554-95-0

Basic information

• Product Name: Trimesic acid
• Synonyms: 1,3,5-Tricarboxybenzene;5-Carboxyisophthalic acid;Trimesitinic acid;trimesitinicacid;Trimesinic acid;TRIMESIC ACID;1,3,5-BENZENETRICARBOXYLIC ACID;BENZENE-1,3,5-TRICARBOXYLIC ACID
• CAS NO: 554-95-0
• Molecular Formula: C₉H₆O₆
• Molecular Weight: 210.14
• EINECS: 209-077-7
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;Pyridines;addictives
• Mol File: 554-95-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 309.65°C (rough estimate)
• Flash Point: 328°C
• Appearance: white/Powder
• Density: 1.4844 (rough estimate)
• Vapor Pressure: 1.93E-13mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 26.3g/l
• PKA: pK1: 2.12;pK2: 4.10;pK3: 5.18 (25°C)
• Water Solubility: Soluble in water, ethanol and methanol.
• Stability: Stable, but may be light sensitive.
• BRN: 2053080
• CAS DataBase Reference: Trimesic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Trimesic acid(554-95-0)
• EPA Substance Registry System: Trimesic acid(554-95-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 554-95-0(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 554-95-0 differently. You can refer to the following data:
1. Trimesinic Acid is used for multifunctional therapeutics. It shows inhibitory activity against Torpedo Californica acetylcholinesterase and prevented amyloid-β peptide aggregate formation.
2. Trimesic acid is mainly used in the industry of poxy curing agent ,Adhesives and coating material ,Engineering plastic ,Synthetic fiber ,Cross-linking agent for alkyd resin ,Plasticizer ,Pharmaceutical intermediates, Desalination membrane etc.

Definition

ChEBI: Trimesic acid is a tricarboxylic acid that consists of benzene substituted by carboxy groups at positions 1, 3 and 5. It is a tricarboxylic acid and a member of benzoic acids. It is a conjugate acid of a benzene-1,3,5-tricarboxylate(1-).

General Description

This product has been enhanced for energy efficiency.

Flammability and Explosibility

Notclassified

Synthesis

Trimesic acid can be produced by Friedel – Crafts methylation of toluene or xylene with chloromethane in the presence of aluminum chloride.It is also formed by liquid-phase disproportionation of xylene in the presence of aluminum chloride.These reactions can be carried out in the gas phase at high temperature on aluminum silicate catalysts.

Purification Methods

Crystallise the acid from water. The trimethyl ester has m 144o (from MeOH or MeOH/H2O). [Beilstein 9 H 978, 9 IV 3747.]

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)/p-3

Synthetic route

1,3,5-trisbromobenzene (626-39-1) + carbon dioxide (124-38-9) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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%

3,5-dimethylbenzoic acid (499-06-9) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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

C23H16O7 → benzene-1,3,5-tricarboxylic acid (554-95-0)

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%

1,3,5-trimethyl-benzene (108-67-8) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (108-67-8) → 3,5-dimethylbenzoic acid (499-06-9) + benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (108-67-8) → isophthalic acid (121-91-5) + benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (108-70-3) + carbon monoxide (201230-82-2) → isophthalic acid (121-91-5) + benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (108-67-8) → 5-methylisophthalic aicd (499-49-0) + benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (499-06-9) → 5-methylisophthalic aicd (499-49-0) + benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With potassium dichromate; sulfuric acid

1,3,5-triacetylbenzene (779-90-8) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With sodium hypochlorite

5-methylisophthalic aicd (499-49-0) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With chromic acid
With potassium permanganate; calcined natrium carbonate; water

triethyl benzene-1,3,5-tricarboxylate (4105-92-4) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With potassium hydroxide

1,3,5-triethylbenzene (102-25-0) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With chromic acid

1,3,5-tris(hydroxymethyl)benzene (4464-18-0) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With nitric acid

benzenehexacarboxylic acid (517-60-2) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With glycerol

[1,1′:3′,1″-terphenyl]-5′-carboxylic acid (99710-75-5) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With chromium(III) oxide; sulfuric acid

5-sulfoisophthalic acid (22326-31-4) + potassium formate (590-29-4) → benzene-1,3,5-tricarboxylic acid (554-95-0)

3,5-dicarboxylic acid-1-benzoic acid methyl ester (18263-95-1) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With sodium hydroxide

benzene-1,3,5-tricarboxylic acid chloride (56961-24-1) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
With sodium amalgam

propargyl alcohol (107-19-7) → benzene-1,3,5-tricarboxylic acid (554-95-0) + 1,2,4-benzene tricarboxylic acid (528-44-9)

Conditions	Yield
With bis(triphenylphosphine)nickel(0) dicarbonyl; benzene Erwaermen des Reaktionsprodukts mit wss. Salpetersaeure;

ethylbenzene (100-41-4) + 1,2-dichloro-ethane (107-06-2) → benzene-1,3,5-tricarboxylic acid (554-95-0) + 1,2,4-benzene tricarboxylic acid (528-44-9)

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 (108-70-3) + carbon monoxide (201230-82-2) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (626-39-1) + carbon monoxide (201230-82-2) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (201230-82-2) + 3,5-dichlorobenzoic acid (51-36-5) → benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (108-67-8) → 3,5-dimethylbenzoic acid (499-06-9) + 5-methylisophthalic aicd (499-49-0) + benzene-1,3,5-tricarboxylic acid (554-95-0)

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 (859177-59-6) + bromine (7726-95-6) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
at 200℃;

nitric acid (7697-37-2) + 1,3,5-trimethyl-benzene (108-67-8) → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
at 200℃; under 29420.3 Torr;

Propiolic acid (471-25-0) + air → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
stehen an der Sonne;

hydrogen bromide (10035-10-6, 12258-64-9) + acetic acid (64-19-7) + 1,3,5-trimethyl-benzene (108-67-8) + air + cobalt naphthenate → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
at 205℃; under 20594.2 Torr;

magnesium acetate (142-72-3, 92123-19-8) + acetic acid (64-19-7) + 1,3,5-trimethyl-benzene (108-67-8) + air + magnesium bromide → benzene-1,3,5-tricarboxylic acid (554-95-0)

Conditions	Yield
at 196℃; under 20594.2 Torr; weitere Verbindungen: Ammoniumbromid, Kobaltnaphthenat;

methanol (67-56-1) + benzene-1,3,5-tricarboxylic acid (554-95-0) → 1,3,5-tris-(methoxycarbonyl)benzene (2672-58-4)

Conditions	Yield
With sulfuric acid	100%
With sulfuric acid at 72℃;	100%
With sulfuric acid for 24h; Heating;	99%

ethanol (64-17-5) + benzene-1,3,5-tricarboxylic acid (554-95-0) → triethyl benzene-1,3,5-tricarboxylate (4105-92-4)

Conditions	Yield
With hydrogenchloride Heating;	100%
With hydrogenchloride for 1h; Heating;	96.5%
With thionyl chloride at 0℃; for 12h; Reflux;	93%

benzene-1,3,5-tricarboxylic acid (554-95-0) → 1,3,5-benzene tris(carbonyl chloride) (4422-95-1)

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 (554-95-0) + N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-[(phenethylcarbamoyl-methyl)-amino]-acetamide; hydrochloride → benzene-1,3,5-tricarboxylic acid tris-[{[2-(3,4-dimethoxy-phenyl)-ethylcarbamoyl]-methyl}-(phenethylcarbamoyl-methyl)-amide]

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 (68076-36-8) + benzene-1,3,5-tricarboxylic acid (554-95-0) → 1,3,5-benzenetricarbonic acid tris-4-aminobutylamide (777055-97-7)

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 (554-95-0) + guanidine hydrogen carbonate (124-46-9, 20734-13-8, 100224-74-6, 593-85-1) + tetraethylammonium hydroxide (77-98-5) → C9H3O6(3-)*2C8H20N(1+)*CH5N3*H(1+)

Conditions	Yield
In water for 0.0833333h; Heating;	100%

benzene-1,3,5-tricarboxylic acid (554-95-0) + copper diacetate (142-71-2) → basolite C300

Conditions	Yield
for 0.166667h;	100%
In ethanol deposition on colloidal polystyrene crystal array;

benzene-1,3,5-tricarboxylic acid (554-95-0) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → 1,3,5-benzenetricarboxylic acid tetra(n-butyl)ammonium salt

Conditions	Yield
In methanol; water at 20℃;	100%
In methanol; water at 20℃;
In methanol at 20℃; for 2h;

copper nitrate hemi(pentahydrate) + benzene-1,3,5-tricarboxylic acid (554-95-0) → MOF-199

Conditions	Yield
In ethanol; water at 19.94 - 109.84℃; for 18.5h; Autoclave;	100%

benzene-1,3,5-tricarboxylic acid (554-95-0) + Ni(C8H16N6H4(CHCH3CH2C6H5)2)(2+)*2ClO4(1-)=Ni(C8H16N6H4(CHCH3CH2C6H5)2)(ClO4)2 + water (7732-18-5) + acetonitrile (75-05-8) → 3Ni(2+)*3C8H16N6H4(CHCH3CH2C6H5)2*2C6H3(CO2)3(3-)*12H2O*CH3CN=(NiC8H16N6H4(CHCH3CH2C6H5)2)3(C9H3O6)2*12H2O*CH3CN

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 (554-95-0) + N-[2-(tert-butoxycarbonylamino)ethyl]-2-(S)-amino-3-phenylpropionamide (383187-88-0) → C57H75N9O12

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%

bismuth (III) nitrate pentahydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) → [Bi(1,3,5-benzenetricarboxylate)(H2O)]·H2O

Conditions	Yield
In water at 130℃; for 0.0833333h; Sealed tube; Microwave irradiation;	99%

benzene-1,3,5-tricarboxylic acid (554-95-0) → 1,3,5-tris(hydroxymethyl)benzene (4464-18-0)

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 (71-23-8) + benzene-1,3,5-tricarboxylic acid (554-95-0) → tri-n-propyl benzene-1,3,5-tricarboxylate (56366-08-6)

Conditions	Yield
With hydrogenchloride for 1h; Heating;	97%

copper(II) nitrate hexahydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) → Cu2(OH)(benzene-1,3,5-tricarboxylate)(H2O)*2H2O

Conditions	Yield
In ethanol at 60℃; for 0.0833333h; Solvent; Temperature; Time; Flow reactor;	97%

benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) + cadmium(II) acetate dihydrate (5743-04-4) + N,N’-di(3-pyridyl)adipoamide (39642-63-2) → [Cd2(1,3,5-benzenetricarboxylic acid-(2H))2(N,N′-di(3-pyridyl)adipoamide)(H2O)2]·2H2O

Conditions	Yield
at 120℃; for 48h; Autoclave; High pressure;	97%

methanol (67-56-1) + benzene-1,3,5-tricarboxylic acid (554-95-0) → trimethyl 1,3,5-benzenetricarboxylate

Conditions	Yield
With sulfuric acid for 24h; Reflux;	97%

formic acid (64-18-6) + benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) + hafnium tetrachloride (13499-05-3) → Hf-MOF-808

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 48h;	97%

benzene-1,3,5-tricarboxylic acid (554-95-0) + 2-mercaptoethylamine hydrochloride (156-57-0) → N1,N3,N5-tris(2-mercaptoethyl)benzene-1,3,5-tricarboxamide

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%

copper(II) nitrate trihydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) → copper 1,3,5-benzenetricarboxylate

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 (7719-09-7) + benzene-1,3,5-tricarboxylic acid (554-95-0) → 1,3,5-benzene tris(carbonyl chloride) (4422-95-1)

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Reflux;	96%

copper(II) nitrate trihydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) → basolite C300

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 (617-84-5) + indium(III) nitrate hydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) + tetraethylammonium bromide (71-91-0) → (tetraethylammonium)3[In3(1,3,5-benzenetricarboxylate)4]*N,N-diethylformamide

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%

copper(II) nitrate trihydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) → Cu(2+)*C10H6O6(2-)*2.66H2O=Cu(C10H6O6)(H2O)*1.66H2O

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 (554-95-0) + [Ni(1,8-di((R)-α-methylnaphthyl)-1,3,6,8,10,13-hexaazacyclotetradecane)](ClO4)2 → [Ni(1,8-di((R)-α-methylnaphthyl)-1,3,6,8,10,13-hexaazacyclotetradecane)]3[C6H3(COO)3]2

Conditions	Yield
With triethylamine In acetonitrile	95%

benzene-1,3,5-tricarboxylic acid (554-95-0) + C74H127N9O23S2 → BTA[L-Phe-L-Met-L-Phe-L-Met-Ahx-D3-EG4]3

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 18h;	95%

benzene-1,3,5-tricarboxylic acid (554-95-0) + cyclohexylamine (108-91-8) → N1,N3,N5-tricyclohexylbenzene-1,3,5-tricarboxamide

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%

cerium(III) chloride heptahydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) + water (7732-18-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → {[Ce(BTC)(H2O)]•N,N-dimethylformamide}n

Conditions	Yield
at 115℃; for 36h; Temperature; High pressure;	94.4%

Upstream product

• 499-06-9 3,5-dimethylbenzoic acid 
• 779-90-8 1,3,5-triacetylbenzene 
• 499-49-0 5-methylisophthalic aicd 
• 4105-92-4 triethyl benzene-1,3,5-tricarboxylate 
• 102-25-0 1,3,5-triethylbenzene 
• 4464-18-0 1,3,5-tris(hydroxymethyl)benzene 
• 517-60-2 benzenehexacarboxylic acid 
• 99710-75-5 [1,1′:3′,1″-terphenyl]-5′-carboxylic acid 
• 22326-31-4 5-sulfoisophthalic acid 
• 590-29-4 potassium formate 
• 18263-95-1 3,5-dicarboxylic acid-1-benzoic acid methyl ester 
• 56961-24-1 benzene-1,3,5-tricarboxylic acid chloride 
• 107-19-7 propargyl alcohol 
• 108-67-8 1,3,5-trimethyl-benzene 

Downstream Products

• 204689-15-6 1,3,5-Tris(4,5-dihydro-1H-imidazol-2-yl)benzene 
• 2672-58-4 1,3,5-tris-(methoxycarbonyl)benzene 
• 4105-92-4 triethyl benzene-1,3,5-tricarboxylate 
• 71764-61-9 N,N'N-Trisphenyl-1,3,5-benzenetricarbonamide 
• 1684-47-5 1,3,5-trideuteriobenzene 
• 4422-95-1 1,3,5-benzene tris(carbonyl chloride) 
• 60541-32-4 benzene-1,3,5-tricarboxamide 
• 17832-16-5 triallyl benzene-1,3,5-tricarboxylate 
• 56366-08-6 tri-n-propyl benzene-1,3,5-tricarboxylate 
• 115695-23-3 DT-TM acid 
• 247048-22-2 1,3,5-benzene triscarboxylic acid tris(pentafluorophenyl) ester 
• 4464-18-0 1,3,5-tris(hydroxymethyl)benzene 
• 18226-42-1 1,3,5-Tris(bromomethyl)benzene 
• 352689-22-6 [(2-{3,5-bis-[2-(bis-ethoxycarbonylmethyl-amino)-ethylcarbamoyl]-benzoylamino}-ethyl)-ethoxycarbonylmethyl-amino]-acetic acid ethyl ester 

Relevant articles and documents

Photolabile dendrimers using o-nitrobenzyl ether linkages

(Formula presented) Benzyl aryl ether dendrimers containing photosensitive, veratryl-based o-nitrobenzyl AB linkages (bold bonds) were prepared to the third generation and shown to undergo site-specific degradation when irradiated with ultraviolet light.

Photo-induced deep aerobic oxidation of alkyl aromatics

Oxidation is a major chemical process to produce oxygenated chemicals in both nature and the chemical industry. Presently, the industrial manufacture of benzoic acids and benzene polycarboxylic acids (BPCAs) is mainly based on the deep oxidation of polyalkyl benzene, which is somewhat suffering from environmental and economical disadvantage due to the formation of ozone-depleting MeBr and corrosion hazards of production equipment. In this report, photo-induced deep aerobic oxidation of (poly)alkyl benzene to benzene (poly)carboxylic acids was developed. CeCl3 was proved to be an efficient HAT (hydrogen atom transfer) catalyst in the presence of alcohol as both hydrogen and electron shuttle. Dioxygen (O2) was found as a sole terminal oxidant. In most cases, pure products were easily isolated by simple filtration, implying large-scale implementation advantages. The reaction provides an ideal protocol to produce valuable fine chemicals from naturally abundant petroleum feedstocks. [Figure not available: see fulltext.].

Preparation method and application of trimellitic acid or trimesic acid

The invention belongs to the technical field of organic synthesis processes, and particularly relates to a preparation method and application of trimellitic acid or trimesic acid. According to the characteristics of the oxidation reaction process of 1,2,4-trimethylbenzene or mesitylene, two stages of reactors are connected in series, different oxidation reaction process conditions are respectively adopted, particularly, a second-stage reactor adopts a reaction strengthening technology, and an oxygen-enriched oxidation mode is adopted to strengthen the oxidation reaction process and increase the yield of the trimellitic acid or the trimesic acid.