Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 2h; Reflux; | 100% |
With ammonia; hydrogen In water; isopropyl alcohol at 110℃; under 15001.5 Torr; for 24h; Temperature; Autoclave; | 95% |
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave; | 91% |
Conditions | Yield |
---|---|
With nickel(II) tetrafluoroborate hexahydrate; ammonia; hydrogen; bis(2-diphenylphosphinoethyl)phenylphosphine In 2,2,2-trifluoroethanol at 100℃; for 24h; chemoselective reaction; | 95% |
With ammonia; hydrogen In tert-butyl alcohol at 120℃; for 15h; | 89% |
With ammonium formate In toluene at 80℃; for 3h; Inert atmosphere; chemoselective reaction; | 72% |
piperonylonitrile
A
1,3-benzodioxol-5-ylmethyl amine
B
bis(benzo[d][1,3]dioxol-5-ylmethyl)amine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; nickel dichloride In ethanol at 20℃; for 0.0833333h; | A 85% B 5% |
5-(azidomethyl)benzo[d][1,3]dioxole
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
Stage #1: 5-(azidomethyl)benzo[d][1,3]dioxole With triphenylphosphine at 110℃; for 20h; Staudinger Azide Reduction; Green chemistry; Stage #2: With hydrogenchloride In 1,4-dioxane; diethyl ether Green chemistry; | 85% |
2-Trimethylsilanyl-ethanesulfonic acid (benzo[1,3]dioxol-5-ylmethyl)-amide
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide at 95℃; for 22h; | 80% |
With cesium fluoride In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere; |
methanol
5-(azidomethyl)benzo[d][1,3]dioxole
A
1,3-benzodioxol-5-ylmethyl amine
B
N-methylpiperonylamine
C
1-(N,N-dimethylaminomethyl)-3,4-(methylenedioxy)benzene
Conditions | Yield |
---|---|
With trans-RuCl(phenpyra-Me)(PPh3)2PF6; sodium hydroxide at 125℃; for 3h; Sealed tube; Inert atmosphere; Glovebox; | A 9 %Chromat. B 66% C 7 %Chromat. |
C16H13NO5
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
With ethylenediamine In 1,4-dioxane; propan-1-ol; water for 24h; Reflux; | 20.2% |
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
With hydrogenchloride; steam |
piperonal-(Z)-oxime
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
With sodium amalgam; acetic acid at 50 - 70℃; | |
With sodium amalgam; ethanol; acetic acid | |
With lithium amalgam; diethyl ether |
piperonal-(Z)-oxime
A
1,3-benzodioxol-5-ylmethyl amine
B
bis(benzo[d][1,3]dioxol-5-ylmethyl)amine
Conditions | Yield |
---|---|
With acetic acid; zinc |
piperonal-(Z)-oxime
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
at 50 - 70℃; lower-melting piperonal oxime; |
acetic acid
(E)-3,4-methylenedioxybenzaldehyde oxime
A
1,3-benzodioxol-5-ylmethyl amine
B
bis(benzo[d][1,3]dioxol-5-ylmethyl)amine
piperonal
ethanol
A
1,3-benzodioxol-5-ylmethyl amine
B
bis(benzo[d][1,3]dioxol-5-ylmethyl)amine
piperonal
rac-Ala-OH
A
1,3-benzodioxol-5-ylmethyl amine
B
acetaldehyde
C
methylammonium carbonate
Conditions | Yield |
---|---|
at 160℃; anschliessendes Erwaermen mit wss.-aethanol. Salzsaeure; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dimethylformamide / 130 °C 2: LiAlH4; AlCl3 / diethyl ether / 5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate / 1,4-dioxane; water / 36 h / Reflux 2: ethylenediamine / 1,4-dioxane; propan-1-ol; water / 24 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; | |
With hydrogen; palladium(II) hydroxide In ethanol at 30 - 60℃; for 6h; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: manganese(IV) oxide / dichloromethane 2: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 2 h / 60 °C 3: palladium(II) hydroxide; hydrogen / ethanol / 6 h / 30 - 60 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 5.5 h / -30 - 20 °C / Inert atmosphere 2.1: sodium azide / N,N-dimethyl-formamide / 20 h / 23 °C 3.1: triphenylphosphine / 20 h / 110 °C / Green chemistry 3.2: Green chemistry View Scheme |
1,3-benzodioxol-5-ylmethyl methanesulfonate
1,3-benzodioxol-5-ylmethyl amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium azide / N,N-dimethyl-formamide / 20 h / 23 °C 2.1: triphenylphosphine / 20 h / 110 °C / Green chemistry 2.2: Green chemistry View Scheme |
1,3-benzodioxol-5-ylmethyl amine
acetic anhydride
N-(2H-benzo[3,4-d]-1,3-dioxolen-5-ylmethyl)acetamide
Conditions | Yield |
---|---|
100% |
1,3-benzodioxol-5-ylmethyl amine
fenoxaprop-p-ethyl
B
(R)-2-(4-hydroxyphenoxy)propionic acid ethyl ester
Conditions | Yield |
---|---|
at 20℃; | A 100% B n/a |
1,3-benzodioxol-5-ylmethyl amine
2-(tert-butoxyoxalyl-amino)-5-formyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester
5-(((benzo[1,3]dioxol-5-ylmethyl)-amino)methyl)-2-(tert-butoxyoxalyl-amino)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1h; | 100% |
Stage #1: 1,3-benzodioxol-5-ylmethyl amine; 2-(tert-butoxyoxalyl-amino)-5-formyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1h; Stage #2: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane | 100% |
1,3-benzodioxol-5-ylmethyl amine
3-(N-cyclohexylamino)-4-[N-(4-methylphenyl)amino]-1H-isochromen-1-one
2-{2-[N-(3,4-methylenedioxy)benzyl]carbamoyl}phenyl-2-[N-(4-methyl)phenyl]aminoacetic acid N-cyclohexyl amide
Conditions | Yield |
---|---|
at 20℃; for 24h; Inert atmosphere; | 100% |
pyridine-2-carbaldehyde
1,3-benzodioxol-5-ylmethyl amine
1-(benzo[1,3]dioxol-5-yl)-N-(pyridin-2-yl-methylene)methanamine
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
In water at 20℃; Inert atmosphere; | 90% |
Isopropenyl acetate
1,3-benzodioxol-5-ylmethyl amine
N-(2H-benzo[3,4-d]-1,3-dioxolen-5-ylmethyl)acetamide
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 1.5h; Green chemistry; | 100% |
4-Methoxyphenylacetic acid
1,3-benzodioxol-5-ylmethyl amine
4-oxo-benzaldehyde
tert-butylisonitrile
Conditions | Yield |
---|---|
Stage #1: 1,3-benzodioxol-5-ylmethyl amine; 4-oxo-benzaldehyde In methanol at 60℃; for 0.0833333h; Ugi Condensation; Microwave irradiation; Stage #2: 4-Methoxyphenylacetic acid; tert-butylisonitrile In methanol at 60℃; for 3h; Ugi Condensation; Microwave irradiation; | 100% |
formic acid
1,3-benzodioxol-5-ylmethyl amine
4-oxo-benzaldehyde
tert-butylisonitrile
Conditions | Yield |
---|---|
Stage #1: 1,3-benzodioxol-5-ylmethyl amine; 4-oxo-benzaldehyde In methanol at 60℃; for 0.0833333h; Ugi Condensation; Microwave irradiation; Stage #2: formic acid; tert-butylisonitrile In methanol at 60℃; for 3h; Ugi Condensation; Microwave irradiation; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
at 120℃; |
1,3-benzodioxol-5-ylmethyl amine
benzaldehyde
N-benzylidene piperonylamine
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
In benzene at 65℃; for 0.25h; Microwave irradiation; |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) for 0.05h; | 100% |
Conditions | Yield |
---|---|
With copper(I) chloride; 4 A molecular sieve; oxygen In pyridine at 60℃; for 24h; | 99% |
With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 15h; Reagent/catalyst; | 97% |
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 1500.15 Torr; for 15h; Autoclave; Green chemistry; | 93% |
Conditions | Yield |
---|---|
With azaphosphatrane salt on Merrifield resin In acetonitrile at 20℃; for 12h; Strecker coupling; | 99% |
Conditions | Yield |
---|---|
With azaphosphatrane salt on Merrifield resin In acetonitrile at 20℃; for 8h; Strecker coupling; | 99% |
1,3-benzodioxol-5-ylmethyl amine
acrylic acid methyl ester
methyl 3-piperonylaminopropionate
Conditions | Yield |
---|---|
With azaphosphatrane salt on Merrifield resin In acetonitrile at 20℃; for 24h; Michael addition; | 99% |
With Pseudomonas fluorescence lipase immobilized on hyroxypropyl methyl cellulose support In toluene at 50℃; for 3.5h; Reagent/catalyst; Michael Addition; Enzymatic reaction; chemoselective reaction; |
1,3-benzodioxol-5-ylmethyl amine
1-(1-naphthylmethyl)-4-methoxycarbonylpiperidine
1-(1-naphthylmethyl)-4-[3,4-(methylenedioxy)benzylamino]carbonylpiperidine
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 23℃; Inert atmosphere; | 99% |
1,3-benzodioxol-5-ylmethyl amine
trans-hexahydrobenzoxazol-2-one
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 18h; | 99% |
Conditions | Yield |
---|---|
With Echavarren's catalyst In dichloromethane; water at 50℃; under 1500.15 Torr; for 1h; Inert atmosphere; | 99% |
1,3-benzodioxol-5-ylmethyl amine
carbon monoxide
1,3-bis(benzo[d][1,3]dioxol-5-ylmethyl)urea
Conditions | Yield |
---|---|
With 2C7H9N4*Au(1+)*Cu(1+)*2I(1-) In toluene at 60℃; Autoclave; | 98% |
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating; | 82% |
With C62H52AgAu4N2O4P4(3+)*3F6Sb(1-) In tetrahydrofuran at 60℃; under 3750.38 Torr; for 24h; Inert atmosphere; | 78% |
1,3-benzodioxol-5-ylmethyl amine
5-isocyanato-1,3-benzodioxole
Conditions | Yield |
---|---|
In benzene for 1h; Heating / reflux; | 98% |
1,3-benzodioxol-5-ylmethyl amine
diisopropylamine
N-(benzo[1,3]dioxol-5-ylmethyl)propan-2-amine
Conditions | Yield |
---|---|
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 4h; Reflux; | 98% |
1,3-benzodioxol-5-ylmethyl amine
6-chloro-2-iodo-9-isopropyl-9H-purine
(2-iodo-9-isopropyl-9H-purin-6-yl)(3,4-methylenedioxybenzyl)amine
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; Substitution; | 97% |
Conditions | Yield |
---|---|
Stage #1: N-benzylthiourea With bromomethyl resin In dichloromethane; N,N-dimethyl-formamide at 50℃; for 4h; solid phase reaction; Stage #2: 1,3-benzodioxol-5-ylmethyl amine In dichloromethane; N,N-dimethyl-formamide at 50℃; for 20h; Stage #3: trifluoroacetic acid | 97% |
The 1,3-Benzodioxole-5-methanamine, with the CAS registry number 2620-50-0, is also known as 1-(1,3-Benzodioxol-5-yl)methanamine. It belongs to the product categories of Anilines, Aromatic Amines and Nitro Compounds; Amine. Its EINECS registry number is 220-056-1. This chemical's molecular formula is C8H9NO2 and molecular weight is 151.16. What's more, its IUPAC name is called 1,3-Benzodioxol-5-ylmethanamine. It should be kept in a cold, dry and sealed place.
Physical properties about 1,3-Benzodioxole-5-methanamine are: (1)ACD/LogP: 0.95; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.09; (4)ACD/LogD (pH 7.4): -1.02; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 21.7 Å2; (13)Index of Refraction: 1.592; (14)Molar Refractivity: 40.86 cm3; (15)Molar Volume: 120.5 cm3; (16)Surface Tension: 55 dyne/cm; (17)Density: 1.253 g/cm3; (18)Flash Point: 120.9 °C; (19)Enthalpy of Vaporization: 50.5 kJ/mol; (20)Boiling Point: 267 °C at 760 mmHg; (21)Vapour Pressure: 0.00837 mmHg at 25 °C.
Uses of 1,3-Benzodioxole-5-methanamine: it is used to produce other chemicals. For example, it can react with 1H-Benzo[d][1,3]oxazine-2,4-dione to get 2-Amino-N-benzo[1,3]dioxol-5-ylmethyl-benzamide. The reaction occurs with reagent ethanol and other condition of heating for 2 hours.
When you are dealing with this chemical, you should be very careful. It may destroy living tissue on contact and it may cause burns. This chemical is irritating to eyes, respiratory system and skin. Therefore, you can not breathe the gas/fumes/vapour/spray. You should wear suitable protective clothing. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O1c2ccc(cc2OC1)CN
(2) InChI: InChI=1S/C8H9NO2/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-3H,4-5,9H2
(3) InChIKey: ZILSBZLQGRBMOR-UHFFFAOYSA-N
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