Mellitic anhydride

Names
Preferred IUPAC name

Benzo[1,2-c:3,4-c′:5,6-c′′]trifuran-1,3,4,6,7,9-hexone

Identifiers

CAS Number

* 4253-24-1 N

3D model (JSmol)

* Interactive image

ChemSpider |

* 223826 N

PubChem CID

* 255291

UNII |

* R2K7PH4G2C Y

InChI

* InChI=1S/C12O9/c13-7-1-2(8(14)19-7)4-6(12(18)21-11(4)17)5-3(1)9(15)20-10(5)16 N

Key: NNYHMCFMPHPHOQ-UHFFFAOYSA-N N

* InChI=1/C12O9/c13-7-1-2(8(14)19-7)4-6(12(18)21-11(4)17)5-3(1)9(15)20-10(5)16

Key: NNYHMCFMPHPHOQ-UHFFFAOYAV

SMILES

* O=C2OC(=O)c1c4c(c3c(c12)C(=O)OC3=O)C(=O)OC4=O

Properties

Chemical formula

| C12O9
Molar mass | 288.123 g·mol−1
Appearance  | colorless solid[1]
Melting point |  161 °C; 322 °F; 434 K[1]
Vapor pressure | 0.000004 mmHg (20°C)[1]
Hazards
NIOSH (US health exposure limits):

PEL (Permissible)

| none[1]

REL (Recommended)

| TWA 0.005 ppm (0.04 mg/m3) Should be handled in the workplace as an extremely toxic substance.[1]

IDLH (Immediate danger)

| N.D.[1]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Mellitic anhydride, the anhydride of mellitic acid, is an organic compound with the formula C12O9.

Containing no other elements (e.g., hydrogen) besides carbon and oxygen, mellitic anhydride is an oxide of carbon (oxocarbon), and, along with CO2, CO, and C3O2, is one of the only four that are reasonably stable under standard conditions. It is a white sublimable solid, apparently obtained by Justus Liebig and Friedrich Wöhler in 1830 in their study of mellite ("honey stone") and has the empirical formula C4O3.[2][3][4] The substance was properly characterized in 1913 by H. Meyer and K. Steiner.[5][6] It retains the aromatic character of the benzene ring.[7][8]

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 NIOSH Pocket Guide to Chemical Hazards. "#0635". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0635.html.
2. ↑ Wöhler, F. (1826). "Ueber die Honigsteinsäure". Annalen der Physik und Chemie 83 (7): 325–334. doi:10.1002/andp.18260830706. Bibcode: 1826AnP....83..325W. https://zenodo.org/record/1423510/files/article.pdf.
3. ↑ Liebig, J.; Wöhler, F. (1830). "Ueber die Zusammensetzung der Honigsteinsäure". Annalen der Physik und Chemie 94 (2): 161–164. doi:10.1002/andp.18300940202. Bibcode: 1830AnP....94..161L. https://zenodo.org/record/1423532/files/article.pdf.
4. ↑ Erdmann, O. L.; Marchand, R. F. (1848). "Ueber die Mellithsäure". Journal für Praktische Chemie 43 (2/3): 129–144. doi:10.1002/prac.18480430113. https://zenodo.org/records/1427804/files/article.pdf.
5. ↑ Meyer, H.; Steiner, K. (1913). "Über ein neues Kohlenoxyd C12O9". Berichte der Deutschen Chemischen Gesellschaft 46 (1): 813–815. doi:10.1002/cber.191304601105. https://zenodo.org/record/1426491.
6. ↑ Bugge, G. (1914). "Chemie: Ein neues Kohlenoxyd". Naturwissenschaftliche Wochenschrift 13/29 (12): 188. https://archive.org/stream/naturwissenschaf29deut#page/188/mode/1up.
7. ↑ Fowler, P. W.; Lillington, M. (2007). "Mellitic Trianhydride, C12O9: The Aromatic Oxide of Carbon". Journal of Chemical Information and Modeling 47 (3): 905–908. doi:10.1021/ci600547n. PMID 17315989.
8. ↑ Ermer, O.; Neudörfl, J. (2000). "Structure of Mellitic Trianhydride". Helvetica Chimica Acta 83 (1): 300–309. doi:10.1002/(SICI)1522-2675(20000119)83:1<300::AID-HLCA300>3.0.CO;2-L.

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Oxocarbons

Common oxides|

* CO
* CO2

Exotic oxides|

* CO3
* CO4
* CO5
* CO6
* C2O
* C2O2
* C2O3
* C2O4 (1,2-Dioxetanedione and 1,3-Dioxetanedione)
* C3O
* C3O2
* C3O3
* C3O6
* C4O2
* C4O4
* C4O6
* C5O2
* C5O5
* C6O6 (Cyclohexanehexone and Ethylenetetracarboxylic dianhydride)
* C8O8
* C9O9
* C10O8
* C10O10
* C12O6
* C12O9
* C12O12

Polymers|

* Graphite oxide
* C3O2
* CO
* CO2

Compounds derived from oxides|

* Metal carbonyls
* Carbonic acid
* Bicarbonates
* Carbonates
* Dicarbonates
* Tricarbonates

* v
* t
* e

Oxides

Mixed oxidation states|

* Antimony tetroxide (Sb2O4)
* Cobalt(II,III) oxide (Co3O4)
* Europium(II,III) oxide (Eu3O4)
* Iron(II,III) oxide (Fe<sub>3O4)
* Lead(II,IV) oxide (Pb3O4)
* Manganese(II,III) oxide (Mn3O4)
* Silver(I,III) oxide (Ag2O2)
* Triuranium octoxide (U3O8)
* Carbon suboxide (C3O2)
* Mellitic anhydride (C12O9)
* [[Chemistry:Praseodymium(III,IV) Praseodymium(III,IV) oxide]] (Pr6O11)
* Terbium(III,IV) oxide (Tb4O7)

+1 oxidation state|

* Copper(I) oxide (Cu<sub>2O)
* Caesium oxide (Cs2O)
* Dicarbon monoxide (C2O)
* Dichlorine monoxide (Cl2O)
* Gallium(I) oxide (Ga2O)
* Lithium oxide (Li2O)
* Potassium oxide (K2O)
* Rubidium oxide (Rb2O)
* Silver oxide (Ag2O)
* Thallium(I) oxide (Tl2O)
* Sodium oxide (Na2O)
* Water (hydrogen oxide) (H2O)

+2 oxidation state|

* Aluminium(II) oxide (AlO)
* Barium oxide (BaO)
* Beryllium oxide (BeO)
* Cadmium oxide (CdO)
* Calcium oxide (CaO)
* Carbon monoxide (CO)
* Chromium(II) oxide (CrO)
* Cobalt(II) oxide (CoO)
* Copper(II) oxide (CuO)
* Europium(II) oxide (EuO)
* Germanium monoxide (GeO))
* Iron(II) oxide (FeO)
* Lead(II) oxide (PbO)
* Magnesium oxide (MgO)
* Manganese(II) oxide (MnO)
* Mercury(II) oxide (HgO)
* Nickel(II) oxide (NiO)
* Nitric oxide (NO)
* Palladium(II) oxide (PdO)
* Silicon monoxide (SiO)
* Strontium oxide (SrO)
* Sulfur monoxide (SO)
* Disulfur dioxide (S2O2)
* Thorium monoxide (ThO)
* Tin(II) oxide (SnO)
* Titanium(II) oxide (TiO)
* Vanadium(II) oxide (VO)
* Zinc oxide (ZnO)

+3 oxidation state|

* Aluminium oxide (Al<sub>2O3)
* Antimony trioxide (Sb2O3)
* Arsenic trioxide (As2O3)
* Bismuth(III) oxide (Bi2O3)
* Boron trioxide (B2O3)
* Cerium(III) oxide (Ce2O3)
* Dibromine trioxide (Br2O3)
* Chromium(III) oxide (Cr2O3)
* Dinitrogen trioxide (N2O3)
* Dysprosium(III) oxide (Dy2O3)
* Erbium(III) oxide (Er2O3)
* Europium(III) oxide (Eu2O3)
* Gadolinium(III) oxide (Gd2O3)
* Gallium(III) oxide (Ga2O3)
* Holmium(III) oxide (Ho2O3)
* Indium(III) oxide (In<sub>2O3)
* Iron(III) oxide (Fe2O3)
* Lanthanum oxide (La2O3)
* Lutetium(III) oxide (Lu2O3)
* Manganese(III) oxide (Mn2O3)
* Neodymium(III) oxide (Nd2O3)
* Nickel(III) oxide (Ni2O3)
* Phosphorus trioxide (P4O6)
* Praseodymium(III) oxide (Pr2O3)
* Promethium(III) oxide (Pm2O3)
* Rhodium(III) oxide (Rh2O3)
* [[Chemistry:Samarium(III) Samarium(III) oxide]] (Sm2O3)
* Scandium oxide (Sc2O3)
* Terbium(III) oxide (Tb2O3)
* Thallium(III) oxide (Tl2O3)
* Thulium(III) oxide (Tm2O3)
* Titanium(III) oxide (Ti2O3)
* Tungsten(III) oxide (W2O3)
* Vanadium(III) oxide (V2O3)
* Ytterbium(III) oxide (Yb2O3)
* Yttrium(III) oxide (Y2O3)

+4 oxidation state|

* Americium dioxide (AmO2)
* Carbon dioxide (CO2)
* Carbon trioxide (CO3)
* Cerium(IV) oxide (CeO2)
* Chlorine dioxide (ClO2)
* Chromium(IV) oxide (CrO<sub>2)
* Dinitrogen tetroxide (N2O4)
* Germanium dioxide (GeO<sub>2)
* [[Chemistry:Hafnium(IV) Hafnium(IV) oxide]] (HfO2)
* Lead dioxide (PbO2)
* Manganese dioxide (MnO2)
* Neptunium(IV) oxide (NpO2)
* Nitrogen dioxide (NO2)
* Osmium dioxide (OsO2)
* Plutonium(IV) oxide (PuO2)
* Praseodymium(IV) oxide (PrO2)
* Protactinium(IV) oxide (PaO2)
* Rhodium(IV) oxide (RhO2)
* Ruthenium(IV) oxide (RuO<sub>2)
* Selenium dioxide (SeO2)
* Silicon dioxide (SiO2)
* Sulfur dioxide (SO2)
* Tellurium dioxide (TeO<sub>2)
* [[Chemistry:Terbium(IV) Terbium(IV) oxide]] (TbO2)
* Thorium dioxide (ThO2)
* Tin dioxide (SnO2)
* Titanium dioxide (TiO<sub>2)
* Tungsten(IV) oxide (WO2)
* Uranium dioxide (UO2)
* Vanadium(IV) oxide (VO2)
* Zirconium dioxide (ZrO2)

+5 oxidation state|

* Antimony pentoxide (Sb2O5)
* Arsenic pentoxide (As2O5)
* Dinitrogen pentoxide (N2O5)
* Niobium pentoxide (Nb2O5)
* Phosphorus pentoxide (P2O5)
* Protactinium(V) oxide (Pa2O5)
* Tantalum pentoxide (Ta2O5)
* Vanadium(V) oxide (V2O5)

+6 oxidation state|

* Chromium trioxide (CrO3)
* Molybdenum trioxide (MoO3)
* Rhenium trioxide (ReO3)
* Selenium trioxide (SeO3)
* Sulfur trioxide (SO3)
* Tellurium trioxide (TeO3)
* Tungsten trioxide (WO3)
* Uranium trioxide (UO3)
* Xenon trioxide (XeO3)
* Iridium trioxide (IrO3)

+7 oxidation state|

* Dichlorine heptoxide (Cl2O7)
* Manganese heptoxide (Mn2O7)
* [[Chemistry:Rhenium(VII) Rhenium(VII) oxide]] (Re2O7)
* Technetium(VII) oxide (Tc2O7)

+8 oxidation state|

* Osmium tetroxide (OsO4)
* Ruthenium tetroxide (RuO4)
* Xenon tetroxide (XeO4)
* Iridium tetroxide (IrO4)
* Hassium tetroxide (HsO4)

Related|

* Oxocarbon
* Suboxide
* Oxyanion
* Ozonide
* Peroxide
* Superoxide

Oxides are sorted by oxidation state. Category:Oxides

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