| Identification | Back Directory | [Name]
2-BROMO-4-FLUORO-6-NITROTOLUENE | [CAS]
502496-33-5 | [Synonyms]
2-Bromo-4-fluoro-6-n
Bromo-4-fluoro-6-nit
Bromo-4-fluoro-6-nitrotoluene
2-BROMO-4-FLUORO-6-NITROTOLUENE
3-BroMo-5-fluoro-2-Methylnitrobenzene
1-bromo-5-fluoro-2-methyl-3-nitrobenzene
Benzene, 1-broMo-5-fluoro-2-Methyl-3-nitro-
1-bromo-5-fluoro-2-methyl-3-nitrobenzene,2-Bromo-4-fluoro-6-nitrotoluene
3-Bromo-5-fluoro-2-methylnitrobenzene, 1-Bromo-5-fluoro-2-methyl-3-nitrobenzene | [Molecular Formula]
C7H5BrFNO2 | [MDL Number]
MFCD03094189 | [MOL File]
502496-33-5.mol | [Molecular Weight]
234.02 |
| Chemical Properties | Back Directory | [Boiling point ]
259.4±35.0 °C(Predicted) | [density ]
1.696±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
fused chunks crystalline powder | [color ]
Faint lime fused chunks | [InChI]
InChI=1S/C7H5BrFNO2/c1-4-6(8)2-5(9)3-7(4)10(11)12/h2-3H,1H3 | [InChIKey]
ZVDFTBJXUXQPAU-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC(F)=CC([N+]([O-])=O)=C1C |
| Hazard Information | Back Directory | [Uses]
2-Bromo-4-fluoro-6-nitrotoluene is a pharmaceutical intermediate for the preparation of Remibrutinib. Remibrutinib is used for the treatment of chronic urticaria or urticaria and is currently in clinical development. | [Synthesis]
Step 23a: 3-bromo-5-fluoro-2-methylaniline (Compound 0104-69) was added to a solution of trifluoroacetic acid (40 mL) containing 4-fluoro-2-nitrotoluene (10.0 g, 64.4 mmol). Subsequently, sulfuric acid (12.5 mL) was added slowly and N-bromosuccinimide (NBS, 17.2 g, 96.6 mmol) was added in batches. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was slowly poured into ice water and stirring was continued for 15 min. Extraction was carried out with ethyl acetate, the organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the target product 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (15.0 g, 100% yield) as a yellow oil. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 2.41 (s, 3H), 7.96 (dd, J = 8.0,2.4Hz, 1H), 8.02 (dd, J = 8.0,2.4Hz, 1H). | [References]
[1] Patent: WO2011/130628, 2011, A1. Location in patent: Page/Page column 155
[2] Patent: US2013/102595, 2013, A1. Location in patent: Paragraph 0279; 0280
[3] Patent: JP2015/187145, 2015, A. Location in patent: Paragraph 0252
[4] Patent: WO2007/122410, 2007, A1. Location in patent: Page/Page column 66
[5] Patent: WO2008/152387, 2008, A1. Location in patent: Page/Page column 33 |
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