569-51-7

Basic information

• Product Name: 1,2,3-Benzenetricarboxylic acid
• Synonyms: 1,2,3-Benzenetricarboxylic acid (anhydrous);1,2,3-Tricarboxybenzene;1,2,3-BENZENETRICARBOXYLIC ACID;1,2,3-BENZENTRICARBOXYLIC ACID;1,2,3-TRIBENZOIC ACID;HEMIMELLITIC ACID;BENZENE-1,2,3-TRICARBOXYLIC ACID;Hemimelliticacid,96%
• CAS NO: 569-51-7
• Molecular Formula: C₉H₆O₆
• Molecular Weight: 210.14
• EINECS: 209-317-0
• Product Categories: Organic acids
• Mol File: 569-51-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: ~195 °C (dec.)
• Boiling Point: 309.65°C (rough estimate)
• Flash Point: 265.1 °C
• Appearance: white to almost white crystalline powder
• Density: 1.5460
• Vapor Pressure: 1.81E-10mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pK1: 2.88;pK2: 4.75;pK3: 7.13 (25°C)
• Water Solubility: 30.6g/L(19 oC)
• BRN: 2214816
• CAS DataBase Reference: 1,2,3-Benzenetricarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-Benzenetricarboxylic acid(569-51-7)
• EPA Substance Registry System: 1,2,3-Benzenetricarboxylic acid(569-51-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 569-51-7(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystalline powder

InChI:InChI=1/C9H6O6/c10-7(11)4-2-1-3-5(8(12)13)6(4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)

Synthetic route

1,2,3-trimethylbenzene (526-73-8) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With air; acetic acid; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; cobalt(II) acetate; zirconyl acetate at 150℃; under 15200 Torr; for 6h;	81%
With sodium hydroxide; potassium permanganate In water for 2h; Heating;	80%
Stage #1: 1,2,3-trimethylbenzene With potassium permanganate; potassium hydroxide In water at 95℃; for 4.08333h; Reflux; Stage #2: With sulfuric acid In water at 45℃; for 2h; Reagent/catalyst;	80.67%
With nitric acid

3-(ethoxymethyl)phthalic acid disodium salt → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate In water at 20℃; for 18h;	42%

1,8-Naphthalic anhydride (81-84-5) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
Reaktion ueber mehrere Stufen;
Multi-step reaction with 2 steps 1: NaOH; water / man gibt eine konzentrierte Loesung von KMnO4 in Wasser hinzu 2: water; KMnO4 View Scheme

1,6-dimethylnaphthalene (575-43-9) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium hydroxide; potassium permanganate

fluoranthene (206-44-0) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium hydroxide; potassium permanganate

3-methylphthalic acid (37102-74-2) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate

acide 2,6-carboxyphenylglyoxalique (3112-43-4) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate; water

2-acetyl-6-methyl-benzoic acid (56661-76-8) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate; sodium carbonate Ansaeuern des Reaktionsgemisches mit Schwefelsaeure;

dimethyl 3-cyanobenzene-1,2-dicarboxylate (103856-64-0) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With sodium hydroxide

5,10,15-trioxo-10,15-dihydro-5H-diindeno[1,2-a;1',2'-c]fluorene-1,6,11-tricarboxylic acid → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate

acenaphthene (83-32-9) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium hydroxide; potassium permanganate

acenaphthene quinone (82-86-0) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With alkaline permanganate

2,3-dimethylbenzoic acid (603-79-2) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With nitric acid
With potassium permanganate at 100℃;

Hemimellitsaeure-dimethyl-(1,2)-aethyl-(3)-ester (17603-10-0) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium hydroxide In ethanol

9-hydroxy-1-oxophenalene (7465-58-9) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With sodium hydroxide; potassium permanganate In water Heating;

2,3-dihydro-4-methyl-1H-indene (824-22-6) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate In sodium hydroxide Heating; overnight;

3-methyl-9-hydroxyphenalen-1-one (77204-12-7) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With sodium hydroxide; potassium permanganate In water Heating;

C17H16O2 (33979-11-2) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With potassium permanganate; sodium carbonate In water

2,4-dibromo-naphthalene-1,8-dicarboxylic acid (22516-52-5) → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
With sodium hydroxide; potassium permanganate

1,3-dioxo-1,3-dihydro-isoindole-4-carboxylic acid (776-22-7) + alkali carbonate → benzene-1,2,3-tricarboxlic acid (569-51-7)

1,3-dioxo-1,3-dihydro-isoindole-4-carboxylic acid (776-22-7) + alkaline solution → benzene-1,2,3-tricarboxlic acid (569-51-7)

isoquinoline-5-carboxylic acid (27810-64-6) + potassium permanganate → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
at 100℃; in neutraler Loesung;

6-hydroxy-7-oxo-cyclohepta-1,3,5-triene-1,2-dicarboxylic acid-anhydride (14371-38-1) + sodium hydroxide → benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
at 180℃;

acenaphthene (83-32-9) + alkaline aqueous KMnO4 → carbon dioxide (124-38-9) + benzene-1,2,3-tricarboxlic acid (569-51-7) + acide 2,6-carboxyphenylglyoxalique (3112-43-4) + oxalic acid (144-62-7)

1,1-dimethyl-3-oxo-phthalan-4,5-dicarboxylic acid (108171-24-0) + potassium hydroxide → benzene-1,2,3-tricarboxlic acid (569-51-7) + acetone (67-64-1)

acenaphthene quinone (82-86-0) + alkaline permanganate → Naphthalene-1,8-dicarboxylic acid (518-05-8) + benzene-1,2,3-tricarboxlic acid (569-51-7) + acide 2,6-carboxyphenylglyoxalique (3112-43-4)

2,3-dimethylbenzoic acid (603-79-2) + alkaline permanganate → benzene-1,2,3-tricarboxlic acid (569-51-7)

1,1,4-trimethylcycloheptane (2158-55-6) + selenium → terephthalic acid (100-21-0) + benzene-1,2,3-tricarboxlic acid (569-51-7)

Conditions	Yield
at 390 - 400℃; anschliessende Oxydation mit KMnO4 in wss.-alkal. Loesung;

1,6-dimethylnaphthalene (575-43-9) + alkaline aqueous KMnO4-solution → carbon dioxide (124-38-9) + benzene-1,2,3-tricarboxlic acid (569-51-7) + oxalic acid (144-62-7) + acetic acid (64-19-7)

benzene-1,2,3-tricarboxlic acid (569-51-7) → 3-carboxyphthalic anhydride (3786-39-8)

Conditions	Yield
In tetrahydrofuran at 150℃; for 6h;	99%
at 190 - 200℃;
at 150℃; for 12h;

4,4'-bipyridine (553-26-4) + copper(II) nitrate trihydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) + water (7732-18-5) + sodium hydroxide (1310-73-2) → copper(I,II)(2-hydroxyisophthalate)(4,4'-bipyridine) + [semi(4,4'-bipyridine)bis(2-oxyisophthalate)tricopper(II)] dihydrate

Conditions	Yield
In water High Pressure; Cu:acid:4,4'-bipy:NaOH=1:1:0.5:4, heated in autoclave at 170°C for 3 d; crysts. separated manually, washed (water, ethanol); elem. anal.;	A 95% B 2%

benzene-1,2,3-tricarboxlic acid (569-51-7) → 1,3,5-tris-(methoxycarbonyl)benzene (2672-58-4)

Conditions	Yield
With sulfuric acid In methanol for 24h; Reflux;	94%

benzene-1,2,3-tricarboxlic acid (569-51-7) → Tri-K-Salz von Hemimellitsaeure (15999-91-4, 63507-68-6, 66760-38-1)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol	88%

benzene-1,2,3-tricarboxlic acid (569-51-7) + water (7732-18-5) + cadmium(II) acetate dihydrate (5743-04-4) + N,N’-di(3-pyridyl)adipoamide (39642-63-2) → [Cd(1,2,3-benzenetricarboxylic acid-(2H))(N,N′-di(3-pyridyl)adipoamide)(H2O)]·H2O

Conditions	Yield
at 120℃; for 48h; Autoclave; High pressure;	86%

cobalt(II) nitrate hexahydrate + 1,3-di(4-pyridyl)propane (17252-51-6) + benzene-1,2,3-tricarboxlic acid (569-51-7) + water (7732-18-5) → [tetracobalt(II)(μ3-OH)2(1,2,3-benzenetricarboxylate)2(1,3-bis(4-pyridyl)propane)2(H2O)2]*1,3-bis(4-pyridyl)propane

Conditions	Yield
With Et3N In water High Pressure; mixt. of Co salt, C6H3(COOH)3, Et3N, (C5H4N)2C3H6 and H2O treated in autoclave at 175°C for 60 h; cooled to room temp. at a rate of 5°C/h; elem. anal., detd. by TGA;	85%

zinc(II) nitrate hexahydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) + 1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5) + water (7732-18-5) → {[Zn2(1,4-bis((1H-imidazol-1-yl)methyl)benzene)(BTC)(OH)]*H2O}n

Conditions	Yield
With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure;	66%

4,4'-bipyridine (553-26-4) + copper(II) nitrate trihydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) → [sesqui(4,4'-bipyridine)bis(isophthalate)copper(I,II)]

Conditions	Yield
With NaOH In water High Pressure; Cu:acid:4,4'-bipy:NaOH=1:1:0.5:2, heated in autoclave at 170°C for 3 d; crysts. washed (water, ethanol); elem. anal.;	65%

copper(II) nitrate trihydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) → catena-[aqua(μ5-benzene-1,2,3-tricarboxylato-κO:κO':κO'':κO''':κO'''':κO''''')(μ-hydroxo)dicopper(II)]

Conditions	Yield
In water High Pressure; mixt. Cu(NO3)2*3H2O, benzene-1,2,3-tricarboxylic acid and water was stirred at room temp. for 30 min and heated in Teflon-lined stainless-steel autoclave at 170°C for 50 h; react. mixt. was cooled to room temp. at 10°C/h, ppt. was filtered, washed with water and dried in air; elem. anal.;	65%

thallium(I) nitrate + benzene-1,2,3-tricarboxlic acid (569-51-7) → [Tl3(μ-1,2,3-benzenetricarboxylic acid-3H)]n

Conditions	Yield
With KOH In methanol; water soln. of (C6H3)(COOH)3 (1 mmol) in MeOH stirred with aq. KOH (3 mmol); aq. soln. of TlNO3 (3 mmol) added; refluxed (1 h); filtered; evapd. (several d); washed with acetone; dried in air; elem. anal.;	65%

cobalt(II) acetate dihydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) + zinc(II) acetate dihydrate (5970-45-6) + N,N′-bis(3-pyridyl)succinamide (39642-62-1) → [Zn2.40Co0.60(N,N′-bis(3-pyridyl)succinamide)(1,2,3-benzenetricarboxylate)2(H2O)6]*4H2O

Conditions	Yield
With sodium hydroxide at 120℃; for 48h; High pressure;	65%

1,10-Phenanthroline (66-71-7) + benzene-1,2,3-tricarboxlic acid (569-51-7) + zinc(II) acetate dihydrate (5970-45-6) → C33H20N4O6Zn

Conditions	Yield
In water at 120℃; for 72h; Temperature; Autoclave;	65%

manganese(II) chloride tetrahydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) + 1-(4-(1H-imidazole-5-yl)phenyl)-1H-1,2,4-triazole + water (7732-18-5) → C11H10N5(1+)*C9H3O6(3-)*H2O*Mn(2+)

Conditions	Yield
With sodium hydroxide at 140℃; for 72h; pH=7; Sealed tube;	62%

1,4-pyrazine (290-37-9) + benzene-1,2,3-tricarboxlic acid (569-51-7) + silver nitrate → [[Ag(1,2,3-benzenetricarboxylic acid(-1H))(pyrazine)](H2O)2](n)

Conditions	Yield
With KOH In water High Pressure; pyrazine was added to aq. soln. of AgNO3 and 1,2,3-benzenetricarboxylic acid; pH was adjusted to 7.0 with dropwise addition of dilute KOH; placed in Teflon-lined stainless steel vessel; heated at 120°C for 3 ds; slowly cooled to room temp.; crystals were obtained; elem. anal.;	61%

benzene-1,2,3-tricarboxlic acid (569-51-7) + water (7732-18-5) + cadmium(II) hydroxide → [tetraaqua-bis(dihydrogen benzene-1,2,3-tricarboxylato-κO'')cadmium(II) dihydrate]

Conditions	Yield
In water High Pressure; mixt. Cd(OH)2, benzene-1,2,3-tricarboxylic acid and water was stirred atroom temp. for 30 min and heated in Teflon-lined stainless-steel autocl ave at 170°C for 3 d; react. mixt. was cooled to room temp. at 8°C/h, ppt. was filtered, washed with water and dried in air; elem. anal.;	60%

benzene-1,2,3-tricarboxlic acid (569-51-7) + water (7732-18-5) + silver nitrate → [Ag(μ2-H2O)(μ2-1,2,3-benzenetricarboxylic acid(-H))]*1.5H2O

Conditions	Yield
With Nd(NO3)3*6H2O In water aq. soln. of Ag compd.(0.25 mmol), ligand (0.33 mmol), and Nd compd. (0.125 mmol) refluxed for 2 h; cooled, filtered, crystd. on storage for 2 wk, elem. anal.;	60%

benzene-1,2,3-tricarboxlic acid (569-51-7) + zinc(II) acetate dihydrate (5970-45-6) + N,N′-bis(3-pyridyl)succinamide (39642-62-1) → [Zn(1,2,3-benzenetricarboxylate)(H2O)](H2-N,N'-di(3-pyridyl)succinamide)0.5*2H2O

Conditions	Yield
With sodium hydroxide In water at 120℃; for 48h; Autoclave;	60%

zinc(II) nitrate hexahydrate + benzene-1,2,3-tricarboxlic acid (569-51-7) + 1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5) → [(zinc(II))2(hydroxy)(μ4-benzene-1,2,3-tricaboxylate)(1,4-bis(imidazol-1-ylmethyl)benzene)] dihydrate

Conditions	Yield
With LiOH*H2O In water High Pressure; soln. of Zn(NO3)2*6H2O (0.1 mmol), H3BTC (0.1 mmol), bix (0.1 mmol) and LiOH*H2O (0.3 mmol) heated in Teflon-lined stainless steel autoclave at 140°C for 3 d; filtered, washed (H2O and EtOH); elem. anal.;	58%

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 575-43-9 1,6-dimethylnaphthalene 
• 526-73-8 1,2,3-trimethylbenzene 
• 206-44-0 fluoranthene 
• 37102-74-2 3-methylphthalic acid 
• 3112-43-4 acide 2,6-carboxyphenylglyoxalique 
• 56661-76-8 2-acetyl-6-methyl-benzoic acid 
• 103856-64-0 dimethyl 3-cyanobenzene-1,2-dicarboxylate 
• 83-32-9 acenaphthene 
• 82-86-0 acenaphthene quinone 
• 603-79-2 2,3-dimethylbenzoic acid 
• 17603-10-0 Hemimellitsaeure-dimethyl-(1,2)-aethyl-⁽³⁾-ester 
• 7465-58-9 9-hydroxy-1-oxophenalene 
• 824-22-6 2,3-dihydro-4-methyl-1H-indene 

Downstream Products

• 2672-57-3 benzene-1,2,3-tricarboxylic acid trimethyl ester 
• 91345-28-7 benzene-1,2,3-tricarboxylic acid-1,3-dimethyl ester 
• 3807-81-6 5-nitro-1,2,3-benzenetricarboxylic acid 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 24821-23-6 2,6-Di-(trifluormethyl)-benzamid 
• 313-13-3 2,6-bis-trifluoromethyl-aniline 
• 24821-20-3 2,6-Bis-trifluormethyl-acetanilid 

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