- 4-Chloro-3-fluoroaniline
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- $5.00 / 1KG
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2025-09-25
- CAS:367-22-6
- Min. Order: 1KG
- Purity: 98%
- Supply Ability: g-kg-tons, free sample is available
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| | 4-Chloro-3-fluoroaniline Basic information | | Uses |
| | 4-Chloro-3-fluoroaniline Chemical Properties |
| Melting point | 61 | | Boiling point | 226°C(lit.) | | density | 1.349±0.06 g/cm3(Predicted) | | Fp | 60 - 62°C | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | soluble in Methanol | | form | powder to crystal | | pka | 2.94±0.10(Predicted) | | color | White to Gray to Red | | BRN | 2716278 | | InChI | InChI=1S/C6H5ClFN/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2 | | InChIKey | ACMJJQYSPUPMPN-UHFFFAOYSA-N | | SMILES | C1(N)=CC=C(Cl)C(F)=C1 | | CAS DataBase Reference | 367-22-6(CAS DataBase Reference) |
| Hazard Codes | T,Xi | | Risk Statements | 20/21/22-36/37/38 | | Safety Statements | 26-36/37/39-63-45-38 | | RIDADR | UN2811 | | WGK Germany | 3 | | Hazard Note | Toxic | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29214200 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 4-Chloro-3-fluoroaniline Usage And Synthesis |
| Uses | 4-Chloro-3-fluoroaniline is used in the synthesis of Methyl 5-Chloro-4-fluoro-1H-indole-2-carboxylate; a key intermediate towards phosphoindole inhibitors of HIV non-nucleoside reverse transcriptase. 4-Chloro-3-fluoroaniline is also used in the synthesis of 3-Deschloro-4-desfluoro-4-chloro-3-fluoro Gefitinib (D289540) which is an impurity of the tyrosine kinase inhibitor Gefitinib. | | Chemical Properties | White to light yellow solid | | Uses | 4-Chloro-3-fluoroaniline is used in the synthesis of Methyl 5-Chloro-4-fluoro-1H-indole-2-carboxylate | | Synthesis | 1. A CHCl3 (20.0 mL) solution of N-chlorosuccinimide (NCS) was added slowly and dropwise to a stirred CHCl3 (30.0 mL) solution of 3-fluoroaniline (1.11 g, 10.0 mmol) at 0 °C.
2. The reaction mixture was stirred continuously at 0 °C for 42 hours.
3. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in Et2O.
4. The mixture was washed with water and subsequently dried with MgSO4.
5. After concentration under reduced pressure, the mixture was purified by rapid chromatography on silica gel, using EtOAc/hexane as eluent, to afford 4-chloro-3-fluoroaniline (259.4 g, 18% yield) as a crystalline solid.
6. To a stirred solution of the above 4-chloro-3-fluoroaniline (259.4 mg, 1.78 mmol) in THF (8.9 mL) was added ethyl chloroacetate (237.3 μL, 2.14 mmol) and Et3N (296.6 μL, 2.14 mmol) sequentially at 0 °C.
7. The mixture was stirred at room temperature for 12 hours.
8. After filtration to remove the precipitate, the filtrate was concentrated under reduced pressure.
9. The residue was dissolved in EtOAc, washed sequentially with 1.0 M HCl, saturated NaHCO3 solution and brine, and then dried with MgSO4.
10. After concentration under pressure, 3-fluoro-4-chloroaniline 6a (435.2 mg, 99% yield) was obtained as brown crystals, which could be used without further purification. | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 11, p. 3282 - 3285
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 9, p. 2518 - 2526
[3] Patent: EP1342717, 2003, A1
[4] Patent: US2003/236267, 2003, A1. Location in patent: Page 30 |
| | 4-Chloro-3-fluoroaniline Preparation Products And Raw materials |
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