Trimellitic anhydride

An aromatic carboxylic acid, C9H4O5, 192.126 g/mol. Boiling point 390 °C, melting point 161-163.5 °C, as published.

verified recordOrganic — aromatic carboxylic acid6 measured properties

Identifiers

Molecular formula: C₉H₄O₅
Molecular weight: 192.126 g/mol
Exact mass: 192.005873 g/mol
IUPAC name: 1,3-dioxo-2-benzofuran-5-carboxylic acid
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

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 464 to 473 °F at 14 mmHg (NTP, 1992)measured · CAMEO Chemicals; 390 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point: 329 to 336 °F (NTP, 1992)measured · CAMEO Chemicals; 161-163.5 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Density: 1.55 at 68 °F (NTP, 1992) - Denser than water; will sinkmeasured · CAMEO Chemicals; 1.55 at 68 °Fmeasured · Occupational Safety and Health Administration (OSHA)
Solubility: less than 1 mg/mL at 68 °F (NTP, 1992)measured · CAMEO Chemicals; 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 · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 4e-06 mmHg at 77 °F (NTP, 1992)measured · CAMEO Chemicals; 0.00000986 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Flash Point: 440.6 °F (NTP, 1992)measured · CAMEO Chemicals; 227 °C o.c.measured · ILO-WHO International Chemical Safety Cards (ICSCs)

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 192.12 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 192.00587322 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 0.8calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 80.7 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 308calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 1calculated · reference compound database
H-bond acceptors: 5calculated · reference compound database
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

The systematic name on this record is 1,3-dioxo-2-benzofuran-5-carboxylic acid.

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.

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

reference compound database11089
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.