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Cas Database |
| Name |
Trimesic acid |
EINECS | 209-077-7 |
| CAS No. | 554-95-0 | Density | 1.654 g/cm3 |
| PSA | 111.90000 | LogP | 0.78120 |
| Solubility | Soluble in water, ethanol and methanol. | Melting Point |
>300 °C(lit.) |
| Formula | C9H6O6 | Boiling Point | 561.422 °C at 760 mmHg |
| Molecular Weight | 210.143 | Flash Point | 307.391 °C |
| Transport Information | N/A | Appearance | off-white powder |
| Safety | 26-36/37/39-37/39 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| Synonyms |
1,3,5-Tricarboxybenzene;5-Carboxyisophthalic acid;NSC 3998;Trimesinic acid;Trimesitinic acid; |
Article Data | 101 |
Trimesic acid Synthetic route
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 |
- 554-95-0
benzene-1,3,5-tricarboxylic acid
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With potassium dichromate; sulfuric acid |
| Conditions | Yield |
|---|---|
| With sodium hypochlorite |
Trimesic acid 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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