Trimellitic anhydride

C9H4O5, 192.126 g/mol. Its structure, the values that were measured, the values that were calculated, and where each one came from.

Organic — aromatic carboxylic acid6 measured properties

Drawn from the SMILES. It shows how the atoms are connected — not a photograph of a molecule, and not its shape in space.

Identifiers

Molecular formula: C₉H₄O₅
Molecular weight: 192.126 g/mol
Exact mass: 192.005873 g/mol
SMILES: O=C(O)c1ccc2c(c1)C(=O)OC2=O
InChI: InChI=1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
InChIKey: SRPWOOOHEPICQU-UHFFFAOYSA-N

Open in ReactionLens Use in reaction prediction

Both are open without an account.

Measured properties

Values somebody obtained from a sample and published. Where two sources report the same property they are both shown, in the units each used — a disagreement between them is information, and averaging it away would be inventing a number neither one gave.

Boiling Point: 464 to 473 °F at 14 mmHg (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 390 °Cmeasured · Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V18: 1026 (1996); Boiling point: 240-245 °C at 14 mm Hgmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1729; Boiling point 240-245 °C at 14 mm Hgmeasured · Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V18: 1026 (1996); at 1.87kPa: 240-245 °Cmeasured · reference compound database; 464-473 °F at 14 mmHgmeasured · reference compound database
Melting Point: 329 to 336 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 161-163.5 °Cmeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1729; 161-163.5 °Cmeasured · reference compound database; 329-336 °Fmeasured · reference compound database; 322 °Fmeasured · reference compound database
Flash Point: 440.6 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 227 °C o.c.measured · reference compound database; 440.6 °Fmeasured · reference compound database
Solubility: less than 1 mg/mL at 68 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; Sol at 25 °C: 0.002 g/100 g carbon tetrachloride; 0.06 g/100 g ligroin; 0.4 g/100 g mixed xylenes; 15.5 g/100 g dimethyl formamide; 49.6 g/100 g acetone; 21.6 g/100 g ethyl acetatemeasured · O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1729; 36.5 g/100 g 2-butanone at 25 °C; 38.4 g/100 g cyclohexanone at 25 °C; 0.06 g/100 g mineral spirits at 25 °Cmeasured · Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V18: 1026 (1996); Solubility in water: reactionmeasured · reference compound database
Density: 1.55 at 68 °F (NTP, 1992) - Denser than water; will sinkmeasured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 1.55 at 68 °Fmeasured · reference compound database
Vapor Pressure: 4e-06 mmHg at 77 °F (NTP, 1992)measured · National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.; 0.00000986 [mmHg]measured · reference compound database; Vapor pressure: 4X10-6 mm Hgmeasured · American Conference of Governmental Industrial Hygienists, Inc. Documentation of the Threshold Limit Values, 4th ed., 1980. Cincinnati, Ohio: American Conference of Governmmental Industrial Hygienists, Inc., 1980., p. 415; Vapor pressure of liquid trimellitic anhydride = 2.25 mm Hg at 200 °Cmeasured · Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V18: 1026 (1996); Vapor pressure at 25 °C: negligiblemeasured · reference compound database; 0.000004 mmHgmeasured · reference compound database; 0.000004 mmHgmeasured · reference compound database

Calculated properties

Derived from the structure rather than from a sample. These are reproducible and they are not measurements: a calculated partition coefficient and a measured one can differ by a long way, and where both exist they are listed apart on purpose.

logP: 0.6954calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 80.67 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 1calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 4calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 1calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 43.1473 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.5227calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

C Carbon9 atoms · 56.3% by mass
O Oxygen5 atoms · 41.6% by mass
H Hydrogen4 atoms · 2.1% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 14
Total atoms, hydrogen included: 18
Rings: 2
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Carboxylic acid
A carbon double-bonded to oxygen and bonded to an –OH group; acidic.
Ester
A carbonyl bonded to an oxygen that links to another carbon.
Ether
An oxygen bridging two carbons.
Aromatic ring
A flat six-membered ring with delocalised electrons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Trimellitic anhydride yet.

Other names for it

No systematic name is recorded.

The sources also call it 1,2,4-Benzenetricarboxylic anhydride, Anhydrotrimellitic acid, Trimellitic acid anhydride, 4-Carboxyphthalic anhydride, TMAN, Trimellitic acid 1,2-anhydride, Trimellic acid anhydride, 1,3-Dihydro-1,3-dioxo-5-isobenzofurancarboxylic acid, 1,3-Dioxo-5-phthalancarboxylic acid, Trimellic acid 1,2-anhydride, 1,3-Dioxo-1,3-dihydro-2-benzofuran-5-carboxylic acid, Trimellitic acid cyclic 1,2-anhydride.

Structurally related

Nothing structurally close to Trimellitic anhydride has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Trimellitic anhydride. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

1,3-dioxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

formed as a product

C₁₈H₂₂N₂O₄, 330.384 g/mol.

Where these values came from

chemistry engine
structure perception

No matching record was found in the currently indexed sources (reference compound database)..

What this page does not claim

The identifiers are what the source record holds, copied rather than recomputed. Measured values are reported as their source gave them, units and all; calculated values are marked as calculated and are not measurements. Where a field is absent the page says so, because a blank cell reads as a zero and a guessed value reads as a fact.

Nothing here is a hazard assessment, a purity statement or advice about handling a sample. A flash point quoted from a safety database is a number somebody published, not a judgement by us about whether this molecule is safe for what you intend.