Product Name

  • Name

    3,5-Dimethoxyaniline

  • EINECS 233-616-5
  • CAS No. 10272-07-8
  • Article Data36
  • CAS DataBase
  • Density 1.096 g/cm3
  • Solubility insoluble in water
  • Melting Point 54-57 ºC
  • Formula C8H11NO2
  • Boiling Point 178 ºC (20 mmHg)
  • Molecular Weight 153.181
  • Flash Point 135 ºC
  • Transport Information UN 2811
  • Appearance White crystal or Colorless liquid
  • Safety 26-36-36/37/39-22
  • Risk Codes 22-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 10272-07-8 (3,5-Dimethoxyaniline)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms 3,5-Dimethoxy-phenylamine;3,5-Dimethoxybenzeneamine;Benzenamine, 3,5-dimethoxy-;3,5-dimethoxy aniline;5-Aminoresorcinol dimethylether;
  • PSA 44.48000
  • LogP 1.86720

Synthetic route

1-azido-3,5-dimethoxybenzene
85862-68-6

1-azido-3,5-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With sodium tetrahydroborate; palladium In water for 1.5h; Inert atmosphere;99%
With sodium sulfide; water for 0.5h; Reflux;96%
With ammonium hydroxide at 90℃; for 0.5h;90%
With triethylamine; tris[tert-butyl]phosphonium tetrafluoroborate In tetrahydrofuran; water at 20℃; for 15h; Staudinger Azide Reduction;94 %Spectr.
N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
85657-94-9

N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With water; potassium carbonate In methanol for 20h; Ambient temperature;94%
2-Trimethylsilanyl-ethanesulfonic acid (3,5-dimethoxy-phenyl)-amide
106018-88-6

2-Trimethylsilanyl-ethanesulfonic acid (3,5-dimethoxy-phenyl)-amide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With cesium fluoride In N,N-dimethyl-formamide at 95℃; for 40h;93%
1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;93%
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere;88%
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere; Schlenk technique;88%
N-(3,5-dimethoxy-phenyl)-acetamide
79257-61-7

N-(3,5-dimethoxy-phenyl)-acetamide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Stage #1: N-(3,5-dimethoxy-phenyl)-acetamide With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere;
Stage #2: With water In tetrahydrofuran Inert atmosphere; chemoselective reaction;
86%
With alkaline solution
3,5-dimethoxyphenylboronic acid
192182-54-0

3,5-dimethoxyphenylboronic acid

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;82%
1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Stage #1: 1-bromo-3,5-dimethoxybenzene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;
78%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Sealed tube;68%
With ammonia; sodium; ferric nitrate
1-iodo-3,5-dimethoxybenzene
25245-27-6

1-iodo-3,5-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube;75%
3,5-dimethoxyphenol
500-99-2

3,5-dimethoxyphenol

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Stage #1: 3,5-dimethoxyphenol With Nonafluorobutanesulfonyl fluoride; tris(trimethylsilyl)amine; potassium hexamethylsilazane In tetrahydrofuran at 60℃; for 5h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water at 20℃; for 0.0833333h; pH=3 - 4; Reagent/catalyst; Solvent;
75%
3,5-dimethoxybenzoic acid
1132-21-4

3,5-dimethoxybenzoic acid

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Stage #1: 3,5-dimethoxybenzoic acid With diphenylphosphoranyl azide; triethylamine In toluene at 80℃;
Stage #2: With sodium hydroxide In tetrahydrofuran; toluene at 20℃; for 2h;
43%
Stage #1: 3,5-dimethoxybenzoic acid With diphenylphosphoranyl azide; triethylamine In toluene at 80℃;
Stage #2: With sodium hydroxide In tetrahydrofuran for 2h;
43%
N-hydroxy-3,5-dimethoxybenzamide
710311-79-8

N-hydroxy-3,5-dimethoxybenzamide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Stage #1: N-hydroxy-3,5-dimethoxybenzamide With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 2h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃;
3%
Stage #1: N-hydroxy-3,5-dimethoxybenzamide With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h;
1-Bromo-2,4-dimethoxybenzene
17715-69-4

1-Bromo-2,4-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With ammonia; sodium amide in fluessiges NH3;
1,3-dimethoxy-5-nitrobenzene
16147-07-2

1,3-dimethoxy-5-nitrobenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With hydrogenchloride; tin
With hydrogenchloride; tin; tin(ll) chloride at 40℃; Reagens 5: Essigsaeure;
With ethanol; nickel Hydrogenation;
With hydrogen; palladium on activated charcoal In ethyl acetate
3,5-dimethoxybenzamide
17213-58-0

3,5-dimethoxybenzamide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With sodium hypobromide at -15℃;
Yield given;
With sodium hypochlorite; sodium hydroxide at 80℃; for 5h;4.1 g
ethyl 3,5-dimethoxybenzoate
17275-82-0

ethyl 3,5-dimethoxybenzoate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 78 percent / hydrazine hydrate / 2 h / Heating
2: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C
3: 93 percent / toluene / 2.5 h / Heating
4: 8.7 g / sodium hydroxide (20percent) / 60 °C
View Scheme
3,5-Dihydroxybenzoic acid
99-10-5

3,5-Dihydroxybenzoic acid

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 84 percent / sodium hydroxide / heating
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 55 °C
2.1: triethylamine; diphenylphosphoranyl azide / toluene / 80 °C
2.2: 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetone / 55 °C
2.1: triethylamine; diphenylphosphoranyl azide / toluene / 80 °C
2.2: 2 h
View Scheme
azido(3,5-dimethoxyphenyl)methanone
75996-26-8

azido(3,5-dimethoxyphenyl)methanone

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 93 percent / toluene / 2.5 h / Heating
2: 8.7 g / sodium hydroxide (20percent) / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: CH2Cl2 / 60 h / Heating
2: 94 percent / H2O, K2CO3 / methanol / 20 h / Ambient temperature
View Scheme
3,5-dimethoxy-benzoic acid hydrazide
51707-38-1

3,5-dimethoxy-benzoic acid hydrazide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 63 percent / sodium nitrite, hydrochloric acid (2M), acetic acid (glacial) / H2O / 1 h / -10 °C
2: 93 percent / toluene / 2.5 h / Heating
3: 8.7 g / sodium hydroxide (20percent) / 60 °C
View Scheme
3,5-dimethoxybenzoyl chloride
17213-57-9

3,5-dimethoxybenzoyl chloride

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

3,5-dimethoxyphenyl isocyanate
54132-76-2

3,5-dimethoxyphenyl isocyanate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 8.7 g / sodium hydroxide (20percent) / 60 °C
View Scheme
With benzoic acid; sodium hydroxide In tetrahydrofuran at 20℃; for 0.5h; Curtius Rearrangement;
3,5-dihydroxyphenylamine
20734-67-2

3,5-dihydroxyphenylamine

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous dioxane
2: aqueous NaOH
3: aq.-ethanolic alkaline solution
View Scheme
N-(3,5-dihydroxyphenyl)acetamide
73164-69-9

N-(3,5-dihydroxyphenyl)acetamide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous NaOH
2: aq.-ethanolic alkaline solution
View Scheme
methyl 3,5-dimethoxybenzoate
2150-37-0

methyl 3,5-dimethoxybenzoate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: liquid ammonia
2: aqueous sodium hypobromite / -15 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / 1,4-dioxane / 5 h / 20 °C
2: triethylamine; diphenyl phosphoryl azide / 80 °C
3: sodium hydroxide; benzoic acid / tetrahydrofuran / 0.5 h / 20 °C
View Scheme
3,5-dimethoxyphenol
500-99-2

3,5-dimethoxyphenol

ammonium chloride (NH4Cl)

ammonium chloride (NH4Cl)

2,3-dimethoxyphenol
5150-42-5

2,3-dimethoxyphenol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran
1-carbomethoxy-3,5-dihydroxybenzene
2150-44-9

1-carbomethoxy-3,5-dihydroxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate / acetonitrile / 20 °C
2: sodium hydroxide / 1,4-dioxane / 5 h / 20 °C
3: triethylamine; diphenyl phosphoryl azide / 80 °C
4: sodium hydroxide; benzoic acid / tetrahydrofuran / 0.5 h / 20 °C
View Scheme
1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

A

bis(3,5-dimethoxyphenyl)amine
1445972-42-8

bis(3,5-dimethoxyphenyl)amine

B

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; Overall yield = 81 %;
C15H23NO3

C15H23NO3

A

heptanamide
628-62-6

heptanamide

B

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Conditions
ConditionsYield
With phosphoric acid; ammonia In ethylene glycol at 145℃; for 5h;A 95 %Spectr.
B 84 %Spectr.
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

(3,5-dimethoxyphenyl)-carbamic acid tert-butyl ester
384793-29-7

(3,5-dimethoxyphenyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; Inert atmosphere;100%
Stage #1: 3.5-dimethoxyaniline With triethylamine In dichloromethane at 20℃;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃;
99%
at 90℃; for 3h;98%
methyl chloroformate
79-22-1

methyl chloroformate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

methyl N-(3,5-dimethoxyphenyl)carbamate
83015-12-7

methyl N-(3,5-dimethoxyphenyl)carbamate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;94%
In toluene for 2h; Acylation; Heating;81%
4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline
190728-25-7

4-((6,7-dimethoxyquinolin-4-yl)oxy)aniline

bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

sodium hydrogencarbonate
144-55-8

sodium hydrogencarbonate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-(3,5-Dimethoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

N-(3,5-Dimethoxyphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

Conditions
ConditionsYield
With triethylamine In toluene100%
3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

Methacryloyl chloride
920-46-7

Methacryloyl chloride

N-(3,5-dimethoxyphenyl)-2-methylacrylamide
134354-28-2

N-(3,5-dimethoxyphenyl)-2-methylacrylamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
In dichloromethane at 0 - 20℃;
In dichloromethane at 0 - 20℃;
In dichloromethane at 0 - 20℃;
With dmap; triethylamine In dichloromethane at 0 - 20℃;
2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

2-bromo-N-(3,5-dimethoxyphenyl)acetamide

2-bromo-N-(3,5-dimethoxyphenyl)acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1.25h; Inert atmosphere;100%
at -77℃;
4-(prop-2-yn-1-ylcarbamoyl)benzoic acid

4-(prop-2-yn-1-ylcarbamoyl)benzoic acid

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

4-(3,5-dimethoxyphenylaminocarbonyl)-N-(prop-2-yn-1-yl)benzamide

4-(3,5-dimethoxyphenylaminocarbonyl)-N-(prop-2-yn-1-yl)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;99.9%
1,1,1-trifluoro-4-phenylbut-3-yn-2-one
58518-08-4

1,1,1-trifluoro-4-phenylbut-3-yn-2-one

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

(Z)-4-(3,5-Dimethoxy-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one
129633-19-8

(Z)-4-(3,5-Dimethoxy-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

Conditions
ConditionsYield
In methanol Ambient temperature;99%
2-bromo-4'-fluoroacetophenone
403-29-2

2-bromo-4'-fluoroacetophenone

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

2-[(3,5-dimethoxyphenyl)amino]-1-(4-fluorophenyl)ethanone
161139-70-4

2-[(3,5-dimethoxyphenyl)amino]-1-(4-fluorophenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In neat (no solvent) at 20℃; for 2h;99%
With sodium hydrogencarbonate In ethanol for 4h; Heating;
(Z)-ethyl 3-(methylamino)-3-phenylacrylate
81051-55-0, 53256-20-5

(Z)-ethyl 3-(methylamino)-3-phenylacrylate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

(Z)-3-(3,5-Dimethoxy-phenylamino)-3-phenyl-acrylic acid ethyl ester

(Z)-3-(3,5-Dimethoxy-phenylamino)-3-phenyl-acrylic acid ethyl ester

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane for 30h; Heating;99%
2-formylphenyl triflate
84761-77-3

2-formylphenyl triflate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

1,3-dimethoxyacridine
111043-16-4

1,3-dimethoxyacridine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; XPhos In toluene at 105℃; for 13h; Mechanism; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;99%
acetone
67-64-1

acetone

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-isopropyl-3,5-dimethoxyaniline
108103-33-9

N-isopropyl-3,5-dimethoxyaniline

Conditions
ConditionsYield
With acetic acid; zinc at 20 - 60℃; for 2.5h;99%
2-bromo-5-chlorobenzaldehyde
174265-12-4

2-bromo-5-chlorobenzaldehyde

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

7-chloro-1,3-dimethoxyacridine

7-chloro-1,3-dimethoxyacridine

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromo-5-chlorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere;
99%
2-bromo-5-nitrobenzaldehyde
84459-32-5

2-bromo-5-nitrobenzaldehyde

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

1,3-dimethoxy-7-nitroacridine

1,3-dimethoxy-7-nitroacridine

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromo-5-nitrobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere;
99%
2-bromo-6-fluorobenzaldehyde
360575-28-6

2-bromo-6-fluorobenzaldehyde

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

8-fluoro-1,3-dimethoxyacridine

8-fluoro-1,3-dimethoxyacridine

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-bromo-6-fluorobenzaldehyde In toluene at 80℃; for 12h; Inert atmosphere;
99%
ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

1,3-dimethoxyacridine
111043-16-4

1,3-dimethoxyacridine

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In toluene at 80℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere;
99%
Stage #1: 3.5-dimethoxyaniline With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: ortho-bromobenzaldehyde In toluene at 80℃; for 12h; Reagent/catalyst;
99%
1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

tris(3,5-dimethoxyphenyl)amine

tris(3,5-dimethoxyphenyl)amine

Conditions
ConditionsYield
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Schlenk technique;99%
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 60℃; for 19h; Inert atmosphere;81%
With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II); sodium t-butanolate In tetrahydrofuran at 60℃; Inert atmosphere;75%
3,5-dimethoxyaniline hydrochloride
40891-33-6

3,5-dimethoxyaniline hydrochloride

4,4'-dimethoxybenzoin
119-52-8

4,4'-dimethoxybenzoin

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

4,6-dimethoxy-2,3-di(4-methoxyphenyl)indole

4,6-dimethoxy-2,3-di(4-methoxyphenyl)indole

Conditions
ConditionsYield
at 130 - 140℃; for 1h;99%
ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate
869294-86-0

ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-(3,5-dimethoxyphenyl)-4-oxo-6-iodo-3,4-dihydroquinazoline-2-carboxamide

N-(3,5-dimethoxyphenyl)-4-oxo-6-iodo-3,4-dihydroquinazoline-2-carboxamide

Conditions
ConditionsYield
Stage #1: 3.5-dimethoxyaniline With trimethylaluminum In n-heptane; 1,2-dichloro-ethane at 0 - 20℃; for 0.5h;
Stage #2: ethyl 6-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate In n-heptane; 1,2-dichloro-ethane for 2h; Reflux;
99%
7-nitro-4-chloro-1H-indole-2-carboxylic acid ethyl ester

7-nitro-4-chloro-1H-indole-2-carboxylic acid ethyl ester

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

4-((3,5-dimethoxyphenyl)amino)-7-nitro-1H-indole-2-carboxylic acid ethyl ester

4-((3,5-dimethoxyphenyl)amino)-7-nitro-1H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; toluene for 4h; Reflux; Inert atmosphere;99%
1-chloro-6-methyl-5-nitroisoquinoline
943606-84-6

1-chloro-6-methyl-5-nitroisoquinoline

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

C18H17N3O4

C18H17N3O4

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 20 - 90℃; for 16h; Inert atmosphere;98.4%
acetic anhydride
108-24-7

acetic anhydride

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-(3,5-dimethoxy-phenyl)-acetamide
79257-61-7

N-(3,5-dimethoxy-phenyl)-acetamide

Conditions
ConditionsYield
With pyridine at 0 - 20℃;98%
In toluene at 20℃; for 15h; Time; Inert atmosphere;98%
In toluene at 25℃; for 20h;97%
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

5,5a,10,10a-Tetrahydro-5a,10a-dihydroxy-4-(2-hydroxy-1,3-dioxoindanyl)-1,3-dimethoxyindeno<1,2-b>indol-10-one

5,5a,10,10a-Tetrahydro-5a,10a-dihydroxy-4-(2-hydroxy-1,3-dioxoindanyl)-1,3-dimethoxyindeno<1,2-b>indol-10-one

Conditions
ConditionsYield
In acetic acid for 16h; Ambient temperature;98%
allyl alcohol
107-18-6

allyl alcohol

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-allyl-3,5-dimethoxyaniline

N-allyl-3,5-dimethoxyaniline

Conditions
ConditionsYield
With titanium(IV) isopropylate; MS 4 Angstroem; palladium diacetate; triphenylphosphine In benzene at 80℃; for 3h; Alkylation; N-allylation;98%
para-bromotoluene
106-38-7

para-bromotoluene

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-(4-tolyl)-3,5-dimethoxyaniline
255835-89-3

N-(4-tolyl)-3,5-dimethoxyaniline

Conditions
ConditionsYield
With C60H86O4P2Pd2(2+)*2BF4(1-); sodium t-butanolate In 1,4-dioxane at 80℃; for 1h;98%
With sodium t-butanolate; 1,1'-bis(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)palladium In toluene at 90℃; for 5h;
3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
85657-94-9

N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1h;98%
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;98%
With triethylamine In toluene at 15 - 20℃; for 1.5h; Temperature; Solvent;85.4%
With triethylamine In toluene at 18 - 25℃; for 2h;
With triethylamine In dichloromethane at 20℃; for 2.5h; Cooling with ice;
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

3,5-Dimethoxyaniline
10272-07-8

3,5-Dimethoxyaniline

N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide
85657-94-9

N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 48h; Heating / reflux;98%
With dmap In tetrahydrofuran for 48h; Reflux;98%

3,5-Dimethoxyaniline Chemical Properties

Formula:C8H11NO2
Molecular Weight:153.18
Appearance:Beige crystals
Solubility in water:Soluble
Melting Point:66 – 68
Boiling Point:303
3,5-Dimethoxyaniline`s Synonyms:BENZENAMINE, 3,5-DIMETHOXY-;3,5-DIMETHOXYANILINE;3,5-DIMETHOXYPHENYLAMINE;5-AMINORESORCINOL DIMETHYL ESTER;5-AMINORESORCINOL DIMETHYL ETHER;AKOS 91392;3,5-dimethoxy-benzenamin;3,5-dimethoxy-Benzenamine
Molecular Structure:

3,5-Dimethoxyaniline Toxicity Data With Reference

3,5-Dimethoxyaniline may cause gastrointestinal irritation with nausea, vomiting and diarrhea. respiratory tract irritation and skin or eyes irritation. The toxicological properties of this substance have not been fully investigated

3,5-Dimethoxyaniline Consensus Reports

Stability:Stable under normal temperatures and pressures
First Aid Measures:
Ingestion: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation: Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical ai
Skin: Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Storage:Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling:Wash thoroughly after handling. Use only in a well ventilated area. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.

3,5-Dimethoxyaniline Safety Profile

Hazard Codes: Xn, Xi
Risk Statements: 22-36/37/38-20/21/22
Safety Statements: 26-36-36/37/39-22
WGK Germany: 3
Hazard Note: Irritant
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with skin and if swallowed. 
R 36/37/38 Irritating to eyes, respiratory system and skin. 
Safety Phrases:
S 22 Do not breathe dust. 
S 26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S 36/37/39 Wear suitable protective clothing, gloves and eye/face protection.

3,5-Dimethoxyaniline Specification

Flash Point: 142
Fire Fighting: Wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. To extinguish fire, use water fog, dry chemical, carbon dioxide, or regular foam.
Personal Protection: Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure.
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