Product Name

  • Name

    3,4,5-Trimethoxyphenylacetonitrile

  • EINECS 236-388-5
  • CAS No. 13338-63-1
  • Article Data36
  • CAS DataBase
  • Density 1.104 g/cm3
  • Solubility Insoluble in water
  • Melting Point 76-79 ºC
  • Formula C11H13 N O3
  • Boiling Point 327.9 °C at 760 mmHg
  • Molecular Weight 207.229
  • Flash Point 132.8 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety S24/25
  • Risk Codes R20/21/22   
  • Molecular Structure Molecular Structure of 13338-63-1 (3,4,5-Trimethoxyphenylacetonitrile)
  • Hazard Symbols
  • Synonyms Acetonitrile,(3,4,5-trimethoxyphenyl)- (6CI,7CI,8CI); (3,4,5-Trimethoxyphenyl)acetonitrile;2-(3,4,5-Trimethoxyphenyl)acetonitrile; 3,4,5-Trimethoxybenzeneacetonitrile;3,4,5-Trimethoxybenzyl cyanide; 3,4,5-Trimethoxybenzylnitrile; NSC 97556
  • PSA 51.48000
  • LogP 1.77848

Synthetic route

Oxime of 3,4,5-trimethoxyphenylpyruvic acid
139109-56-1

Oxime of 3,4,5-trimethoxyphenylpyruvic acid

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With 1,1'-oxalyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;88%
With acetic anhydride
With acetic anhydride for 0.0833333h; Heating;
3,4,5-trimethoxyphenyl acetic acid
951-82-6

3,4,5-trimethoxyphenyl acetic acid

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 50h;88%
sodium cyanide
773837-37-9

sodium cyanide

5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 36h;85%
In acetonitrile Reflux;
In acetonitrile for 4h; Reflux;
In dimethyl sulfoxide
2,3,4-trimethoxybromobenzene
10385-36-1

2,3,4-trimethoxybromobenzene

acetonitrile
75-05-8

acetonitrile

A

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

B

Bis-(3,4,5-trimethoxy-phenyl)-acetonitrile
36764-81-5

Bis-(3,4,5-trimethoxy-phenyl)-acetonitrile

Conditions
ConditionsYield
With ethoxyethoxyethanol; sodium amide In 1,2-dimethoxyethane 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 4.5 h;A 83%
B 11%
...Expand
3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

sodium cyanide
143-33-9

sodium cyanide

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide Ambient temperature;75%
3,4,5-trimethoxybenzoyl cyanide
5955-75-9

3,4,5-trimethoxybenzoyl cyanide

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With sodium sulfate; ethanethiol; zinc(II) chloride weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol;
(3,4,5-trimethoxy-phenyl)-acetaldehyde-oxime

(3,4,5-trimethoxy-phenyl)-acetaldehyde-oxime

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With acetic anhydride
Oxime of 3,4,5-trimethoxyphenylpyruvic acid
139109-56-1

Oxime of 3,4,5-trimethoxyphenylpyruvic acid

acetic anhydride
108-24-7

acetic anhydride

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

potassium cyanide
151-50-8

potassium cyanide

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

3,4,5-trimethoxy-benzaldehyde

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With water; chloroformic acid ethyl ester; magnesium sulfate Hydrieren des Reaktionsprodukts an Palladium in Benzol;
2,3,4-trimethoxybromobenzene
10385-36-1

2,3,4-trimethoxybromobenzene

acetonitrile
75-05-8

acetonitrile

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With sodium amide 1.) liquid ammonia, 5 min, 2.) liquid ammonia, 15 min; Yield given. Multistep reaction;
potassium cyanide
151-50-8

potassium cyanide

5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
In 1,4-dioxane; water Heating;
4-hydroxy-3,5-dimethoxyphenylacetonitrile
42973-55-7

4-hydroxy-3,5-dimethoxyphenylacetonitrile

dimethyl sulfate
77-78-1

dimethyl sulfate

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With potassium carbonate In acetone
sodium cyanide
143-33-9

sodium cyanide

5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With sodium iodide
potassium cyanide
151-50-8

potassium cyanide

<3,4,5-trimethoxy-benzyl chloride

<3,4,5-trimethoxy-benzyl chloride

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With methanol
With methanol
With ethanol
tetraethylammoniumcyanide
13435-20-6

tetraethylammoniumcyanide

5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃;
(3,4,5-trimethoxyphenyl)methanol
3840-31-1

(3,4,5-trimethoxyphenyl)methanol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2 / dioxane / 20 °C
2: acetonitrile / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp.
2: 75 percent / dimethylsulfoxide / Ambient temperature
View Scheme
Multi-step reaction with 5 steps
1: pyridinium chlorochromate / CH2Cl2 / 3 h
2: sodium acetate / acetic anhydride / Heating
3: NaOH / H2O / Heating
4: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C
5: acetic anhydride / 0.08 h / Heating
View Scheme
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4 / methanol / 20 °C
2: SOCl2 / dioxane / 20 °C
3: acetonitrile / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: sodium acetate / acetic anhydride / Heating
2: NaOH / H2O / Heating
3: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C
4: acetic anhydride / 0.08 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; methanol / tetrahydrofuran / 2 h / 0 °C
2: thionyl chloride / dichloromethane / 1.5 h / 20 °C
3: dimethyl sulfoxide / 36 h / 20 °C
View Scheme
3,4,5-trimethoxybenzoic acid methyl ester
1916-07-0

3,4,5-trimethoxybenzoic acid methyl ester

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / LAH / tetrahydrofuran
2: 80 percent / PBr3, triethylamine / CCl4 / 1) 1h, 0 degC 2) 3h, roomtemp.
3: 75 percent / dimethylsulfoxide / Ambient temperature
View Scheme
Multi-step reaction with 6 steps
1: lithium aluminium hydride / diethyl ether / 3 h / Heating
2: pyridinium chlorochromate / CH2Cl2 / 3 h
3: sodium acetate / acetic anhydride / Heating
4: NaOH / H2O / Heating
5: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C
6: acetic anhydride / 0.08 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: LiAlH4 / diethyl ether
2: HCl / benzene / 0 °C
3: dioxane; H2O / Heating
View Scheme
3-(3,4,5-trimethoxyphenyl)pyruvic acid
61404-52-2

3-(3,4,5-trimethoxyphenyl)pyruvic acid

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C
2: acetic anhydride / 0.08 h / Heating
View Scheme
2-Phenyl-4-(3',4',5'-trimethoxybenzylidene)oxazolone
62616-09-5

2-Phenyl-4-(3',4',5'-trimethoxybenzylidene)oxazolone

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOH / H2O / Heating
2: hydroxylamine hydrochloride / aq. NaOH / 0.5 h / 60 °C
3: acetic anhydride / 0.08 h / Heating
View Scheme
3,4,5-Trimethoxybenzoyl chloride
4521-61-3

3,4,5-Trimethoxybenzoyl chloride

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: ethanethiol; ZnCl2; Na2SO4 / weiteres Reagens: Benzol; Erwaermen des Reaktionsprodukts mit Raney-Nickel in wss. Methanol
View Scheme
elemicin
487-11-6

elemicin

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ozone; ethyl acetate; oxygen / -15 °C / und anschliessende Hydrierung an Palladium/Calciumcarbonat unter Kuehlung; Isolierung als Natriumhydrogensulfit-Addukt
3: acetic acid anhydride
View Scheme
3,4,5-trimethoxyphenylacetaldehyde
5320-31-0

3,4,5-trimethoxyphenylacetaldehyde

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: acetic acid anhydride
View Scheme
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: H2O
2: dimethylformamide
3: K2CO3 / acetone
View Scheme
2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol
39667-14-6

2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylformamide
2: K2CO3 / acetone
View Scheme
5-(chloromethyl)-1,2,3-trimethoxybenzene
3840-30-0

5-(chloromethyl)-1,2,3-trimethoxybenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
In water; ethyl acetate; N,N-dimethyl-formamide
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3,4,5-trimethoxybenzyl bromide
21852-50-6

3,4,5-trimethoxybenzyl bromide

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In acetonitrile Reflux;
With tetra-n-butylammoniumfluoride trihydrate In acetonitrile for 6h; Reflux;
With tetrabutyl ammonium fluoride In acetonitrile for 6h; Reflux;
With tetrabutyl ammonium fluoride In acetonitrile for 6h; Reflux;
3,4,5-trihydroxybenzoic acid
149-91-7

3,4,5-trihydroxybenzoic acid

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
3: phosphorus tribromide / dichloromethane / 4 h / Cooling with ice; Inert atmosphere
4: tetra-n-butylammoniumfluoride trihydrate / acetonitrile / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
3: phosphorus tribromide / dichloromethane / 0 - 20 °C
4: tetrabutyl ammonium fluoride / acetonitrile / Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 4.5 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
4: tetrabutyl ammonium fluoride / acetonitrile / 6 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetone / 4.5 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere; Cooling with ice
3: phosphorus tribromide / dichloromethane / 4 h / Inert atmosphere; Cooling with ice
4: tetrabutyl ammonium fluoride / acetonitrile / 6 h / Reflux
View Scheme
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

formic acid ethyl ester
109-94-4

formic acid ethyl ester

3-hydroxy-2-(3,4,5-trimethoxyphenyl)acrylonitrile sodium salt

3-hydroxy-2-(3,4,5-trimethoxyphenyl)acrylonitrile sodium salt

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Heating;98%
4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

C21H25NO3

C21H25NO3

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;98%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

C18H17NO4

C18H17NO4

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20 - 85℃; for 3h; Inert atmosphere;97%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

hexan-1-ol
111-27-3

hexan-1-ol

2-(3,4,5-Trimethoxy-phenyl)-octanenitrile
108781-06-2

2-(3,4,5-Trimethoxy-phenyl)-octanenitrile

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;97%
3-(pyridin-2-yl)-propanol
2859-68-9

3-(pyridin-2-yl)-propanol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

C19H22N2O3

C19H22N2O3

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;96%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Diphenylphosphine oxide
4559-70-0

Diphenylphosphine oxide

(3,4,5-trimethoxybenzyl)diphenylphosphine oxide
159386-48-8

(3,4,5-trimethoxybenzyl)diphenylphosphine oxide

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium tert-butylate; 2'-(di-tert-butylphosphanyl)-N,N-dimethyl-[1,1'-biphenyl]-2-amine In 1,4-dioxane at 120℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Schlenk technique;96%
With potassium tert-butylate; nickel dichloride In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; Schlenk technique;71%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

O-methoxymethylisovanillin
5779-98-6

O-methoxymethylisovanillin

(Z)-3-(4-Methoxy-3-methoxymethoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-acrylonitrile

(Z)-3-(4-Methoxy-3-methoxymethoxy-phenyl)-2-(3,4,5-trimethoxy-phenyl)-acrylonitrile

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In dichloromethane for 4h; Ambient temperature;95%
3-iodo-4-methoxybenzaldehyde
2314-37-6

3-iodo-4-methoxybenzaldehyde

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

C19H18INO4
1408251-07-9

C19H18INO4

Conditions
ConditionsYield
With sodium methylate In methanol at 45℃;93%
p-methylcyclohexanol
589-91-3

p-methylcyclohexanol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

C18H23NO3

C18H23NO3

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 10h; Inert atmosphere; Green chemistry;93%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

3,4,5-trimethoxyphenyl acetic acid
951-82-6

3,4,5-trimethoxyphenyl acetic acid

Conditions
ConditionsYield
With potassium hydroxide Heating;92%
With sulfuric acid; acetic acid In water for 22h; Reflux;82%
With hydrogenchloride
With potassium hydroxide In ethanol Reflux;
With water; potassium hydroxide In ethanol for 15h; Reflux;
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

3-(2,3,4-trimethoxyphenyl)-[1,8]naphthyridin-2-ylamine
1075240-58-2

3-(2,3,4-trimethoxyphenyl)-[1,8]naphthyridin-2-ylamine

Conditions
ConditionsYield
With aminosulfonic acid for 0.05h; microwave irradiation;92%
ethanol
64-17-5

ethanol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

Ethyl 3,4,5-Trimethoxyphenylacetimidate Hydrochloride
93270-42-9

Ethyl 3,4,5-Trimethoxyphenylacetimidate Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride Ambient temperature;91%
With hydrogenchloride In benzene82%
With hydrogenchloride In chloroform for 2h; Ambient temperature;
With hydrogenchloride In diethyl ether at 0℃;
With hydrogenchloride In diethyl ether
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

cyclohexanone
108-94-1

cyclohexanone

(1-hydroxy-cyclohexyl)-(3,4,5-trimethoxy-phenyl)-acetonitrile

(1-hydroxy-cyclohexyl)-(3,4,5-trimethoxy-phenyl)-acetonitrile

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 0 - 15℃; for 1h;90%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

(Z)-2-(3,4,5-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)acrylonitrile

(Z)-2-(3,4,5-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)acrylonitrile

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 85℃; for 1h; Knoevenagel Condensation; Inert atmosphere;90%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

ethyl 3,4,5,-trimethoxy-α-cyanobenzeneacetate
62038-54-4

ethyl 3,4,5,-trimethoxy-α-cyanobenzeneacetate

Conditions
ConditionsYield
89%
89%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

dimethyl sulfate
77-78-1

dimethyl sulfate

2-methyl-2-(3,4,5-trimethoxyphenyl)propanenitrile
19589-24-3

2-methyl-2-(3,4,5-trimethoxyphenyl)propanenitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -30 - 20℃;88%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

(4-ethoxyphenyl)boronic acid
22237-13-4

(4-ethoxyphenyl)boronic acid

1-(4-ethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one

1-(4-ethoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;87%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

3-fluoro-4-methoxy-phenylboronic acid
149507-26-6

3-fluoro-4-methoxy-phenylboronic acid

1-(3-fluoro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

1-(3-fluoro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;85%
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

(Z)-4-(o-tolyl)-2-(3,4,5-trimethoxyphenyl)but-2-enenitrile

(Z)-4-(o-tolyl)-2-(3,4,5-trimethoxyphenyl)but-2-enenitrile

Conditions
ConditionsYield
With potassium tert-butylate; tert-butyl alcohol In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; stereoselective reaction;84%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

1-(p-tolyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

1-(p-tolyl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;84%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

1-(naphthalen-2-yl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

1-(naphthalen-2-yl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;84%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

cyclohexanol
108-93-0

cyclohexanol

C17H21NO3

C17H21NO3

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 10h; Inert atmosphere; Green chemistry;83%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

(E)-3,4,4',5-tetramethoxystilbene
134029-62-2

(E)-3,4,4',5-tetramethoxystilbene

Conditions
ConditionsYield
With C15H25Cl2N3NiO3; potassium tert-butylate In octane at 120℃; for 24h; Schlenk technique; Inert atmosphere;83%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(Z)-2-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile

(Z)-2-(3,4,5-trimethoxyphenyl)-3-(4-methoxyphenyl)acrylonitrile

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; Reflux;82%
With sodium hydroxide; Aliquat 336 In dichloromethane for 4h; Ambient temperature;75%
Stage #1: 2-(3,4,5-trimethoxyphenyl)acetonitrile; 4-methoxy-benzaldehyde In methanol at 60℃; for 0.5h;
Stage #2: With sodium methylate In methanol at 60℃;
methanol
67-56-1

methanol

2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

α-methyl-3,4,5-trimethoxybenzeneacetonitrile
91641-41-7

α-methyl-3,4,5-trimethoxybenzeneacetonitrile

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;82%
2-(3,4,5-trimethoxyphenyl)acetonitrile
13338-63-1

2-(3,4,5-trimethoxyphenyl)acetonitrile

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one
203058-56-4

1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethane-1-one

Conditions
ConditionsYield
With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere; Schlenk technique;82%

3,4,5-Trimethoxyphenylacetonitrile Chemical Properties

Molecular Formula:C11H13NO3
Molar mass:207.2258g/mol
Structure of 3,4,5-Trimethoxyphenylacetonitrile(13338-63-1):
                           
Synonyms:3,4,5-Trimethoxybenzyl cyanide;3,4,5-Trimethoxybenzylnitrile;3,4,5-Trimethoxybenzeneacetonitrile;Benzeneacetonitrile, 3,4,5-trimethoxy-;3,4,5-Trimethoxyphenylacetylnitryl
Density:1.104 g/cm3     
Flash Point:132.8 °C      
Boiling Point:327.9 °C at 760 mmHg     
Index of Refraction:1.506      
Vapour Pressure:0.000196 mmHg at 25°C     
Melting point:77-79 °C(lit.)

3,4,5-Trimethoxyphenylacetonitrile Uses

3,4,5-Trimethoxyphenylacetonitrile(13338-63-1) can be used as API intermediates.

3,4,5-Trimethoxyphenylacetonitrile Toxicity Data With Reference

1.mouse LD50 intravenous 56mg/kg (56mg/kg)  
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04092.
2.Carcinogenicity:3,4,5-Trimethoxyphenylacetonitrile(13338-63-1)- Not listed as a carcinogen by  NTP, IARC,ACGIH, or CA Prop 65. 
Other: The toxicological properties have not been fully investigated.You can see actual entry in RTECS for complete information.

3,4,5-Trimethoxyphenylacetonitrile Safety Profile

Hazard Codes:Xn
Risk Statements:
20:  Harmful by inhalation
21:  Harmful in contact with skin
22:  Harmful if swallowed 
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
24:  Avoid contact with skin
25:  Avoid contact with eyes
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:  Wear suitable protective clothing

3,4,5-Trimethoxyphenylacetonitrile Specification

Stability and Reactivity of 3,4,5-Trimethoxyphenylacetonitrile(13338-63-1):
Conditions to Avoid:Incompatible materials. 
Incompatibilities with Other Materials:Strong acids , strong bases,strong oxidizing agents.
Hazardous Decomposition Products: Hydrogen cyanide,carbon dioxide,nitrogen oxides,  carbon monoxide.

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