573-11-5

Basic information

• Product Name: 2,3,4-Trimethoxybenzoic acid
• Synonyms: Benzoic acid, 2,3,4-trimethoxy-;AKOS 214-77;2,3,4-TRIMETHOXYBENZOIC ACID;LABOTEST-BB LT00454915;RARECHEM AL BO 0027;2,3,4-TRIMETHOXYBENZOIC ACID, 98+%;2,3,4-Trimethoxybenzoic;2,3,4-TRIMETHOXYBENZOIC ACID 99%
• CAS NO: 573-11-5
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.2
• EINECS: 209-350-0
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids;C10;Carbonyl Compounds;Carboxylic Acids
• Mol File: 573-11-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 99-102 °C(lit.)
• Boiling Point: 312.03°C (rough estimate)
• Flash Point: 123.5 °C
• Appearance: White to off-white/Crystalline Powder
• Density: 1.3006 (rough estimate)
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.5140 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.24±0.10(Predicted)
• BRN: 2696073
• CAS DataBase Reference: 2,3,4-Trimethoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-Trimethoxybenzoic acid(573-11-5)
• EPA Substance Registry System: 2,3,4-Trimethoxybenzoic acid(573-11-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 573-11-5(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO OFF-WHITE CRYSTALLINE POWDER

Uses

2,3,4-Trimethoxybenzoic acid was used in the synthesis of tropoloisoquinoline alkaloid pareitropone. It was also used in the synthesis of isomeric tris(pyrogallol) derivatives and naphthoic acid.

InChI:InChI=1/C10H12O5/c1-13-7-5-4-6(10(11)12)8(14-2)9(7)15-3/h4-5H,1-3H3,(H,11,12)/p-1

Synthetic route

2,3,4-trimethoxybenzaldehyde (2103-57-3) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With dihydrogen peroxide; potassium hydroxide In methanol; water for 8.5h; Reflux;	95%
With tert.-butylhydroperoxide; copper(l) chloride In acetonitrile at 20℃; for 2h;	91%
With permanganate(VII) ion
With potassium hydroxide; dihydrogen peroxide In methanol; water Heating;

C12H16O6 (1178514-38-9) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With niobium pentachloride In acetonitrile at 0 - 20℃; for 1h;	93%

malonic acid (141-82-2) + 1,2,3-trimethoxybenzene (634-36-6) → 2,3,4-Trimethoxy-benzoic acid (573-11-5) + 2,3,4-trimethoxybenzaldehyde (2103-57-3)

Conditions	Yield
With manganese triacetate In acetic acid for 0.0166667h; Heating; Yields of byproduct given;	A 9% B n/a

1,2,3-trimethoxybenzene (634-36-6) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With n-dodecyllithium; Petroleum ether anschliessend Behandeln mit festem Kohlendioxid unter Zusatz von Aether;
Multi-step reaction with 2 steps 1: hydrogen chloride; benzene; aluminium chloride / 0 - 40 °C / und nachfolgenden Zersetzen mit Eis 2: permanganate View Scheme
Multi-step reaction with 2 steps 1: aluminium chloride; carbon disulfide 2: alcoholic KOH-solution View Scheme
Multi-step reaction with 2 steps 1: AlCl3 / diethyl ether 2: aq. KOH / Heating View Scheme

2',3',4'-trimethoxyacetophenone (13909-73-4) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With sodium hypochlorite

methyl 2,3,4-trimethoxybenzoate (6395-18-2) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With potassium carbonate

2',3',4'-trimethoxychalcone (4082-16-0) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With permanganate(VII) ion; acetone

2,3,4-trimethoxybenzonitrile (43020-38-8) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With potassium hydroxide

(2,3,4-trimethoxy-phenyl)-glyoxylic acid methyl ester (105339-22-8) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With sodium hydroxide Behandeln der Reaktionsloesung mit wss. H2O2;

2,2,2-trichloro-1-(2,3,4-trimethoxy-phenyl)-ethanone → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With potassium hydroxide

methanol (67-56-1) + 2,3,4-trihydroxybenzoic acid (610-02-6) + dimethyl sulfate (77-78-1) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With potassium hydroxide

2-hydroxy-3,4-dimethoxybenzoic acid (5653-46-3) + dimethyl sulfate (77-78-1) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With sodium hydroxide die Loesung unter Zusatz von Aetznatron bezw. konz. Natronlauge kochen;
With sodium hydroxide

2,3,4-trimethoxybenzaldehyde (2103-57-3) → 2,3,4-trimethoxyphenol (19676-64-3) + 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With chloroform; ozone Erhitzen der Reaktionsprodukte mit Wasser, Zink und geringen Mengen Silbernitrat;

(2,3,4-trimethoxy-phenyl)-glyoxylonitrile (92288-79-4) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
With potassium hydroxide Heating;

chloroform (67-66-3) + ozone (10028-15-6) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → 2,3,4-trimethoxyphenol (19676-64-3) + 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
at 0℃; Erhitzen des Reaktionsprodukts mit Wasser,Zink-Pulver und wenig AgNO3;

2',3',4'-trimethoxychalcone (4082-16-0) + acetone (67-64-1) + potassium permanganate → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

sulfuric acid (7664-93-9) + (2,3,4-trimethoxy-phenyl)-glyoxylic acid (103988-63-2) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
Verduennen mit Wasser;

1,2,3-trimethoxybenzene (634-36-6) + n-dodecyllithium (1825-40-7) + petroleum ether → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
folgende Behandlung mit festem CO2;

methyl 2-hydroxy-3,4-dimethoxy-benzoate (6395-23-9) → 2,3,4-Trimethoxy-benzoic acid (573-11-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: diluted alkaline solution 2: NaOH-solution / die Loesung unter Zusatz von Aetznatron bezw. konz. Natronlauge kochen View Scheme

2,3,4-Trimethoxy-benzoic acid (573-11-5) + methyl iodide (74-88-4) → methyl 2,3,4-trimethoxybenzoate (6395-18-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 5h;	99%

1-indoline (496-15-1) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → indolin-1-yl(2,3,4-trimethoxyphenyl)methanone

Conditions	Yield
Stage #1: 2,3,4-Trimethoxy-benzoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 0 - 20℃; for 4h; Inert atmosphere; Stage #2: 1-indoline With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	99%

O-methylresorcine (150-19-6) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → 3-methoxyphenyl 2,3,4-trimethoxybenzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	98%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 2-hydroxy-3,4-dimethoxybenzoic acid (5653-46-3)

Conditions	Yield
With boron trichloride In n-heptane; dichloromethane at -78 - 20℃; for 3h; Inert atmosphere;	96.4%
With boron tribromide In dichloromethane at -20℃; for 0.5h;	62.2%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + 2-Amino-2-methyl-1-propanol (124-68-5) → 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)-4,5-oxazoline (85010-19-1)

Conditions	Yield
Stage #1: 2,3,4-Trimethoxy-benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 4h; Chlorination; Stage #2: 2-Amino-2-methyl-1-propanol With thionyl chloride In dichloromethane at 20℃; for 12h; Cyclization;	96%

para-bromotoluene (106-38-7) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → C16H18O5S

Conditions	Yield
With palladium diacetate; caesium carbonate; sodium sulfate In N,N-dimethyl-formamide at 150℃; for 12h; Inert atmosphere;	95%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 3,4,5-(trimethoxy)benzoyl chloride (7169-07-5)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In toluene for 3.5h;	94%
With thionyl chloride; sodium hydroxide In water; benzene for 2h; Reflux;	85%
With phosphorus pentachloride

3,4-dimethoxyphenol (2033-89-8) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → 3,4-dimethoxyphenyl 2,3,4-trimethoxybenzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	93%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + propionic acid anhydride (123-62-6) → 2,3,4-trimethoxy-6-propionylbenzoic acid

Conditions	Yield
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3,5-trimethyl-benzene at 145℃; for 16h; Inert atmosphere; Glovebox;	92%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 5-(chlorosulfonyl)-2,3,4-trimethoxybenzoic acid (926251-22-1)

Conditions	Yield
With chlorosulfonic acid at 20℃; for 4h;	91%
With chlorosulfonic acid In dichloromethane at 75℃; for 8h; Cooling with ice;

2,3,4-Trimethoxy-benzoic acid (573-11-5) + o-hydroxyacetophenone (118-93-4) → C18H18O6 (1563185-99-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h; Inert atmosphere;	89%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + C15H29N3O5 → 4-(2,3-bis(tert-butoxycarbonyl)guanidino)butyl 2,3,4-trimethoxybenzoate

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	89%

1-bromo-butane (109-65-9) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → butyl 2,3,4-trimethoxybenzoate (139214-91-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;	87%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153165-85-6) → <1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-2,3,4-tris-(methoxy)-benzamide (153165-93-6)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran for 4h; Ambient temperature;	86%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 2,3,4-trimethoxybenzoic anhydride (111798-15-3)

Conditions	Yield
With methanesulfonyl chloride; triethylamine In tetrahydrofuran at 0℃; for 1h;	85%
With pyridine; thionyl chloride; diethyl ether

2,3,4-Trimethoxy-benzoic acid (573-11-5) + Tosyl isocyanate (4083-64-1) → N-Ts-2,3,4-trimethoxybenzamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 60℃;	85%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 2,3-dihydroxy-4-methoxybenzoic acid (3934-81-4)

Conditions	Yield
With boron trichloride In dichloromethane at 0 - 20℃; for 11h; Inert atmosphere;	83%
With boron trichloride In dichloromethane at 0 - 20℃; for 14.17h;	76%
With boron trichloride In dichloromethane Ambient temperature;	74%
Stage #1: 2,3,4-Trimethoxy-benzoic acid With hydrogen iodide; acetic acid at 20 - 80℃; for 10h; Stage #2: With sodium hydroxide In water at 20℃; for 1h; pH=1.5;	73%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + 1S-(1α,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153221-51-3) → <1R-(1α,4α,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-2,3,4-tris-(methoxy)-benzamide (153221-61-5)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran for 4h; Ambient temperature;	82%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + 4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butan-1-amine (392660-78-5) → 2,3,4-trimethoxy-N-(4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butyl)benzamide (1353004-52-0)

Conditions	Yield
Stage #1: 2,3,4-Trimethoxy-benzoic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: 4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butan-1-amine In tetrahydrofuran at 20℃;	82%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 1,5-diiodo-2,3,4-trimethoxybenzene (174518-80-0)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; lithium iodide In 1,1,1,3,3,3-hexafluoroisopropanol at 20℃; Hunsdiecker type reaction;	81%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + phenyl isocyanate (103-71-9) → 4,5,6-trimethoxy-2-phenylisoindoline-1,3-dione (101569-30-6)

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate In 1,4-dioxane at 100℃; for 36h; Inert atmosphere;	81%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylic acid (2292-40-2)

Conditions	Yield
With manganese(IV) oxide; di-μ-chlorobis(norbornadiene)dirhodium(I) In water at 150℃; for 24h; Sealed tube; regiospecific reaction;	81%
With rhodium(III) chloride trihydrate; tetrabutylammonium acetate In N,N-dimethyl-formamide at 80℃; for 20h; Electrolysis;

Nicotinic acid hydrazide (553-53-7) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → 3-[5-(2,3,4-trimethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-pyridine

Conditions	Yield
With trichlorophosphate for 0.25h; microwave irradiation;	79%

2-methoxybenzoylhydrazine (7466-54-8) + 2,3,4-Trimethoxy-benzoic acid (573-11-5) → 2-(2-methoxy-phenyl)-5-(2,3,4-trimethoxy-phenyl)-[1,3,4]oxadiazole

Conditions	Yield
With trichlorophosphate for 0.25h; microwave irradiation;	76%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + diethylamine (109-89-7) → 2-(diethylamino)-3,4-dimethoxybenzoic acid (1224865-54-6)

Conditions	Yield
Stage #1: diethylamine With n-butyllithium In hexane at -30 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,3,4-Trimethoxy-benzoic acid In tetrahydrofuran; hexane at -30 - 0℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 0℃; pH=7; Inert atmosphere;	76%
Stage #1: diethylamine With n-butyllithium In tetrahydrofuran; hexane at -30 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,3,4-Trimethoxy-benzoic acid In tetrahydrofuran; hexane at -30 - 0℃; for 4h; Stage #3: With hydrogenchloride In water pH=7;	76%

2,3,4-Trimethoxy-benzoic acid (573-11-5) → 2,3,4-trimethoxy-6-nitrobenzoic acid (61948-84-3)

Conditions	Yield
With nitric acid at 0℃; for 0.166667h;	75%
With nitric acid at 0℃; for 0.166667h;	69%
With nitric acid In water at 0℃; for 1.16667h;	69%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + methyl iodide (74-88-4) + 2,3-dimethylbenzoic acid (603-79-2) → C21H24O7

Conditions	Yield
Stage #1: 2,3,4-Trimethoxy-benzoic acid; 2,3-dimethylbenzoic acid With manganese(IV) oxide; di-μ-chlorobis(norbornadiene)dirhodium(I) In water at 150℃; for 24h; Sealed tube; Stage #2: methyl iodide With potassium carbonate In water; acetone at 60℃; for 24h; regiospecific reaction;	75%

2,3,4-Trimethoxy-benzoic acid (573-11-5) + 1R-(1β,4α,5β,6β) 4-amino-5,6-bis<(4-methoxyphenyl)methoxy>-2-cyclohexen-1-ol (153165-86-7) → <1R-(1α,4β,5β,6β)> N-<5,6-bis-<(4-methoxyphenyl)methoxy>-4-hydroxy-2-cyclohexen-1-yl>-2,3,4-tris-(methoxy)-benzamide

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In tetrahydrofuran for 4h; Ambient temperature;	72%

Upstream product

• 43020-38-8 2,3,4-trimethoxybenzonitrile 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 141-82-2 malonic acid 
• 634-36-6 1,2,3-trimethoxybenzene 
• 4082-16-0 2',3',4'-trimethoxychalcone 
• 67-64-1 acetone 
• 1178514-38-9 C₁₂H₁₆O₆ 
• 6395-23-9 methyl 2-hydroxy-3,4-dimethoxy-benzoate 
• 1825-40-7 n-dodecyllithium 
• 7664-93-9 sulfuric acid 
• 103988-63-2 (2,3,4-trimethoxy-phenyl)-glyoxylic acid 
• 67-66-3 chloroform 
• 10028-15-6 ozone 
• 92288-79-4 (2,3,4-trimethoxy-phenyl)-glyoxylonitrile 

Downstream Products

• 4304-23-8 2,3,4-trimethoxy-benzoic acid amide 
• 61948-84-3 2,3,4-trimethoxy-6-nitrobenzoic acid 
• 18646-77-0 4,5,6-trimethoxy-isophthalic acid 
• 860518-52-1 1,2,3-trimethoxy-4,5-dinitro-benzene 
• 71989-96-3 2,3,4-trimethoxybenzylalcohol 
• 109394-76-5 2,3,4-trimethoxy-benzoic acid-(2-dimethylamino-ethyl ester) 
• 111798-15-3 2,3,4-trimethoxybenzoic anhydride 
• 7169-07-5 3,4,5-(trimethoxy)benzoyl chloride 
• 64059-58-1 (trimethoxy-2,3,4 phenyl) (morpholino-4)methanone 
• 125928-15-6 (2-Thioxo-thiazolidin-3-yl)-(2,3,4-trimethoxy-phenyl)-methanone 
• 139214-91-8 butyl 2,3,4-trimethoxybenzoate 
• 87359-15-7 2-(2,3,4-Trimethoxyphenyl)-1H-imidazo<4,5-c>pyridine dihydrochloride 
• 85010-19-1 4,4-dimethyl-2-(2,3,4-trimethoxyphenyl)-4,5-oxazoline 
• 953387-95-6 3,4-dimethoxyphenyl 2,3,4-trimethoxybenzoate 

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