| Company Name: |
Energy Chemical |
| Tel: |
400-0056266 |
| Email: |
sales8178@energy-chemical.com |
- Afatinib Impurity
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2025-12-16
- CAS:162012-67-1
- Min. Order: 10mg
- Purity: 99%+ HPLC
- Supply Ability: 1000
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| | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro- Basic information |
| Product Name: | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro- | | Synonyms: | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro-;N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine;4-(3-chloro-4-fiuoro-phen...;4-(3-chloro-4-fiuoro-phenylaMino)-7-fluoro-6-nitroquninazoline;N-(3-chloro-4-fluorophenyl)-N-(7-fluoro-6-nitroquinazolin-4-yl)acetaMide;(3-Chloro-4-fluorophenyl)(7-fluoro-6-nitroquinazolin-4-yl)amine;N-(3-Chloro-4-fluorophenyl)-7-fluoro-6-nitro-4-quinazolinamine;Afatinib intermediate A | | CAS: | 162012-67-1 | | MF: | C14H7ClF2N4O2 | | MW: | 336.68 | | EINECS: | 000-000-0 | | Product Categories: | API intermediates;162012-67-1 | | Mol File: | 162012-67-1.mol |  |
| | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro- Chemical Properties |
| Melting point | 242-244℃ | | Boiling point | 489℃ | | density | 1.616 | | Fp | 249℃ | | storage temp. | 2-8°C(protect from light) | | solubility | DMSO (Slightly), Methanol (Slightly, Sonicated) | | form | Solid | | pka | 5.07±0.70(Predicted) | | color | Yellow to Dark Yellow |
| | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro- Usage And Synthesis |
| Uses | 4-(3-Chloro-4-fluorophenylamino)-7-fluoro-6-nitroquninazoline is an intermediate in the synthesis of Afatinib (A355300), an aminocrotonylamino-substituted quinazoline derivative used for treating cancer and diseases of the respiratory tract, lungs, gastrointestinal tract, bile duct, and gallbladder. | | Synthesis | The general procedure for the synthesis of N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro-4-quinazolinamine from 7-fluoro-6-nitro-4-hydroxyquinazoline and 3-chloro-4-fluoroaniline is as follows:
Method 1 (one-pot reaction):
1. 7-fluoro-6-nitro-4-hydroxyquinazoline (5 g, 23.9 mmol) was added to a 100 mL single neck flask.
2. Phosphoryl chloride (44.6 mL, 478 mmol) was added and heated to reflux at 150 °C for 5 hours.
3. Upon completion of the reaction, phosphorous trichloride was removed by evaporation.
4. The residue was diluted with anhydrous dichloromethane and evaporated again, and the process was repeated 3 times.
5. After dilution with acetonitrile (100 mL), 3-chloro-4-fluoroaniline (2.3 g, 15.8 mmol) was added. 6.
6. Heat to reflux overnight and a yellow solid precipitated during the reaction.
7. The yellow solid was filtered and dried to afford the target product N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro-4-quinazolinamine (4.8 g, 56% yield).
Product characterization data:
1H-NMR (d-DMSO, 400 MHz, δppm): 10.61 (br, 1H), 9.68 (d, J=10.8 Hz, 1H), 8.81 (s, 1H), 8.10-8.13 (d, J=7.6 Hz, 1H), 8.05-8.07 (d, J=8 Hz, 1H), 7.81-7.85 (m. 1H), 7.50-7.54 (d, J=8Hz, 1H). | | References | [1] Patent: EP3181553, 2017, A1. Location in patent: Paragraph 0123; 0124 |
| | 4-Quinazolinamine, N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitro- Preparation Products And Raw materials |
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