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| | 3,4-(Methylenedioxy)aniline Basic information |
| Product Name: | 3,4-(Methylenedioxy)aniline | | Synonyms: | 5-Amino-1,3-benzodioxole 98%;1,3-Benzodioxol-5-amine, 3,4-(Methylenedioxy)aniline;5-Amino-1,3-benzodioxole
4-Amino-1,2-methylenedioxybenzene;3,4-METHYLENEDIOXYANILINE (STABILISED WI;3,4-(Methylenedioxy)aniline, 97% 10GR;3,4-(Methylenedioxy)aniline, 97% 50GR;4-aMino-1,3-benzodioxole;3,4-(Methylenedioxy)aniline, 98+%, 98+% | | CAS: | 14268-66-7 | | MF: | C7H7NO2 | | MW: | 137.14 | | EINECS: | 238-161-6 | | Product Categories: | Anilines, Aromatic Amines and Nitro Compounds | | Mol File: | 14268-66-7.mol |  |
| | 3,4-(Methylenedioxy)aniline Chemical Properties |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | Hazard Note | Irritant | | TSCA | Yes | | HazardClass | 6.1 | | HS Code | 29329970 |
| | 3,4-(Methylenedioxy)aniline Usage And Synthesis |
| 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. | | 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.] |
| | 3,4-(Methylenedioxy)aniline Preparation Products And Raw materials |
| 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) |
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