Product Name

  • Name

    Methyl 3,4,5-trimethoxybenzoate

  • EINECS 217-629-3
  • CAS No. 1916-07-0
  • Article Data212
  • CAS DataBase
  • Density 1.134 g/cm3
  • Solubility
  • Melting Point 81-85 °C
  • Formula C11H14O5
  • Boiling Point 274.5 °C at 760 mmHg
  • Molecular Weight 226.229
  • Flash Point 115.2 °C
  • Transport Information
  • Appearance white to light yellow powder
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 1916-07-0 (Methyl 3,4,5-trimethoxybenzoate)
  • Hazard Symbols IrritantXi
  • Synonyms 3,4,5-Trimethoxybenzoicacid methyl ester;Methyl eudesmate;Methylgallate trimethyl ether;Methyl tri-O-methylgallate;NSC 16955;Trimethylgallicacid methyl ester;
  • PSA 53.99000
  • LogP 1.49900

Synthetic route

methanol
67-56-1

methanol

Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzoic acid methyl ester
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%
N,N-diethyl(3,4,5-trimethoxyphenyl)carboxamide
5470-42-8

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

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

3,4,5-trimethoxybenzoic acid methyl ester
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%
methyl galloate
99-24-1

methyl galloate

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4,5-trimethoxybenzoic acid methyl ester
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%
Eudesmic acid
118-41-2

Eudesmic acid

methyl iodide
74-88-4

methyl iodide

3,4,5-trimethoxybenzoic acid methyl ester
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;
methanol
67-56-1

methanol

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

3,4,5-trimethoxybenzoic acid methyl ester
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%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

aminomethyl phosphate

aminomethyl phosphate

3,4,5-trimethoxybenzoic acid methyl ester
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%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4,5-trimethoxybenzoic acid methyl ester
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%
methanol
67-56-1

methanol

(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

3,4,5-trimethoxybenzoic acid methyl ester
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%
methanol
67-56-1

methanol

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

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

3,4,5-trimethoxybenzoic acid methyl ester
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%
N,N-dimethyl(3,4,5-trimethoxyphenyl)carboxamide
5658-49-1

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

trimethoxonium tetrafluoroborate
420-37-1

trimethoxonium tetrafluoroborate

3,4,5-trimethoxybenzoic acid methyl ester
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%
methylene chloride
74-87-3

methylene chloride

Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 10 - 35℃; for 3h; Temperature; Reagent/catalyst;85.9%
methylene chloride
74-87-3

methylene chloride

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 10 - 110℃; for 10h; Time;85.3%
methyl galloate
99-24-1

methyl galloate

methyl iodide
74-88-4

methyl iodide

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 58h;85%
With potassium carbonate In N,N-dimethyl-formamide at 85℃;78%
With potassium carbonate; acetone
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With copper quinolate In water; dimethyl sulfoxide at 120℃; for 24h;85%
methanol
67-56-1

methanol

3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methanol With sodium
Stage #2: 3,4,5-Trimethoxybenzoyl chloride In methanol at 20℃; for 5h;		83%
With triethylamine at 20℃;
at 25℃; Kinetics;
dimethylsulfone
67-71-0

dimethylsulfone

3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 1.5h;79%
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

methyl iodide
74-88-4

methyl iodide

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h;77%
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃;
With potassium carbonate In acetone at 60℃; for 5h;400 mg
methanol
67-56-1

methanol

(E)-3,4,5-trimethoxybenzaldehyde oxime
39201-89-3, 65567-36-4, 65567-39-7

(E)-3,4,5-trimethoxybenzaldehyde oxime

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With 2-nitrobenzeneseleninic acid; dihydrogen peroxide at 20℃; for 24h;71%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With pyridine at 0℃; for 0.333333h;70%
tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

Eudesmic acid
118-41-2

Eudesmic acid

Conditions
ConditionsYield
With potassium phosphate; copper quinolate; tetra-(n-butyl)ammonium iodide In water; dimethyl sulfoxide at 120℃; for 24h;A 70%
B n/a
...Expand
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

methyl iodide
74-88-4

methyl iodide

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

methyl 3,5-dihydroxy-4-methoxybenzoate
24093-81-0

methyl 3,5-dihydroxy-4-methoxybenzoate

C

3-hydroxy-4,5-dimethoxybenzoate
83011-43-2

3-hydroxy-4,5-dimethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;A 67%
B 7%
C 12%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;A 10%
B 61%
C 14%
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

methyl galloate
99-24-1

methyl galloate

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

methyl 3,5-dihydroxy-4-methoxybenzoate
24093-81-0

methyl 3,5-dihydroxy-4-methoxybenzoate

C

3-hydroxy-4,5-dimethoxybenzoate
83011-43-2

3-hydroxy-4,5-dimethoxybenzoate

Conditions
ConditionsYield
In ethanol; dichloromethane at 0℃;A n/a
B 54%
C n/a
In ethanol; dichloromethane at 0℃;A n/a
B 10%
C 40%
In ethanol; dichloromethane at 0℃; Yields of byproduct given;
...Expand
methyl 2-bromo-3,4,5-trimethoxybenzoate
1968-71-4

methyl 2-bromo-3,4,5-trimethoxybenzoate

methyl 6-bromo-2,3,4-trimethoxybenzoate
80141-07-7

methyl 6-bromo-2,3,4-trimethoxybenzoate

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

methyl 2,3,4-trimethoxybenzoate
6395-18-2

methyl 2,3,4-trimethoxybenzoate

C

dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate
1968-73-6

dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate

D

dimethyl 3,4,4',5,5',6'-hexamethoxybiphenyl-2,2'-dicarboxylate
80141-06-6

dimethyl 3,4,4',5,5',6'-hexamethoxybiphenyl-2,2'-dicarboxylate

Conditions
ConditionsYield
With copper bronze at 280℃; for 0.333333h; Further byproducts given;A 9%
B 7%
C 26%
D 46%
...Expand
methyl 2-bromo-3,4,5-trimethoxybenzoate
1968-71-4

methyl 2-bromo-3,4,5-trimethoxybenzoate

methyl 6-bromo-2,3,4-trimethoxybenzoate
80141-07-7

methyl 6-bromo-2,3,4-trimethoxybenzoate

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate
1968-73-6

dimethyl 3,3',4,4',5,5'-hexamethoxybiphenyl-2,2'-dicarboxylate

C

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester
4891-62-7, 65995-60-0, 71307-89-6

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester

D

dimethyl 3,4,4',5,5',6'-hexamethoxybiphenyl-2,2'-dicarboxylate
80141-06-6

dimethyl 3,4,4',5,5',6'-hexamethoxybiphenyl-2,2'-dicarboxylate

Conditions
ConditionsYield
With copper bronze 1.) from 240 deg C to 280 deg C, 2.) 280 deg C, 20 min; Further byproducts given;A 9%
B 26%
C 26%
D 46%
...Expand
methyl 2-iodo-3,4,5-tri-methoxybenzoate
214260-74-9

methyl 2-iodo-3,4,5-tri-methoxybenzoate

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester
4891-62-7, 65995-60-0, 71307-89-6

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester

C

4,5:4',5'-bis(methylenedioxy)-1,1'-biphenyl-2,2'-dicarboxaldehyde
60229-65-4

4,5:4',5'-bis(methylenedioxy)-1,1'-biphenyl-2,2'-dicarboxaldehyde

D

methyl 2-formyl-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxylate
73252-65-0

methyl 2-formyl-4,5-methylenedioxy-4',5',6'-trimethoxy-1,1'-biphenyl-2'-carboxylate

Conditions
ConditionsYield
With <2-cyclohexyliminomethyl-4,5-methylenedioxyphenyl-C,N>(triethyl phosphite)copper(I) In tetrahydrofuran; hexane at 25℃; for 96h; Further byproducts given;A 15%
B 15%
C 4%
D 34%
...Expand
methyl 2-bromo-3,4,5-trimethoxybenzoate
1968-71-4

methyl 2-bromo-3,4,5-trimethoxybenzoate

methyl 6-bromo-2,3,4-trimethoxybenzoate
80141-07-7

methyl 6-bromo-2,3,4-trimethoxybenzoate

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

methyl 2,3,4-trimethoxybenzoate
6395-18-2

methyl 2,3,4-trimethoxybenzoate

C

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester
4891-62-7, 65995-60-0, 71307-89-6

4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With copper bronze 1.) from 240 deg C to 280 deg C, 2.) 280 deg C, 20 min;A 9%
B 7%
C 26%
...Expand
methyl 3,5-dihydroxy-4-methoxybenzoate
24093-81-0

methyl 3,5-dihydroxy-4-methoxybenzoate

methyl iodide
74-88-4

methyl iodide

A

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

B

3-hydroxy-4,5-dimethoxybenzoate
83011-43-2

3-hydroxy-4,5-dimethoxybenzoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 55℃;A 12%
B n/a
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

methyl 3,5-dihydroxy-4-methoxybenzoate
24093-81-0

methyl 3,5-dihydroxy-4-methoxybenzoate

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

diazomethane
186581-53-3, 908094-01-9

diazomethane

Eudesmic acid
118-41-2

Eudesmic acid

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Conditions
ConditionsYield
With diethyl ether
In diethyl ether
In diethyl ether for 0.166667h;
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

methyl syringate
884-35-5

methyl syringate

Conditions
ConditionsYield
With iodine; magnesium In diethyl ether; dichloromethane at 80℃; for 1h;100%
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester With aluminum (III) chloride In dichloromethane at 20℃;
Stage #2: With hydrogenchloride; water In dichloromethane; chloroform		98%
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester With aluminum (III) chloride In dichloromethane at 20℃;
Stage #2: With hydrogenchloride In chloroform		98%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

3,4,5-trimethoxybenzohydrazide
3291-03-0

3,4,5-trimethoxybenzohydrazide

Conditions
ConditionsYield
With hydrazine at 92℃; for 4h;98.2%
With hydrazine In methanol; water Reflux;92%
With hydrazine hydrate In ethanol for 2h; Reflux;92%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

Eudesmic acid
118-41-2

Eudesmic acid

Conditions
ConditionsYield
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester With potassium hydroxide In ethanol; water for 3h; Reflux;
Stage #2: With sulfuric acid In water		95%
With potassium hydroxide In ethanol for 48h; Reflux;95.6%
With potassium hydroxide In ethanol for 48h; Reflux;95.6%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

Conditions
ConditionsYield
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 110℃; under 22502.3 Torr; for 24h; Inert atmosphere; Autoclave;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.166667h; Inert atmosphere;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h;88%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

methyl 2-bromo-3,4,5-trimethoxybenzoate
1968-71-4

methyl 2-bromo-3,4,5-trimethoxybenzoate

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 20℃; for 4h; Inert atmosphere;95%
With bromine In chloroform84%
With bromine; acetic anhydride at 0 - 20℃; for 5h;82%
difluoromethyl phenyl sulfide
1535-67-7

difluoromethyl phenyl sulfide

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

methyl 2-formyl-3,4,5-trimethoxybenzoate
72326-99-9

methyl 2-formyl-3,4,5-trimethoxybenzoate

Conditions
ConditionsYield
Stage #1: difluoromethyl phenyl sulfide; 3,4,5-trimethoxybenzoic acid methyl ester With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 20℃; for 2h; Reagent/catalyst; Time;		95%
1-indoline
496-15-1

1-indoline

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

indolin-1-yl(3,4,5-trimethoxyphenyl)methanone
313496-16-1

indolin-1-yl(3,4,5-trimethoxyphenyl)methanone

Conditions
ConditionsYield
With C18H15IMnN3O3; sodium t-butanolate In toluene at 120℃; for 18h; Catalytic behavior; Time; Inert atmosphere; Schlenk technique;95%
With bis(1,5-cyclooctadiene)nickel (0); 3,4,7,8-Tetramethyl-o-phenanthrolin; potassium tert-butylate In toluene at 140℃; for 16h;89%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

(E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine
358723-67-8

(E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine

1-phenyl-3-(2-phenylethenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazole

1-phenyl-3-(2-phenylethenyl)-5-(3,4,5-trimethoxyphenyl)-1H-pyrazole

Conditions
ConditionsYield
Stage #1: (E)-1-phenyl-2-((E)-4-phenylbut-3-en-2-ylidene)hydrazine With lithium diisopropyl amide In tetrahydrofuran at 0℃;
Stage #2: 3,4,5-trimethoxybenzoic acid methyl ester In tetrahydrofuran at 0℃;		93%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

5-hydroxy(2H2)methyl-1,2,3-trimethoxybenzene
478703-05-8

5-hydroxy(2H2)methyl-1,2,3-trimethoxybenzene

Conditions
ConditionsYield
With lithium aluminium deuteride In diethyl ether for 4h; Heating;87%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

1-phenyl-2-phenylacetylhydrazine
6596-66-3

1-phenyl-2-phenylacetylhydrazine

1,2-dihydro-1,4-diphenyl-5-(3,4,5-trimethoxyphenyl)-3H-pyrazol-3-one

1,2-dihydro-1,4-diphenyl-5-(3,4,5-trimethoxyphenyl)-3H-pyrazol-3-one

Conditions
ConditionsYield
Stage #1: 1-phenyl-2-phenylacetylhydrazine With lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 2h;
Stage #2: 3,4,5-trimethoxybenzoic acid methyl ester In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexane for 1h; Heating;		86%
Dichloromethyl methyl ether
4885-02-3

Dichloromethyl methyl ether

3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

methyl 2-formyl-3,4,5-trimethoxybenzoate
72326-99-9

methyl 2-formyl-3,4,5-trimethoxybenzoate

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -20 - 20℃; for 12.5h; Inert atmosphere;85%
With tin(IV) chloride In dichloromethane at -70 - 5℃; for 2h; Inert atmosphere;5.28 g
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

methyl 2-iodo-3,4,5-tri-methoxybenzoate
214260-74-9

methyl 2-iodo-3,4,5-tri-methoxybenzoate

Conditions
ConditionsYield
With iodine; silver trifluoroacetate In chloroform at 20℃; for 2.06667h;84%
With iodine; periodic acid In sulfuric acid; acetic acid72%
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

boron trifluoride
7637-07-2

boron trifluoride

acetophenone
98-86-2

acetophenone

C18H17BF2O5

C18H17BF2O5

Conditions
ConditionsYield
Stage #1: 3,4,5-trimethoxybenzoic acid methyl ester; acetophenone With sodium hydride In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;
Stage #2: boron trifluoride With triethylamine In diethyl ether; dichloromethane at 20℃; for 1h; Inert atmosphere;		83%
...Expand
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

3,4,5-trimethoxy-2-nitrobenzoic acid methyl ester
5081-42-5

3,4,5-trimethoxy-2-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
With (NH4)2Ce(NO3)5; acetic anhydride at 60℃; for 2h;82%
With nitric acid; acetic acid at 50℃; for 1.5h; Inert atmosphere;38%
With nitric acid In acetic acid at 10 - 30℃;26%

Methyl 3,4,5-trimethoxybenzoate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl 3,4,5-trimethoxybenzoate 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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