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1916-07-0

Basic Information
CAS No.: 1916-07-0
Name: Methyl 3,4,5-trimethoxybenzoate
Article Data: 212
Molecular Structure:
Molecular Structure of 1916-07-0 (Methyl 3,4,5-trimethoxybenzoate)
Formula: C11H14O5
Molecular Weight: 226.229
Synonyms: 3,4,5-Trimethoxybenzoicacid methyl ester;Methyl eudesmate;Methylgallate trimethyl ether;Methyl tri-O-methylgallate;NSC 16955;Trimethylgallicacid methyl ester;
EINECS: 217-629-3
Density: 1.134 g/cm3
Melting Point: 81-85 °C
Boiling Point: 274.5 °C at 760 mmHg
Flash Point: 115.2 °C
Appearance: white to light yellow powder
Hazard Symbols: IrritantXi
Safety: 24/25
PSA: 53.99000
LogP: 1.49900
Synthetic route
67-56-1

methanol

118-41-2

Eudesmic acid

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid at 65℃; for 24h;100%
at 65℃; for 24h; Acidic conditions;100%
With sulfuric acid Reflux;97%
5470-42-8

N,N-diethyl(3,4,5-trimethoxyphenyl)carboxamide

420-37-1

trimethoxonium tetrafluoroborate

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: N,N-diethyl(3,4,5-trimethoxyphenyl)carboxamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation;
Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;
95%
99-24-1

methyl galloate

77-78-1

dimethyl sulfate

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 48h; Reflux;94.4%
With potassium carbonate In acetonitrile for 48h; Reflux;94.4%
With potassium carbonate In acetone for 0.25h; Etherification; methylation; microwave irradiation;81%
With potassium carbonate In acetone for 24h; Reflux;62.4%
118-41-2

Eudesmic acid

74-88-4

methyl iodide

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h;94%
With tetramethlyammonium chloride; sodium hydride 1.) hexane, 25 deg C, 30 min; 50 deg C, 2 h, 2.) methyl ethyl ketone, 50 - 60 deg C, 30 min, 3.) RT, 6 h;62%
With tetraethylammonium chloride; sodium hydride Product distribution; 1.) hexane, 25 deg C, 30 min; 50 deg C, 2 h, 2.) methyl ethyl ketone, 50 - 60 deg C, 30 min, 3.) RT, 6 h; other R4NCl, effect of the absence of quaternary ammonium salt;
67-56-1

methanol

86-81-7

3,4,5-trimethoxy-benzaldehyde

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With titanium silicate; dihydrogen peroxide for 12h; Heating;92%
With 3-mesityl-4-methylthiazol-3-ium bis((trifluoromethyl)sulfonyl)imide; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Electrochemical reaction; Inert atmosphere; Flow reactor;92%
With [bis(acetoxy)iodo]benzene; sodium bromide at 20℃; for 2h;88%
149-91-7

3,4,5-trihydroxybenzoic acid

aminomethyl phosphate

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: 3,4,5-trihydroxybenzoic acid; aminomethyl phosphate With sodium chloride; tin(ll) chloride; sodium sulfite at 45℃; for 1.33333h;
Stage #2: With potassium bisulfite for 4h; pH=10; pH-value; Temperature;
92%
149-91-7

3,4,5-trihydroxybenzoic acid

77-78-1

dimethyl sulfate

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Heating;89%
With potassium carbonate In acetone 1) 2h, roomtemp. 2) 48h, reflux;80%
With tetra-(n-butyl)ammonium iodide; potassium carbonate Reflux;78%
67-56-1

methanol

3840-31-1

(3,4,5-trimethoxyphenyl)methanol

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With bismuth(III) chloride; palladium diacetate; potassium carbonate at 20℃; for 2h; chemoselective reaction;89%
With Au#Co; oxygen; potassium carbonate at 80℃; under 750.075 Torr; for 12h; Autoclave;78%
With iodine; potassium carbonate for 19h; Heating;77%
67-56-1

methanol

(1H-pyrrol-1-yl)(3,4,5-trimethoxyphenyl)methanone

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 1h; Sealed tube; chemoselective reaction;89%
5658-49-1

N,N-dimethyl(3,4,5-trimethoxyphenyl)carboxamide

420-37-1

trimethoxonium tetrafluoroborate

1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: N,N-dimethyl(3,4,5-trimethoxyphenyl)carboxamide; trimethoxonium tetrafluoroborate With disodium hydrogenphosphate In acetonitrile at 20℃; Methylation;
Stage #2: With sodium hydrogencarbonate for 18h; Hydrolysis;
87%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is methyl 3,4,5-trimethoxybenzoate. With the CAS registry number 1916-07-0, it is also named as Trimethylgallic acid methyl ester. The product's categories are Aromatic Esters; C10 to C11; Carbonyl Compounds; Esters. It is white to light yellow powder which should be sealed in the container and stored in the cool and dry place. Additionally, people should avoid contact with skin and eyes. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 1.74; (5)ACD/BCF (pH 5.5): 12.29; (6)ACD/BCF (pH 7.4): 12.29; (7)ACD/KOC (pH 5.5): 209.68; (8)ACD/KOC (pH 7.4): 209.68; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.494; (13)Molar Refractivity: 58.06 cm3; (14)Molar Volume: 199.3 cm3; (15)Polarizability: 23.01×10-24 cm3; (16)Surface Tension: 34.2 dyne/cm; (17)Enthalpy of Vaporization: 51.29 kJ/mol; (18)Vapour Pressure: 0.00538 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 226.084124; (21)MonoIsotopic Mass: 226.084124; (22)Topological Polar Surface Area: 54; (23)Heavy Atom Count: 16; (24)Complexity: 216.

Preparation of Methyl 3,4,5-trimethoxybenzoate: It can be obtained by methylation reaction of gallic acid and dimethyl sulfate.

Uses of Methyl 3,4,5-trimethoxybenzoate: It can be used as pharmaceutical intermediate and is also the main raw material of anti-anxiety drugs trimetozine, intestinal medicine trimebutine maleate, etc. In addition, It can react with 4-methoxy-benzaldehyde to get (E)-3-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid. This reaction needs reagent Et3N and Ac2O by heating. The reaction time is 12 hours. The yield is 76%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1cc(OC)c(OC)c(OC)c1
2. InChI:InChI=1/C11H14O5/c1-13-8-5-7(11(12)16-4)6-9(14-2)10(8)15-3/h5-6H,1-4H3
  
The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07253,

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