| Identification | More | [Name]
2,4-Dichloro-5-methoxyaniline | [CAS]
98446-49-2 | [Synonyms]
2,4-DICHLORO-5-METHOXYANILINE
2,4-Dichloro-5-methoxybenzenamine
5-AMINO-4,6-DICHLOROANISOLE
BENZENAMINE,2,4-DICHLORO-5-METHOXY-
4,6-Dichloro-m-anisidine
2,4-dichloro-5-methoxyphenylamine | [EINECS(EC#)]
619-345-9 | [Molecular Formula]
C7H7Cl2NO | [MDL Number]
MFCD00974410 | [Molecular Weight]
192.04 | [MOL File]
98446-49-2.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN2810 | [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2922290090 |
| Hazard Information | Back Directory | [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 |
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