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 |
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℃; |
1,3,5-trimethyl-benzene
A
3,5-dimethylbenzoic acid
B
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% |
1,3,5-trimethyl-benzene
A
isophthalic acid
B
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; water; dihydrogen peroxide; manganese(II) bromide at 380℃; under 172517 Torr; | A n/a B 78% |
1,3,5-trichlorobenzene
carbon monoxide
A
isophthalic acid
B
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% |
1,3,5-trimethyl-benzene
A
5-methylisophthalic aicd
B
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. |
3,5-dimethylbenzoic acid
A
5-methylisophthalic aicd
B
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With potassium dichromate; sulfuric acid |
Conditions | Yield |
---|---|
With sodium hypochlorite |
Conditions | Yield |
---|---|
With chromic acid | |
With potassium permanganate; calcined natrium carbonate; water |
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With chromic acid |
Conditions | Yield |
---|---|
With nitric acid |
Conditions | Yield |
---|---|
With glycerol |
[1,1′:3′,1″-terphenyl]-5′-carboxylic acid
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With chromium(III) oxide; sulfuric acid |
5-sulfoisophthalic acid
potassium formate
benzene-1,3,5-tricarboxylic acid
3,5-dicarboxylic acid-1-benzoic acid methyl ester
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
benzene-1,3,5-tricarboxylic acid chloride
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium amalgam |
propargyl alcohol
A
benzene-1,3,5-tricarboxylic acid
B
1,2,4-benzene tricarboxylic acid
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(0) dicarbonyl; benzene Erwaermen des Reaktionsprodukts mit wss. Salpetersaeure; |
ethylbenzene
1,2-dichloro-ethane
A
benzene-1,3,5-tricarboxylic acid
B
1,2,4-benzene tricarboxylic acid
Conditions | Yield |
---|---|
With aluminium trichloride Erhitzen des Reaktionsprodukts mit HNO3 auf 180grad; | |
With aluminium trichloride Erwaermen des Reaktionsprodukts mit HNO3 auf 180grad; |
1,3,5-trichlorobenzene
carbon monoxide
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dicobalt octacarbonyl In ethanol; water at 65℃; under 1471.02 Torr; for 20h; Product distribution; Irradiation; | 85.5 % Chromat. |
1,3,5-trisbromobenzene
carbon monoxide
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dicobalt octacarbonyl In ethanol; water at 65℃; under 1471.02 Torr; for 4h; Product distribution; Irradiation; | 93.4 % Chromat. |
carbon monoxide
3,5-dichlorobenzoic acid
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dicobalt octacarbonyl In water at 65℃; under 1471.02 Torr; for 20h; Product distribution; Irradiation; | 88.6 % Chromat. |
1,3,5-trimethyl-benzene
A
3,5-dimethylbenzoic acid
B
5-methylisophthalic aicd
C
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With oxygen; dibromo-bis-triphenylphosphine cobalt In acetic acid at 140℃; under 7500.6 Torr; for 5.16667h; Product distribution; other cobalt bromide complexes; other time; other solvents; |
1,3,6-trioxo-hexahydro-4,7-etheno-furo[3,4-c]pyran-9-carboxylic acid methyl ester
bromine
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
at 200℃; |
Conditions | Yield |
---|---|
at 200℃; under 29420.3 Torr; |
Conditions | Yield |
---|---|
stehen an der Sonne; |
hydrogen bromide
acetic acid
1,3,5-trimethyl-benzene
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
at 205℃; under 20594.2 Torr; |
magnesium acetate
acetic acid
1,3,5-trimethyl-benzene
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
at 196℃; under 20594.2 Torr; weitere Verbindungen: Ammoniumbromid, Kobaltnaphthenat; |
methanol
benzene-1,3,5-tricarboxylic acid
1,3,5-tris-(methoxycarbonyl)benzene
Conditions | Yield |
---|---|
With sulfuric acid | 100% |
With sulfuric acid at 72℃; | 100% |
With sulfuric acid for 24h; Heating; | 99% |
ethanol
benzene-1,3,5-tricarboxylic acid
triethyl benzene-1,3,5-tricarboxylate
Conditions | Yield |
---|---|
With hydrogenchloride Heating; | 100% |
With hydrogenchloride for 1h; Heating; | 96.5% |
With thionyl chloride at 0℃; for 12h; Reflux; | 93% |
Conditions | Yield |
---|---|
With thionyl chloride In N,N-dimethyl-formamide for 8h; Heating; | 100% |
With thionyl chloride In N,N-dimethyl-formamide for 3h; Heating; | 100% |
With thionyl chloride; N,N-dimethyl-formamide for 3h; Heating / reflux; | 100% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In chloroform; N,N-dimethyl-formamide at 25℃; for 16h; Substitution; | 100% |
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
benzene-1,3,5-tricarboxylic acid
1,3,5-benzenetricarbonic acid tris-4-aminobutylamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 8h; | 100% |
benzene-1,3,5-tricarboxylic acid
guanidine hydrogen carbonate
tetraethylammonium hydroxide
Conditions | Yield |
---|---|
In water for 0.0833333h; Heating; | 100% |
Conditions | Yield |
---|---|
for 0.166667h; | 100% |
In ethanol deposition on colloidal polystyrene crystal array; |
Conditions | Yield |
---|---|
In methanol; water at 20℃; | 100% |
In methanol; water at 20℃; | |
In methanol at 20℃; for 2h; |
Conditions | Yield |
---|---|
In ethanol; water at 19.94 - 109.84℃; for 18.5h; Autoclave; | 100% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile a soln. of benzenetricarboxylic acid and N(C2H5)3 in a mixt. CH3CN0H2O (3:1 v/v) was added dropwise to a soln. of Ni-complex in CH3CN; filtered, washed with CH3CN, H2O, diethyl ether, dried in air; elem. anal.; | 99% |
benzene-1,3,5-tricarboxylic acid
N-[2-(tert-butoxycarbonylamino)ethyl]-2-(S)-amino-3-phenylpropionamide
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1.5h; Inert atmosphere; | 99% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
In water at 130℃; for 0.0833333h; Sealed tube; Microwave irradiation; | 99% |
Conditions | Yield |
---|---|
Stage #1: benzene-1,3,5-tricarboxylic acid With methanol; sulfuric acid Inert atmosphere; Schlenk technique; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran Inert atmosphere; Schlenk technique; | 98% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; | 91% |
With lithium aluminium tetrahydride In tetrahydrofuran |
propan-1-ol
benzene-1,3,5-tricarboxylic acid
tri-n-propyl benzene-1,3,5-tricarboxylate
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Heating; | 97% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
In ethanol at 60℃; for 0.0833333h; Solvent; Temperature; Time; Flow reactor; | 97% |
benzene-1,3,5-tricarboxylic acid
water
cadmium(II) acetate dihydrate
N,N’-di(3-pyridyl)adipoamide
Conditions | Yield |
---|---|
at 120℃; for 48h; Autoclave; High pressure; | 97% |
Conditions | Yield |
---|---|
With sulfuric acid for 24h; Reflux; | 97% |
formic acid
benzene-1,3,5-tricarboxylic acid
water
hafnium tetrachloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 48h; | 97% |
Conditions | Yield |
---|---|
Stage #1: benzene-1,3,5-tricarboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 40℃; for 1h; Stage #2: 2-mercaptoethylamine hydrochloride With triethylamine at 49 - 50℃; for 1h; | 96.4% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
In ethanol; water; N,N-dimethyl-formamide at 80℃; for 24h; Sealed tube; | 96% |
With lauric acid In butan-1-ol at 20℃; for 2h; | |
With sodium acetate In ethanol; water at 20℃; for 0.5h; Reagent/catalyst; Concentration; |
thionyl chloride
benzene-1,3,5-tricarboxylic acid
1,3,5-benzene tris(carbonyl chloride)
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 8h; Reflux; | 96% |
Conditions | Yield |
---|---|
In water at 70℃; for 12.33h; Sealed tube; | 95% |
In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 12.5h; Concentration; Temperature; Sonication; | 92% |
With triethyl amine In ethanol; water; N,N-dimethyl-formamide High Pressure; benzenecarboxylic acid dissolved in DMF/EtOH/H2O (1:1:1 v/v), Cu(NO3)2 dissolved in the same DMF/EtOH/H2O mixt., solns. combined, stirred, Et3N added, stirred for 24 h under reflux (ca. 120°C); filtered, washed (DMF/EtOH/H2O 1:1:1), dried (60°C, 5 h); XRD, contains Cu2O (by XRD); | 73.1% |
N-formyldiethylamine
benzene-1,3,5-tricarboxylic acid
tetraethylammonium bromide
Conditions | Yield |
---|---|
In further solvent(s) C6H3(COOH)3, (C2H5)4NBr, In(NO3)3*xH2O in N,N-diethylformamide was heated at 120°C for 4 days, cooled to room temp.; washed with ethanol; elem. anal.; | 95% |
Conditions | Yield |
---|---|
In methanol; water High Pressure; Cu nitrate and acid dissolved in MeOH/H2O in stainless steel autoclave; stirred for 15 min at ambient temp.; heated in oven at 383 K for 7 d; naturally cooled down to room temp.; filtered, washed with water and acetone, dried in air; | 95% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With triethylamine In acetonitrile | 95% |
benzene-1,3,5-tricarboxylic acid
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 18h; | 95% |
Conditions | Yield |
---|---|
Stage #1: benzene-1,3,5-tricarboxylic acid With bis(trichloromethyl) carbonate; N,N-dimethyl-formamide In ethyl acetate at 25 - 65℃; for 8h; Stage #2: cyclohexylamine In ethyl acetate at 78℃; for 7.5h; | 94.8% |
tricresole borate In xylene for 8h; Product distribution / selectivity; Heating / reflux; | 79.2% |
benzene-1,3,5-tricarboxylic acid
water
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 115℃; for 36h; Temperature; High pressure; | 94.4% |
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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