Product Name

  • Name

    3,4-(Methylenedioxy)aniline

  • EINECS 238-161-6
  • CAS No. 14268-66-7
  • Article Data49
  • CAS DataBase
  • Density 1.332 g/cm3
  • Solubility slightly soluble in water
  • Melting Point 39-41 °C(lit.)
  • Formula C7H7NO2
  • Boiling Point 267.9 °C at 760 mmHg
  • Molecular Weight 137.138
  • Flash Point 142.8 °C
  • Transport Information
  • Appearance dark brown to black low melting solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 14268-66-7 (3,4-(Methylenedioxy)aniline)
  • Hazard Symbols IrritantXi
  • Synonyms Aniline,3,4-(methylenedioxy)- (6CI,8CI);(Benzo[1,3]dioxol-5-yl)amine;(Benzodioxol-5-yl)amine;1,2-(Methylenedioxy)-4-aminobenzene;1,3-Benzodioxolan-6-amine;1-Amino-3,4-(methylenedioxy)benzene;3,4-(Methylenedioxy)-1-aminobenzene;1,3-Benzodioxol-5-amine;3,4-Methylendioxyaniline;3,4-Methylenedioxybenzeneamine;4-Amino-1,2-(methylenedioxy)benzene;5-Amino-1,3-benzodioxole;Benzo[d][1,3]dioxol-5-amine;Benzodioxol-5-amine;NSC155176;
  • PSA 44.48000
  • LogP 1.57870

Synthetic route

N-(3,4-methylendioxyphenyl)-N-benzylamine
32932-20-0

N-(3,4-methylendioxyphenyl)-N-benzylamine

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h; Catalytic behavior; Reagent/catalyst;97%
5-nitro-1,3-benzodioxole
2620-44-2

5-nitro-1,3-benzodioxole

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With C30H29BrMnNO2P2; hydrogen; potassium carbonate In toluene at 130℃; under 60006 Torr; for 24h; Glovebox; Autoclave; chemoselective reaction;96%
With hydrogen; nickel In ethanol at 60℃; under 18751.9 Torr; for 2h; Solvent; Pressure; Concentration;95.9%
With C36H56Cl3CrN2O; magnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;85%
1,2-(methylenedioxy)-4-bromobenzene
2635-13-4

1,2-(methylenedioxy)-4-bromobenzene

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; C17H14N2O3; potassium hydroxide In ethanol at 60℃; for 24h; Schlenk technique; Inert atmosphere;95%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 18h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere;90%
With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide In water at 100℃; for 12h;73%
With ammonium hydroxide; diethylenetriaminopentaacetic acid; copper(II) oxide; potassium hydroxide In water at 100℃; for 12h; Sealed tube;73%
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene 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;
66%
5-iodo-1,3-benzodioxole
5876-51-7

5-iodo-1,3-benzodioxole

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; N1-(furan-2-ylmethyl)-N2-(2-methylnaphthalen-1-yl)oxalamide; potassium hydroxide In ethanol at 80℃; for 24h; Schlenk technique; Inert atmosphere;95%
C11H9NO4

C11H9NO4

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With chloro-trimethyl-silane; cyclopentadienyl titanium(IV) trichloride; magnesium; triethylamine In tetrahydrofuran at 50℃; for 15h;93%
3,4-(methylenedioxy)-benzeneboronic acid
94839-07-3

3,4-(methylenedioxy)-benzeneboronic acid

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;90%
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h;60%
Stage #1: Methylenedioxybenzene With sulfuric acid; hydroxylamine hydrochloride In acetonitrile at 25℃; for 0.166667h;
Stage #2: With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 25℃; Inert atmosphere; Sealed tube;
57%
1-(benzo[d][1,3]dioxole-5-carbonyl)piperidine-2,6-dione

1-(benzo[d][1,3]dioxole-5-carbonyl)piperidine-2,6-dione

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
Stage #1: 1-(benzo[d][1,3]dioxole-5-carbonyl)piperidine-2,6-dione With Benzophenone imine; 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; Ni(1,5-cyclooctadiene)2; lithium chloride In toluene at 170℃; Glovebox; Inert atmosphere; Sealed tube;
Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃;
55%
2-(benzo[d][1,3]dioxol-5-yloxy)propanamide
1181403-64-4

2-(benzo[d][1,3]dioxol-5-yloxy)propanamide

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 8h; Green chemistry;48%
C20H15NO2

C20H15NO2

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃;40%
3,4-methylenedioxybenzamide
4847-94-3

3,4-methylenedioxybenzamide

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With sodium hydroxide; alkaline aqueous sodium hypochlorite solution
With alkaline alkali hypobromite solution
Methylenedioxybenzene
274-09-9

Methylenedioxybenzene

A

benzo[d][1,3]dioxol-4-amine
1668-84-4

benzo[d][1,3]dioxol-4-amine

B

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With sulfuric acid; hydroxylamine-O-sulfonic acid; iron(II) sulfate In water; N,N-dimethyl-formamide at 30 - 35℃; for 1h; Yield given. Yields of byproduct given;
2,4-dinitroso-2,4-diaza-glutaric acid diethyl ester
857829-30-2

2,4-dinitroso-2,4-diaza-glutaric acid diethyl ester

4-amino-1.2-dioxy-benzene hydrochloride

4-amino-1.2-dioxy-benzene hydrochloride

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; diethyl ether
4-nitro-pyrocatechol-methylene ether

4-nitro-pyrocatechol-methylene ether

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With hydrogenchloride; tin
3,4-methylenedioxybenzamide
4847-94-3

3,4-methylenedioxybenzamide

potassium hypobromite

potassium hypobromite

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
beim Erhitzen;
6-nitrobenzo[d][1,3]dioxole-5-carboxylic acid
716-32-5

6-nitrobenzo[d][1,3]dioxole-5-carboxylic acid

A

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

B

6-amino-piperonylic acid

6-amino-piperonylic acid

Conditions
ConditionsYield
With hydrogenchloride; tin
2-benzo[1,3]dioxol-5-yl-1,1,1,3,3,3-hexamethyl-disilazane

2-benzo[1,3]dioxol-5-yl-1,1,1,3,3,3-hexamethyl-disilazane

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether
1-(benzo[d][1,3]dioxol-5-yl)urea

1-(benzo[d][1,3]dioxol-5-yl)urea

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
With sulfuric acid In methanol; water at 80 - 90℃; Kinetics; Further Variations:; Temperatures;
piperonylonitrile
4421-09-4

piperonylonitrile

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen peroxide; KOH-solution
2: alkaline alkali hypobromite solution
View Scheme
Piperonylic acid
94-53-1

Piperonylic acid

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen chloride
2: aqueous ammonia / 60 - 80 °C / im Rohr
3: alkaline alkali hypobromite solution
View Scheme
Multi-step reaction with 3 steps
1.1: thionyl chloride / 2 h / Reflux
2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C
3.1: Ni(1,5-cyclooctadiene)2; Benzophenone imine; 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; lithium chloride / toluene / 170 °C / Glovebox; Inert atmosphere; Sealed tube
3.2: 20 °C
View Scheme
methyl 3,4-methylenedioxybenzoate
326-56-7

methyl 3,4-methylenedioxybenzoate

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous ammonia / 60 - 80 °C / im Rohr
2: alkaline alkali hypobromite solution
View Scheme
acetic anhydride
108-24-7

acetic anhydride

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

3,4-methylenedioxyacetanilide
13067-19-1

3,4-methylenedioxyacetanilide

Conditions
ConditionsYield
In 1,4-dioxane at 0 - 20℃; for 1h;100%
With triethylamine In dichloromethane at 0℃; for 0.5h;97%
With acetic acid95%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

diethyl 2-ethoxymethylenemalonate
87-13-8

diethyl 2-ethoxymethylenemalonate

diethyl [[3,4-(methylenedioxy)phenylamino]methylene]malonate
17394-77-3

diethyl [[3,4-(methylenedioxy)phenylamino]methylene]malonate

Conditions
ConditionsYield
In ethanol at 90℃; for 18h;100%
In benzene for 3.5h; Reflux;96%
In benzene for 3.5h; Heating;71%
In benzene for 3h; Reflux;
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

acetone
67-64-1

acetone

N-isopropyl-3,4-(methylenedioxy)aniline
10368-14-6

N-isopropyl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 17h;100%
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran for 15h; Ambient temperature;
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

6,7-dimethoxy-4-(1-piperazinyl)quinazoline
21584-72-5

6,7-dimethoxy-4-(1-piperazinyl)quinazoline

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid benzo[1,3]dioxol-5-ylamide

4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid benzo[1,3]dioxol-5-ylamide

Conditions
ConditionsYield
Stage #1: benzo[1,3]dioxolo-5-ylamine; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 4h;
Stage #2: 6,7-dimethoxy-4-(1-piperazinyl)quinazoline In dichloromethane at 20℃; Further stages.;
100%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

ethyl 2-(benzo[1,3]dioxol-5-ylimino)acetate

ethyl 2-(benzo[1,3]dioxol-5-ylimino)acetate

Conditions
ConditionsYield
With magnesium sulfate In toluene at 25℃; for 0.5h;100%
In toluene at 23℃; for 1h; Molecular sieve; Inert atmosphere;
In dichloromethane for 0.333333h; Inert atmosphere;
benzaldehyde
100-52-7

benzaldehyde

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

C14H11NO2
32932-19-7

C14H11NO2

Conditions
ConditionsYield
In ethanol for 1h; Sonication;100%
In ethanol for 5h; Reflux;
In toluene for 6h; Reflux;
In neat (no solvent) at 20℃; for 0.5h; Schlenk technique; Molecular sieve; Inert atmosphere;
1,4-oxathiane-2,6-dione
3261-87-8

1,4-oxathiane-2,6-dione

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

C11H11NO5S

C11H11NO5S

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(benzo[d][1,3]dioxol-5-yl)-4-methylbenzenesulfonamide

N-(benzo[d][1,3]dioxol-5-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With pyridine at 0 - 20℃;96%
With silica gel at 20℃;92%
benzaldehyde
100-52-7

benzaldehyde

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

N-(3,4-methylendioxyphenyl)-N-benzylamine
32932-20-0

N-(3,4-methylendioxyphenyl)-N-benzylamine

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 17h;100%
With tetra(n-butyl)ammonium hydrogensulfate; dimethyl sulfoxide at 20℃; for 5h; Electrolysis;30%
With sodium triacetoxy borohydride; acetic acid In dichloromethane at 0 - 20℃;
Multi-step reaction with 2 steps
1: neat (no solvent) / 0.5 h / 20 °C / Schlenk technique; Molecular sieve; Inert atmosphere
2: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / neat (no solvent) / 24 h / 20 °C / Schlenk technique; Inert atmosphere
View Scheme
1,3-cyclopentadione
3859-41-4

1,3-cyclopentadione

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

3-(Benzo[1,3]dioxol-5-ylamino)-cyclopent-2-enone

3-(Benzo[1,3]dioxol-5-ylamino)-cyclopent-2-enone

Conditions
ConditionsYield
In 1,4-dioxane Ambient temperature;99%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

diisopropylamine
108-18-9

diisopropylamine

N-isopropyl-3,4-(methylenedioxy)aniline
10368-14-6

N-isopropyl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Inert atmosphere;99%
2-Hydroxy-1,4-naphthoquinone
83-72-7

2-Hydroxy-1,4-naphthoquinone

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

12-(4-methylphenyl)-5,10-dihydro-benzo[i][1,3]dioxolo[4,5-b]acridine-6,11-dione

12-(4-methylphenyl)-5,10-dihydro-benzo[i][1,3]dioxolo[4,5-b]acridine-6,11-dione

Conditions
ConditionsYield
With L-proline In ethanol for 1h; Reflux; Green chemistry;99%
ethanol
64-17-5

ethanol

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

N-ethyl-3,4-(methylenedioxy)aniline
32953-14-3

N-ethyl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
With cesiumhydroxide monohydrate; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3 at 110℃; Schlenk technique; Inert atmosphere;99%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

2-fluoro-4-methylbenzoic Acid
7697-23-6

2-fluoro-4-methylbenzoic Acid

N-(benzo[d][1,3]dioxol-5-yl)-2-fluoro-4-methylbenzamide

N-(benzo[d][1,3]dioxol-5-yl)-2-fluoro-4-methylbenzamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;99%
5-methylene-4-phenyl-4-vinyl-1,3-dioxolan-2-one

5-methylene-4-phenyl-4-vinyl-1,3-dioxolan-2-one

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

1-(benzo[d][1,3]dioxol-5-yl)-2-methyl-3-phenyl-1H-pyrrole

1-(benzo[d][1,3]dioxol-5-yl)-2-methyl-3-phenyl-1H-pyrrole

Conditions
ConditionsYield
With palladium(II) trifluoroacetate; trifuran-2-yl-phosphane In dichloromethane at 20℃; for 12h;99%
[5-(3-methoxybenzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]acetic acid
1184304-26-4

[5-(3-methoxybenzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]acetic acid

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

N-(benzo[1,3]dioxol-5-yl)-2-[5-(3-methoxybenzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetamide
1184304-64-0

N-(benzo[1,3]dioxol-5-yl)-2-[5-(3-methoxybenzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetamide

Conditions
ConditionsYield
Stage #1: [5-(3-methoxybenzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]acetic acid With triethylamine In tetrahydrofuran at -5 - 0℃;
Stage #2: With chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 1h;
Stage #3: benzo[1,3]dioxolo-5-ylamine In tetrahydrofuran at 20℃; for 12h;
98%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

3-(2,2,2-trifluoroacetyl)-4H-chromen-4-one
160856-31-5

3-(2,2,2-trifluoroacetyl)-4H-chromen-4-one

3-{[(1,3-benzodioxol-5-yl)amino]methylene}-2-hydroxy-2-(trifluoromethyl)chroman-4-one

3-{[(1,3-benzodioxol-5-yl)amino]methylene}-2-hydroxy-2-(trifluoromethyl)chroman-4-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 60℃;98%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

ethyl (1,3-benzodioxolan-5-yl)carbamate
165330-00-7

ethyl (1,3-benzodioxolan-5-yl)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;98%
With triethylamine In tetrahydrofuran at 20℃; for 4h;85%
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;
With triethylamine In tetrahydrofuran at 20℃; for 0.5h;
formaldehyd
50-00-0

formaldehyd

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

N-methyl-3,4-(methylenedioxy)aniline
34060-22-5

N-methyl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
Stage #1: formaldehyd; benzo[1,3]dioxolo-5-ylamine With sodium methylate In methanol at 20℃; for 24h;
Stage #2: With methanol; sodium tetrahydroborate at 40℃; for 3h;
98%
Stage #1: formaldehyd; benzo[1,3]dioxolo-5-ylamine With sodium methylate In methanol at 20℃; for 18h;
Stage #2: With sodium tetrahydroborate In methanol at 40℃; for 3h;
1.43 g
piperonal
120-57-0

piperonal

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

diallyl phosphite
23679-20-1

diallyl phosphite

diallyl (benzo[d][1,3]dioxol-5-yl(benzo[d][1,3]dioxol-5-ylamino)methyl)phosphonate
1449479-35-9

diallyl (benzo[d][1,3]dioxol-5-yl(benzo[d][1,3]dioxol-5-ylamino)methyl)phosphonate

Conditions
ConditionsYield
With Amberlite-IR 120 for 0.0166667h; Microwave irradiation;98%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(benzo[d][1,3]dioxol-5-yl)methanesulfonamide

N-(benzo[d][1,3]dioxol-5-yl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 12h;98%
With silica gel at 20℃;95%
Stage #1: benzo[1,3]dioxolo-5-ylamine With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 24h;
89.2%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

tetraacetoxysilane
562-90-3

tetraacetoxysilane

3,4-methylenedioxyacetanilide
13067-19-1

3,4-methylenedioxyacetanilide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 4h;98%
4-hydroxy-2(5H)-furanone
541-57-1

4-hydroxy-2(5H)-furanone

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

9-(4-methoxyphenyl)-6,9-dihydro-[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one

9-(4-methoxyphenyl)-6,9-dihydro-[1,3]dioxolo[4,5-g]furo[3,4-b]quinolin-8(5H)-one

Conditions
ConditionsYield
Inert atmosphere; Reflux;97%
methanol
67-56-1

methanol

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

N-methyl-3,4-(methylenedioxy)aniline
34060-22-5

N-methyl-3,4-(methylenedioxy)aniline

Conditions
ConditionsYield
With cesiumhydroxide monohydrate; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3 at 110℃; Schlenk technique; Inert atmosphere;97%
With dimanganese decacarbonyl; potassium tert-butylate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;92%
With potassium tert-butylate; C38H37ClN2PRu(1+)*C32H12BF24(1-) In neat (no solvent) at 110℃; for 12h; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry;92%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

benzyl alcohol
100-51-6

benzyl alcohol

N-(3,4-methylendioxyphenyl)-N-benzylamine
32932-20-0

N-(3,4-methylendioxyphenyl)-N-benzylamine

Conditions
ConditionsYield
With C50H38ClN3O2P2RuS; potassium hydroxide In toluene at 100℃; for 12h;97%
With iron(III) oxide; potassium hydroxide In toluene at 135℃; for 24h; Inert atmosphere; Sealed tube;80%
With zinc(II) nitrate hexahydrate; potassium tert-butylate In toluene at 140℃; for 36h; Sealed tube; Inert atmosphere; Schlenk technique;72%
isatoic anhydride
118-48-9

isatoic anhydride

2-Formylphenoxyacetic acid
6280-80-4

2-Formylphenoxyacetic acid

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

2-(phenoxyacetic acid-2-yl)-3-(benzo[d]-[1,3]dioxol-5-yl)-2,3-dihydroquinazolin-4(1H)-one

2-(phenoxyacetic acid-2-yl)-3-(benzo[d]-[1,3]dioxol-5-yl)-2,3-dihydroquinazolin-4(1H)-one

Conditions
ConditionsYield
With ethylenediaminediacetic acid In water for 12h; Reflux;96.4%
tetrahydrofuran-2,4-dione
4971-56-6

tetrahydrofuran-2,4-dione

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

4-(benzo[d][1,3]dioxol-5-ylamino)furan-2(5H)-one
200053-21-0

4-(benzo[d][1,3]dioxol-5-ylamino)furan-2(5H)-one

Conditions
ConditionsYield
In acetonitrile for 0.666667h; Microwave irradiation; Reflux;96%
In 1,4-dioxane Product distribution; Ambient temperature; var. anilines;
In 1,4-dioxane Ambient temperature;
piperonal
120-57-0

piperonal

benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

mercaptoacetic acid
68-11-1

mercaptoacetic acid

C17H13NO5S
1129572-76-4

C17H13NO5S

Conditions
ConditionsYield
In water at 110℃; for 0.15h; Microwave irradiation; chemoselective reaction;96%

3,4-(Methylenedioxy)aniline Chemical Properties

IUPAC Name: 1,3-Benzodioxol-5-amine
Synonyms: 1,3-benzodioxol-5-amine ; 1-Amino-3,4-methylenedioxybenzene ; 4-Amino-1,2-methylenedioxybenzene ; Aniline, 3,4-(methylenedioxy)- 
Product Categories: Anilines, Aromatic Amines and Nitro Compounds
Molecular Structure of 3,4-(Methylenedioxy)aniline (CAS NO.14268-66-7) :
Molecular Formula of 3,4-(Methylenedioxy)aniline (CAS NO.14268-66-7) : C7H7NO2
Molecular Weight of 3,4-(Methylenedioxy)aniline (CAS NO.14268-66-7) : 137.14
CAS NO: 14268-66-7
EINECS : 238-161-6
Mol File: 14268-66-7.mol
BRN : 4919
Index of Refraction: 1.63
Surface Tension: 61.7 dyne/cm
Density: 1.332 g/cm3
Flash Point: 142.8 °C
Enthalpy of Vaporization: 50.59 kJ/mol
Boiling Point: 267.9 °C at 760 mmHg
Vapour Pressure: 0.00795 mmHg at 25°C
Melting point: 39-41 °C(lit.)
Water Solubility : slightly soluble
Sensitive : Air & Light Sensitive
Appearance:dark brown to black low melting solid
 

3,4-(Methylenedioxy)aniline Uses

 3,4-(Methylenedioxy)aniline (CAS NO.14268-66-7) is used as intermediates of drug Ossoli acid, Cinoxacin and Mi Nuosha magnitude.

3,4-(Methylenedioxy)aniline Safety Profile

Hazard CodesIrritantXi
Risk Statements 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany 3
Hazard Note Irritant
HS Code 29329970

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