| Identification | More | [Name]
3,4-(Methylenedioxy)aniline | [CAS]
14268-66-7 | [Synonyms]
1,3-BENZODIOXOL-5-AMINE
3,4-(METHYLENEDIOXY)ANILINE
4-AMINO-1,2-METHYLENEDIOXYBENZENE
5-AMINO-1,3-BENZODIOXOLE
AKOS BBS-00004239
(BENZO[1,3]DIOXOL-5-YL)AMINE
1-Amino-3,4-dimethylenedioxybenzene
1-Amino-3,4-methylenedioxybenzene
5-Aminobenzodioxole
Aniline, 3,4-(methylenedioxy)-
Methylenedioxyaniline
3,4-(Methylenedioxy)aniline, 98+%
(BENZO[1,3]DIOXOL-5-YL)AMIN
3,4-Methylenedioxyaniline 98%
3,4-methylendioxy-analin | [EINECS(EC#)]
238-161-6 | [Molecular Formula]
C7H7NO2 | [MDL Number]
MFCD00005832 | [Molecular Weight]
137.14 | [MOL File]
14268-66-7.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
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 | [TSCA ]
Yes | [HazardClass ]
6.1 | [HS Code ]
29329970 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
3,4-METHYLENEDIOXYPHENYLBORONIC ACID-->1,2-(Methylenedioxy)-4-nitrobenzene-->3,4-Methylenedioxyacetophenone-->4-Bromo-1,2-(methylenedioxy)benzene-->5-CHLORO-1,3-BENZODIOXOLE-->Sesamol-->1-IODO-3,4-METHYLENEDIOXYBENZENE-->1,3-Benzodioxole | [Preparation Products]
3,4-(METHYLENEDIOXY)PHENYL ISOCYANATE-->5,6-METHYLENEDIOXYINDOLE-->N-Ethyl-3,4-(methylenedioxy)aniline-->4-(BENZO[1,3]DIOXOL-5-YLCARBAMOYL)-BUTYRIC ACID-->Benzamide, 2-amino-N-1,3-benzodioxol-5-yl- (9CI)-->1-(1,3-BENZODIOXOL-5-YL)PIPERIDIN-4-ONE-->ASISCHEM N35536-->Carbamic acid, 1,3-benzodioxol-5-yl-, 1,1-dimethylethyl ester (9CI) |
| Hazard Information | Back Directory | [Chemical Properties]
dark brown to black low melting solid | [Uses]
3,4-(Methylenedioxy)aniline is an pharmaceutically important aniline derivative. It undergoes N-alkylation with cyclic secondary alkylamines in the presence of Shvo catalyst to yield N-arylpyrrolidines. 3,4-(Methylenedioxy)aniline was used in the synthesis of γ-glutamylanilides. | [General Description]
3,4-(Methylenedioxy)aniline is an pharmaceutically important aniline derivative. It undergoes N-alkylation with cyclic secondary alkylamines in the presence of Shvo catalyst to yield N-arylpyrrolidines. | [Synthesis]
A 10mL-sealed tube was charged with 5-bromobenzo[d][1,3]dioxole (1mmol), CuI (19mg, 0.1mmol), and DMEDA (13mg/16μL, 0.15mmol) in NH4OH (1.5mL, 27% NH3 in H2O) and DMSO (0.5mL). The tube was flushed with Ar gas before being capped. The solution was stirred at 130°C or 110°C for the given times. The resulting suspension was cooled to room temperature, and saturated aqueous Na2SO4 solution (5mL) was added. The resulting solution was extracted with EtOAc (20mL×3). The organic layer was separated, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography to give 3,4-(Methylenedioxy)aniline.
| [Purification Methods]
Crystallise the base from pet ether and/or distil it in a vacuum. The hydrochloride has m 198o(dec). [Sonn & Benirschke Chem Ber 54 1734 1921, Beilstein 19 H 328, 19 II 341, 19 III/IV 4056.] |
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