610-02-6

Basic information

• Product Name: 2,3,4-Trihydroxybenzoic acid
• Synonyms: 2,3,4-trihydroxy-benzoicaci;4-pyrogallolcarboxylicacid;RARECHEM AL BE 0036;PYROGALLIC ACID-4-CARBOXYLIC ACID;PYROGALLOL-4-CARBOXYLIC ACID;PYROGALLOL CARBOXYLIC ACID;AKOS AUF2096;1,2,3-BENZENETRIOL-4-CARBOXYLIC ACID
• CAS NO: 610-02-6
• Molecular Formula: C₇H₆O₅
• Molecular Weight: 170.12
• EINECS: 210-205-9
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 610-02-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: ~205 °C (dec.)(lit.)
• Boiling Point: 259.73°C (rough estimate)
• Flash Point: 232.543 °C
• Appearance: White to off-white/Powder
• Density: 1.4663 (rough estimate)
• Vapor Pressure: 1.99E-08mmHg at 25°C
• Refractive Index: 1.6400 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.30±0.13(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 2210807
• CAS DataBase Reference: 2,3,4-Trihydroxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Trihydroxybenzoic acid(610-02-6)
• EPA Substance Registry System: 2,3,4-Trihydroxybenzoic acid(610-02-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DH8900000
• Hazardous Substances Data: 610-02-6(Hazardous Substances Data)

Usage

Chemical Properties

White to brown powder

Uses

2,3,4-Trihydroxybenzoic Acid is used in preparation of Polyester Polyol for solar backboard coating adhesive.

General Description

DPPH radical-scavenging ability of 2,3,4-trihydroxybenzoic acid has been evaluated.

Purification Methods

Crystallise the acid from water. [Beilstein 10 IV 1971.]

InChI:InChI=1/C7H6O5/c8-4-2-1-3(7(11)12)5(9)6(4)10/h1-2,8-10H,(H,11,12)/p-1

Synthetic route

C6H7O5 → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With hydrogenchloride for 2.5h;	96%

9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one (298-81-7) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
bei der Kalischmelze;

3-formyl-2, 4-dihydroxybenzoic acid (4435-88-5) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

diphenylamine (122-39-4) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With water; sodium hydrogencarbonate; sodium sulfate
With potassium hydrogencarbonate at 160 - 170℃; im Leuchtgas-Strom;

2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzoic acid (610-02-6) + 4,5,6-trihydroxyisophthalic acid (27163-60-6)

Conditions	Yield
With ammonium carbonate; water at 130℃;

potassium hydrogencarbonate (298-14-6) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

1,2,3-trimethoxybenzene (634-36-6) + potassium hydrogencarbonate (298-14-6) → 2,3,4-trihydroxybenzoic acid (610-02-6)

4-hydroxysalicylic acid (89-86-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With water (γ-irradiation);
With ferrous(II) sulfate heptahydrate; dihydrogen peroxide In water at 20℃; pH=2.5; Fenton reaction; UV-irradiation;

2-hydroxyresorcinol (87-66-1) + KHCO3 → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
at 115℃;
With diphenylamine
at 115℃;

2-hydroxyresorcinol (87-66-1) + potassium dicarbonate → 2,3,4-trihydroxybenzoic acid (610-02-6)

water (7732-18-5) + 2-hydroxyresorcinol (87-66-1) + potassium dicarbonate → 3,4,5-trihydroxybenzoic acid (149-91-7) + 2,3,4-trihydroxybenzoic acid (610-02-6)

water (7732-18-5) + 2-hydroxyresorcinol (87-66-1) + ammonium carbonate → 2,3,4-trihydroxybenzoic acid (610-02-6) + 4,5,6-trihydroxyisophthalic acid (27163-60-6)

Conditions	Yield
at 130℃;

benzoic acid (65-85-0) → 2,3-Dihydroxybenzoic acid (303-38-8) + 2,5-dihydroxybenzoic acid. (490-79-9) + 2,3,4-trihydroxybenzoic acid (610-02-6) + 3-Carboxyphenol (99-06-9) + salicylic acid (69-72-7) + 4-hydroxy-benzoic acid (99-96-7) + 2,4-, 2,6-, 3,4-, 3,5-dihydroxybenzoic acids, 2,3,5- 2,4,5- 3,4,5-trihydroxybenzoic acids, phenol, ...

Conditions	Yield
With hydrogenchloride; oxygen; iron(III) chloride In water Product distribution; Rate constant; Mechanism; hydroxylation by electrochemical Fenton reaction at pH=1, reaction time dependence;

2-hydroxyresorcinol (87-66-1) + ammonium carbonate → 2,3,4-trihydroxybenzoic acid (610-02-6) + pyrogalloldicarboxylic acid

Conditions	Yield
at 130℃;

ω-chloro-2.3.4-triacetoxy-acetophenone → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With potassium permanganate; acetone Behandlung des Reaktionsprodukts mit alkoh. Salzsaeure;

carbon dioxide (124-38-9) + 2-hydroxyresorcinol (87-66-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With potassium hydrogencarbonate at 135℃;

2-hydroxyresorcinol (87-66-1) + aqueous potassium dicarbonate → 2,3,4-trihydroxybenzoic acid (610-02-6)

carbon dioxide (124-38-9) + aqueous pyrogallol → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
With sodium amalgam

2-hydroxyresorcinol (87-66-1) + ammonium carbonate → 2,3,4-trihydroxybenzoic acid (610-02-6) + 4,5,6-trihydroxyisophthalic acid (27163-60-6)

Conditions	Yield
With water at 130℃;

2,3,4-trihydroxy-dithiobenzoic acid (32361-59-4) + concentrated KOH-solution → 2,3,4-trihydroxybenzoic acid (610-02-6)

2-chloro-1-(2,3,4-triacetoxy-phenyl)-ethanone + acetone (67-64-1) + KMnO4 → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
anschliessend Einw. des Reaktionsprodukts mit alkoh. Salzsaeure;

acetyl fraxinol (28752-90-1) → 2,3,4-trihydroxybenzoic acid (610-02-6)

Conditions	Yield
Stage #1: acetyl fraxinol With potassium permanganate Stage #2: With hydrogen iodide In acetic acid for 4h; Heating;

methanol (67-56-1) + 2,3,4-trihydroxybenzoic acid (610-02-6) → 2,3,4-trihydroxybenzoic acid methyl ester (56128-66-6)

Conditions	Yield
With molecular sieve; sulfuric acid for 120h; Heating;	98%
With toluene-4-sulfonic acid for 0.333333h; Microwave, 510 W;	90%
With hydrogenchloride
With sulfuric acid Heating;
With hydrogenchloride

3,5-dihydroxyphenol (108-73-6) + 2,3,4-trihydroxybenzoic acid (610-02-6) → 1,3,5,6-tetrahydroxy-xanthen-9-one (5084-31-1)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 100℃; for 0.25h;	98%
With zinc(II) chloride; trichlorophosphate at 65℃; for 4.5h; Inert atmosphere;	62%
With zinc(II) chloride; trichlorophosphate at 65℃; for 3h; Inert atmosphere;	52%

2,3,4-trihydroxybenzoic acid (610-02-6) + chloromethyl methyl ether (107-30-2) → 2,3,4-tris-methoxymethoxy-benzoic acid methoxymethyl ester (280136-86-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; Condensation;	98%

2,3,4-trihydroxybenzoic acid (610-02-6) → 2,3,4-trihydroxybenzoic acid methyl ester (56128-66-6)

Conditions	Yield
With sulfuric acid In methanol	98%
With thionyl chloride

2,3,4-trihydroxybenzoic acid (610-02-6) + methyl iodide (74-88-4) → 2,3,4-trihydroxybenzoic acid methyl ester (56128-66-6)

Conditions	Yield
Stage #1: 2,3,4-trihydroxybenzoic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 12h;	95%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 12h;	95%
Stage #1: 2,3,4-trihydroxybenzoic acid With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 40℃;	92%
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 40℃;

2,3,4-trihydroxybenzoic acid (610-02-6) + p-methoxybenzyl chloride (824-94-2) → 4-methoxybenzyl 2,3,4-tris((4-methoxybenzyl)oxy)benzoate (1338708-48-7)

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 70℃;	93%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; Inert atmosphere;	92%

2,3,4-trihydroxybenzoic acid (610-02-6) + 2-hydroxyresorcinol (87-66-1) → 2,3,4,3',4',5'-hexahydroxybenzophenone (52479-85-3)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Friedel-Crafts reaction;	90%
Stage #1: 2,3,4-trihydroxybenzoic acid; 2-hydroxyresorcinol With zinc(II) chloride; trichlorophosphate at 70℃; for 2.5h; Stage #2: With water at 4℃; for 24h; Cooling with ice;	90%

2,3,4-trihydroxybenzoic acid (610-02-6) + potassium hydrogencarbonate (298-14-6) → 4,5,6-trihydroxyisophthalic acid (27163-60-6)

Conditions	Yield
In water at 180℃; High pressure;	82%

2,3,4-trihydroxybenzoic acid (610-02-6) + benzyl bromide (100-39-0) → benzyl 2,3,4-tris(benzyloxy)benzoate (1609113-44-1)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone Reflux;	81%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 120℃;
With potassium carbonate In acetone for 8h; Reflux;

2,3,4-trihydroxybenzoic acid (610-02-6) + isoprene (78-79-5) → 3,4-dihydro-7,8-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid (86635-77-0)

Conditions	Yield
With phosphoric acid In xylene at 35℃; for 8h;	80%

2,3,4-trihydroxybenzoic acid (610-02-6) → 4-nitro-1,2,3-trimethoxybenzene (76088-63-6)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 50 - 60℃; for 0.25h;	70%

2,3,4-trihydroxybenzoic acid (610-02-6) + C18H21NO3 → methyl 4-(2-isopropyl-5-methylphenoxy)-3-(2,3,4-trihydroxybenzamido)benzoate

Conditions	Yield
With phosphorus trichloride In toluene at 110℃; for 0.5h; Microwave irradiation;	68%

2,3,4-trihydroxybenzoic acid (610-02-6) + 2-(4-(bromomethyl)phenyl)-N-isobutylbenzo[d]oxazole-7-carboxamide → 4-(7-(isobutylcarbamoyl)benzo[d]oxazol-2-yl)benzyl-2,3,4-trihydroxy-benzoate

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 45℃;	54.1%

diethyl sulfate (64-67-5) + 2,3,4-trihydroxybenzoic acid (610-02-6) → 2,3,4-triethoxybenzoic acid

Conditions	Yield
With sodium hydroxide In water for 6h; Reflux;	53.5%

2,3,4-trihydroxybenzoic acid (610-02-6) + dimethyl sulfate (77-78-1) → 2-hydroxy-3,4-dimethoxybenzoic acid (5653-46-3)

Conditions	Yield
With sodium hydroxide In methanol	42%
With sodium hydroxide

2,3,4-trihydroxybenzoic acid (610-02-6) + methyl iodide (74-88-4) → methyl 2-hydroxy-3,4-dimethoxy-benzoate (6395-23-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 68h;	40%

2,3,4-trihydroxybenzoic acid (610-02-6) + ethyl acetoacetate (141-97-9) → 7,8-dihydroxy-4-methyl-2-oxo-2H-chromene-6-carboxylic acid (855286-70-3)

Conditions	Yield
With sulfuric acid at 20℃; for 6h; Pechmann condensation;	40%

2,3,4-trihydroxybenzoic acid (610-02-6) + 3-chloro-aniline (108-42-9) → N-(3-chloro-phenyl)-2,3,4-trihydroxy-benzamide

Conditions	Yield
With phosphorus trichloride In dibutyl ether at 140℃; for 4h;	37%

orcinol (504-15-4) + 2,3,4-trihydroxybenzoic acid (610-02-6) → 1,5,6-trihydroxy-3-methyl-9H-xanthen-9-one (106738-75-4)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 90℃;	33%
With zinc(II) chloride; trichlorophosphate

2,3,4-trihydroxybenzoic acid (610-02-6) + acetone (67-64-1) → 7,8-dihydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (1204201-77-3)

Conditions	Yield
With trifluoroacetic anhydride In trifluoroacetic acid at 0℃; for 19h;	31%

diazomethane (186581-53-3, 908094-01-9) + 2,3,4-trihydroxybenzoic acid (610-02-6) → methyl 2,3,4-trimethoxybenzoate (6395-18-2)

Conditions	Yield
With diethyl ether

ethanol (64-17-5) + 2,3,4-trihydroxybenzoic acid (610-02-6) → ethyl 2,3,4-trihydroxybenzoate (90536-71-3)

Conditions	Yield
With hydrogenchloride at 60 - 70℃; in einer Druckflasche;
With hydrogenchloride
With sulfuric acid Heating;

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide (20757-83-9) + 2,3,4-trihydroxybenzoic acid (610-02-6) → 4-hydroxybenzo[d][1,3]dioxole-5-carboxylic acid (4776-00-5)

Conditions	Yield
With sodium hydroxide; acetone unter Ausschluss von Luft;

2,3,4-trihydroxybenzoic acid (610-02-6) → 2,3,4-trihydroxy-benzoyl chloride

Conditions	Yield
With thionyl chloride

2,3,4-trihydroxybenzoic acid (610-02-6) → 5-bromo-2,3,4-trihydroxy-benzoic acid (861605-86-9)

Conditions	Yield
With bromine; acetic acid

2,3,4-trihydroxybenzoic acid (610-02-6) + acetic anhydride (108-24-7) → triacetylgallic acid (855291-88-2)

Upstream product

• 87-66-1 2-hydroxyresorcinol 
• 298-14-6 potassium hydrogencarbonate 
• 7732-18-5 water 
• 65-85-0 benzoic acid 
• 124-38-9 carbon dioxide 
• 28752-90-1 acetyl fraxinol 
• 67-64-1 acetone 
• 32361-59-4 2,3,4-trihydroxy-dithiobenzoic acid 
• 89-86-1 4-hydroxysalicylic acid 
• 634-36-6 1,2,3-trimethoxybenzene 
• 122-39-4 diphenylamine 
• 4435-88-5 3-formyl-2, 4-dihydroxybenzoic acid 
• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 

Downstream Products

• 90536-71-3 ethyl 2,3,4-trihydroxybenzoate 
• 75440-84-5 exifone 
• 74919-03-2 2,3,4-Trihydroxy-benzoic acid 2-oxo-2-phenyl-ethyl ester 
• 86635-77-0 3,4-dihydro-7,8-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylic acid 
• 27163-60-6 4,5,6-trihydroxyisophthalic acid 
• 87-66-1 2-hydroxyresorcinol 
• 1346859-93-5 tetradecyl 2,3,4-trihydroxybenzoate 
• 17345-73-2 4,6-dibromo-pyrogallol 
• 74919-10-1 6,7,8-Trihydroxy-4-phenyl-isochromen-1-one 
• 5653-45-2 2,5-dihydroxy-3,4-dimethoxy-benzoic acid 
• 280136-86-9 2,3,4-tris-methoxymethoxy-benzoic acid methoxymethyl ester 
• 861605-86-9 5-bromo-2,3,4-trihydroxy-benzoic acid 
• 6395-23-9 methyl 2-hydroxy-3,4-dimethoxy-benzoate 

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