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554-95-0

Basic Information
CAS No.: 554-95-0
Name: Trimesic acid
Article Data: 101
Molecular Structure:
Molecular Structure of 554-95-0 (Trimesic acid)
Formula: C9H6O6
Molecular Weight: 210.143
Synonyms: 1,3,5-Tricarboxybenzene;5-Carboxyisophthalic acid;NSC 3998;Trimesinic acid;Trimesitinic acid;
EINECS: 209-077-7
Density: 1.654 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 561.422 °C at 760 mmHg
Flash Point: 307.391 °C
Solubility: Soluble in water, ethanol and methanol.
Appearance: off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39-37/39
PSA: 111.90000
LogP: 0.78120
Synthetic route
626-39-1

1,3,5-trisbromobenzene

124-38-9

carbon dioxide

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.333333h; Schlenk technique;
Stage #2: 1,3,5-trisbromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 20h; Schlenk technique; Sealed tube;
97%
Stage #1: carbon dioxide With o-phenylenebis(diphenylphosphine); copper(II) acetate monohydrate In 1,4-dioxane at 65℃; for 0.416667h; Schlenk technique;
Stage #2: 1,3,5-trisbromobenzene With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; toluene at 100℃; for 16h; Schlenk technique;
97%
499-06-9

3,5-dimethylbenzoic acid

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With zirconium(II) acetate; triethanolamine; oxygen; cobalt(II) acetate; manganese(II) acetate; acetic acid; potassium bromide at 80℃; for 7h; Reagent/catalyst; Temperature; Reflux;95%
With chromic acid
With nitric acid
Multi-step reaction with 2 steps
1: K2cr2O7; diluted sulfuric acid
2: chromic acid mixture
View Scheme

C23H16O7

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With 2-H-1,3-di-tert-butyl-1,3,2-diazaphosphorinane; 2,2'-azobis(isobutyronitrile); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 90℃; for 12h; chemoselective reaction;92%
108-67-8

1,3,5-trimethyl-benzene

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With potassium permanganate; cetyltrimethylammonim bromide In water at 85℃; for 1h;90%
With potassium permanganate; water at 95℃;
With potassium permanganate; water at 95℃;
108-67-8

1,3,5-trimethyl-benzene

A

499-06-9

3,5-dimethylbenzoic acid

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
Stage #1: 1,3,5-trimethyl-benzene With C96H72Cr2N8O; C36H24CuN8; 2-hydroxy-6-nitro-1H-isoindole-1,3-dione at 120℃; under 3750.38 Torr; for 3h;
Stage #2: With acetic acid at 180℃; under 7500.75 Torr; for 2.5h;
Stage #3: With acetic acid at 235℃; under 18001.8 Torr; for 1.8h; Reagent/catalyst; Temperature; Pressure; Overall yield = 96.8 %;
A 14.4%
B 82.4%
108-67-8

1,3,5-trimethyl-benzene

A

121-91-5

isophthalic acid

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; water; dihydrogen peroxide; manganese(II) bromide at 380℃; under 172517 Torr;A n/a
B 78%
108-70-3

1,3,5-trichlorobenzene

201230-82-2

carbon monoxide

A

121-91-5

isophthalic acid

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; cobalt(II) acetate In ethanol at 65℃; under 1520 Torr; for 18h; Irradiation;A 21.3%
B 76.4%
108-67-8

1,3,5-trimethyl-benzene

A

499-49-0

5-methylisophthalic aicd

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With air; acetic acid; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; zirconyl acetate at 120℃; under 15200 Torr; for 6h; Product distribution; Further Variations:; Catalysts; Temperatures;A 25%
B 65%
With oxygen; triethanolamine; sodium bromide; cobalt(II) bromide In acetic acid at 140℃; under 8250.7 Torr; for 2h; Product distribution; other time, other catalyzator;A 5.7 % Chromat.
B 82.8 % Chromat.
499-06-9

3,5-dimethylbenzoic acid

A

499-49-0

5-methylisophthalic aicd

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid
779-90-8

1,3,5-triacetylbenzene

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
With sodium hypochlorite
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Specification

The Trimesic acid , with cas registry number of 554-95-0, is also called Trimesinic acid ; 1,3,5-Benzenetricarboxylic acid with the IUPAC name of benzene-1,3,5-tricarboxylic acid . Its systematic name is also called benzene-1,3,5-tricarboxylic acid . Trimesic acid is a benzene derivative with three carboxylic acid groups. It also belongs to the product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic acids. This compound is stable, but may be sensitive to light.

Physical properties of Trimesic acid : (1) H bond acceptors: 6 ; (2) H bond donors: 3 ; (3) Freely Rotating Bonds: 3 ; (4) Index of Refraction: 1.662 ; (5) Molar Refractivity: 47.04 cm3 ; (6) Molar Volume: 127 cm3 ; (7) Surface Tension: 92.2 dyne/cm ; (8) Enthalpy of Vaporization: 88.83 kJ/mol ; (9) Vapour Pressure: 1.93E-13 mmHg at 25°C.

Preparation of Trimesic acid : a lot of chemicals can prepare this compound. For example, 1,3,5-trimethyl-benzene can be used to prepare Trimesic acid using the reagents of Potassium permanganate , and cetyltrimethylammonium bromide in the solvent of water under temperature of 85 ℃ for 1 hours. The yield is about 90%.

Uses of Trimesic acid : (1) uses in organic synthesis: Trimesic acid can be used to prepare many chemicals such as 1,3,5-tris-trifluoromethyl-benzene . The reaction occures under the temperature of 170 ℃ in the presence of reagents of SF4 for 48 hours. The yield is about 90%. (2) uses in the industry: Trimesic acid is mainly used as poxy curing agent, Adhesives and coating material, Engineering plastic, Synthetic fiber, Cross-linking agent for alkyd resin, Plasticizer, Pharmaceutical intermediates, Desalination membrane, etc.

When you are using this chemical, please be cautious about it as the following:
The Trimesic acid irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)c1cc(cc(C(=O)O)c1)C(=O)O;
(2)InChI:InChI=1/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15);
(3)InChIKey:QMKYBPDZANOJGF-UHFFFAOYAC

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