| Identification | More | [Name]
2-Bromo-3-fluoroaniline | [CAS]
111721-75-6 | [Synonyms]
2-BROMO-3-FLUOROANILINE
2-BROMO-3-FLUORO-PHENYLAMINE | [Molecular Formula]
C6H5BrFN | [MDL Number]
MFCD07369915 | [Molecular Weight]
190.01 | [MOL File]
111721-75-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
32-34 °C | [Boiling point ]
229.8±20.0 °C(Predicted) | [density ]
1.670 | [Fp ]
94°(201°F) | [refractive index ]
1.5830 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline | [pka]
1.52±0.10(Predicted) | [color ]
Off-white | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C6H5BrFN/c7-6-4(8)2-1-3-5(6)9/h1-3H,9H2 | [InChIKey]
XZRSXRUYZXBTGD-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=CC(F)=C1Br | [CAS DataBase Reference]
111721-75-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow liquid | [Uses]
2-Bromo-3-fluoroaniline is used as pharmaceutical intermediate. | [Synthesis Reference(s)]
Journal of Heterocyclic Chemistry, 27, p. 2151, 1990 DOI: 10.1002/jhet.5570270755 | [Synthesis]
General procedure for the synthesis of 2-bromo-3-fluoroaniline from 2-bromo-3-fluoro nitrobenzene: 2-bromo-1-fluoro-3-nitrobenzene (1.0 g, 5.0 mmol) was dissolved in methanol (50 mL) at 0 °C, and NiCl? (2.2 g, 10 mmol) and NaBH? (0.50 g, 14 mmol) were added sequentially. After the addition was completed, the reaction mixture was stirred at 0 °C for 5 min. Subsequently, the reaction was quenched by the addition of water (20 mL) and extracted with ethyl acetate (20 mL x 3). The organic layers were combined, dried over anhydrous Na?SO? and concentrated under reduced pressure to afford 2-bromo-3-fluoroaniline (600 mg, 70% yield). The product was characterized by 1H NMR (400 MHz, CDCl?): δ 7.07-7.02 (m, 1H), 6.55-6.49 (m, 1H), 4.22 (br s, 2H). | [References]
[1] Patent: CN108002976, 2018, A. Location in patent: Paragraph 0045; 0047; 0050; 0051; 0060; 0069
[2] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3416 - 3437
[3] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 121
[4] Patent: US2011/98311, 2011, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1674 |
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