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| | 2,4-Dichloro-5-methoxyaniline Basic information |
| Product Name: | 2,4-Dichloro-5-methoxyaniline | | Synonyms: | 2,4-DICHLORO-5-METHOXYANILINE;2,4-Dichloro-5-methoxybenzenamine;4,6-Dichloro-m-anisidine;2,4-dichloro-5-methoxyphenylamine;5-AMINO-4,6-DICHLOROANISOLE;BENZENAMINE,2,4-DICHLORO-5-METHOXY-;5-Amino-2,4-dichloroanisole, 4,5-Dichloro-m-anisidine;5-Amino-2,4-dichloroanisole, 4,6-Dichloro-m-anisidine | | CAS: | 98446-49-2 | | MF: | C7H7Cl2NO | | MW: | 192.04 | | EINECS: | 619-345-9 | | Product Categories: | Heterocyclic Compounds;Anilines, Amides & Amines;Anisoles, Alkyloxy Compounds & Phenylacetates;Chlorine Compounds | | Mol File: | 98446-49-2.mol |  |
| | 2,4-Dichloro-5-methoxyaniline Chemical Properties |
| Melting point | 51 °C | | Boiling point | 290.1±35.0 °C(Predicted) | | density | 1.375±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | pka | 1.59±0.10(Predicted) | | color | Pale Brown | | InChIKey | AJROJTARXSATEB-UHFFFAOYSA-N | | CAS DataBase Reference | 98446-49-2(CAS DataBase Reference) |
| | 2,4-Dichloro-5-methoxyaniline Usage And Synthesis |
| Uses | 2,4-Dichloro-5-methoxyaniline is mainly used to prepare bosutinib intermediate 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-(3-chloropropoxy)-3-quinolinecarbonitrile | | Synthesis | General procedure for the synthesis of 2,4-dichloro-5-methoxyaniline from N-(2,4-dichloro-5-methoxyphenyl)acetamide: N-(2,4-dichloro-5-methoxyphenyl)acetamide (100.7 g, 0.43 mol) was suspended in a mixture of ethanol (500 g), water (500 g), and concentrated hydrochloric acid (300 g, 3 mol), stirred and heated to 70 °C and the reaction lasted for 12 h to obtain a brown solution. After completion of the reaction, ethanol (about 200 g) was evaporated under reduced pressure and the remaining mixture was stirred and cooled to room temperature. After standing for 2 h, the precipitated solid was collected by filtration, washed with water (2 x 200 g) and dried under vacuum at 35 °C to afford 2,4-dichloro-5-methoxyaniline (69.4 g, 84% yield) as a light tan solid with a melting point of 49.5-51.1 °C (literature value 50.5-51.5 °C). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (EI): 1H NMR δ= 3.76 (s, 3H), 5.13 (br s, 2H), 6.58 (s, 1H), 7.23 (s, 1H); mass spectrum (EI) m/z (relative abundance) = 191 (100). | | References | [1] Synthesis (Germany), 2015, vol. 47, # 20, p. 3133 - 3138
[2] Journal of the American Chemical Society, 1919, vol. 41, p. 460 |
| | 2,4-Dichloro-5-methoxyaniline Preparation Products And Raw materials |
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