhydride, to selectively and rapidly nitrate cyclic (number of atoms in the ring is 5 or 6), aromatic and heteroaromatic compounds in dichloromethane as a solvent. An advantage is the removal of undesired byproducts. This very mild nitration is used for large-scale syntheses and gives high product yields that often require no further purification.[3]

Reactions

At high temperatures, tetramethylammonium nitrate decomposes to trimethylamine and methyl nitrate.[4]

[N(CH3)4]NO3 → N(CH3)3 + CH3NO3

References

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