N-(3,4-methylendioxyphenyl)-N-benzylamine
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h; Catalytic behavior; Reagent/catalyst; | 97% |
5-nitro-1,3-benzodioxole
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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% |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cyclopentadienyl titanium(IV) trichloride; magnesium; triethylamine In tetrahydrofuran at 50℃; for 15h; | 93% |
3,4-(methylenedioxy)-benzeneboronic acid
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h; | 90% |
Methylenedioxybenzene
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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% |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 8h; Green chemistry; | 48% |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran at 20℃; | 40% |
3,4-methylenedioxybenzamide
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With sodium hydroxide; alkaline aqueous sodium hypochlorite solution | |
With alkaline alkali hypobromite solution |
Methylenedioxybenzene
A
benzo[d][1,3]dioxol-4-amine
B
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With potassium hydroxide; diethyl ether |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
3,4-methylenedioxybenzamide
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
beim Erhitzen; |
6-nitrobenzo[d][1,3]dioxole-5-carboxylic acid
A
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With sulfuric acid In methanol; water at 80 - 90℃; Kinetics; Further Variations:; Temperatures; |
piperonylonitrile
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogen peroxide; KOH-solution 2: alkaline alkali hypobromite solution View Scheme |
Piperonylic acid
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous ammonia / 60 - 80 °C / im Rohr 2: alkaline alkali hypobromite solution View Scheme |
acetic anhydride
benzo[1,3]dioxolo-5-ylamine
3,4-methylenedioxyacetanilide
Conditions | Yield |
---|---|
In 1,4-dioxane at 0 - 20℃; for 1h; | 100% |
With triethylamine In dichloromethane at 0℃; for 0.5h; | 97% |
With acetic acid | 95% |
benzo[1,3]dioxolo-5-ylamine
diethyl 2-ethoxymethylenemalonate
diethyl [[3,4-(methylenedioxy)phenylamino]methylene]malonate
Conditions | Yield |
---|---|
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
acetone
N-isopropyl-3,4-(methylenedioxy)aniline
Conditions | Yield |
---|---|
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
6,7-dimethoxy-4-(1-piperazinyl)quinazoline
1,1'-carbonyldiimidazole
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 100% |
benzo[1,3]dioxolo-5-ylamine
p-toluenesulfonyl chloride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 4℃; | 100% |
With pyridine at 0 - 20℃; | 96% |
With silica gel at 20℃; | 92% |
benzaldehyde
benzo[1,3]dioxolo-5-ylamine
N-(3,4-methylendioxyphenyl)-N-benzylamine
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
In 1,4-dioxane Ambient temperature; | 99% |
benzo[1,3]dioxolo-5-ylamine
diisopropylamine
N-isopropyl-3,4-(methylenedioxy)aniline
Conditions | Yield |
---|---|
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
4-methyl-benzaldehyde
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With L-proline In ethanol for 1h; Reflux; Green chemistry; | 99% |
ethanol
benzo[1,3]dioxolo-5-ylamine
N-ethyl-3,4-(methylenedioxy)aniline
Conditions | Yield |
---|---|
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
2-fluoro-4-methylbenzoic Acid
Conditions | Yield |
---|---|
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% |
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
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
3-(2,2,2-trifluoroacetyl)-4H-chromen-4-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 60℃; | 98% |
chloroformic acid ethyl ester
benzo[1,3]dioxolo-5-ylamine
ethyl (1,3-benzodioxolan-5-yl)carbamate
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
N-methyl-3,4-(methylenedioxy)aniline
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
diallyl phosphite
diallyl (benzo[d][1,3]dioxol-5-yl(benzo[d][1,3]dioxol-5-ylamino)methyl)phosphonate
Conditions | Yield |
---|---|
With Amberlite-IR 120 for 0.0166667h; Microwave irradiation; | 98% |
benzo[1,3]dioxolo-5-ylamine
methanesulfonyl chloride
Conditions | Yield |
---|---|
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
tetraacetoxysilane
3,4-methylenedioxyacetanilide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 4h; | 98% |
4-hydroxy-2(5H)-furanone
4-methoxy-benzaldehyde
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
Inert atmosphere; Reflux; | 97% |
methanol
benzo[1,3]dioxolo-5-ylamine
N-methyl-3,4-(methylenedioxy)aniline
Conditions | Yield |
---|---|
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
benzyl alcohol
N-(3,4-methylendioxyphenyl)-N-benzylamine
Conditions | Yield |
---|---|
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
2-Formylphenoxyacetic acid
benzo[1,3]dioxolo-5-ylamine
Conditions | Yield |
---|---|
With ethylenediaminediacetic acid In water for 12h; Reflux; | 96.4% |
tetrahydrofuran-2,4-dione
benzo[1,3]dioxolo-5-ylamine
4-(benzo[d][1,3]dioxol-5-ylamino)furan-2(5H)-one
Conditions | Yield |
---|---|
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
benzo[1,3]dioxolo-5-ylamine
mercaptoacetic acid
C17H13NO5S
Conditions | Yield |
---|---|
In water at 110℃; for 0.15h; Microwave irradiation; chemoselective reaction; | 96% |
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 (CAS NO.14268-66-7) is used as intermediates of drug Ossoli acid, Cinoxacin and Mi Nuosha magnitude.
Hazard CodesXi
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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