| Identification | More | [Name]
1-BROMO-2,4-DIFLUORO-5-NITROBENZENE | [CAS]
345-24-4 | [Synonyms]
AURORA KA-7912
BUTTPARK 89\07-60
4-DIFLUORO-5-NITROBENZENE
5-BROMO-2,4-DIFLUORONITROBENZENE
2,4-Difluoro-5-nitrobroMobenzene
2,4-Difluoro-5-BroMonitrobenzene
1-BROMO-2,4-DIFLUORO-5-NITROBENZENE
5-Bromo-2,4-difluoronitrobenzene 98%
Benzene, 1-broMo-2,4-difluoro-5-nitro- | [Molecular Formula]
C6H2BrF2NO2 | [MDL Number]
MFCD00129166 | [Molecular Weight]
237.99 | [MOL File]
345-24-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
19°C(lit.) | [Boiling point ]
85°C 0,4mm | [density ]
1.890±0.06 g/cm3(Predicted) | [refractive index ]
1.5580 to 1.5620 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to lump to clear liquid | [color ]
White or Colorless to Light yellow | [InChI]
InChI=1S/C6H2BrF2NO2/c7-3-1-6(10(11)12)5(9)2-4(3)8/h1-2H | [InChIKey]
OOUUWURPSUSDTD-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC([N+]([O-])=O)=C(F)C=C1F | [CAS DataBase Reference]
345-24-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
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 . | [WGK Germany ]
WGK 3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2904990090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Uses]
1-Bromo-2,4-difluoro-5-nitrobenzene is a nitrobenzene derivative containing fluorine and bromine atom substituents. It can be used as a pharmaceutical intermediate for the preparation of novel N2-phenylpyrimidine-2,4-diamine compounds showing effective inhibition of EGFR mutations, and thus can be effectively used in the treatment of EGFR-mutated cancers. | [Synthesis]
General procedure for the synthesis of 2,4-difluoro-5-bromonitrobenzene from 2,4-difluorobromobenzene: Concentrated HNO3 (34.0 mL) was added slowly and dropwise to a suspension of 1-bromo-2,4-difluorobenzene (53.0 mmol, 6.00 mL) in concentrated H2SO4 (38.5 mL) at 0 °C, ensuring that the internal temperature was maintained below 0 °C. The reaction mixture was stirred for 10 minutes with vigorous stirring. The reaction mixture was continued to be stirred at 0 °C for 10 min and subsequently poured into an ice/water mixture under vigorous stirring. The mixture was extracted with ether (ET20, 3 x 100 mL). The combined organic phases were washed sequentially with aqueous NaHCO3 (3 x 100 mL) and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by fast chromatography (eluent: EtOAc/hexane=1:9) to afford 5-bromo-2,4-difluoronitrobenzene as a yellow oil (12.2 g, 97% yield).1H NMR (400 MHz, CDCl3) δ 8.45 (t, 1H, J=7.5 Hz), 7.16 (dd, 1H, J=11.0,8.6 Hz) ; ESMS m/z: 240, 238, 223, 221, 112. | [References]
[1] Synthesis, 1998, # 8, p. 1101 - 1103
[2] Patent: WO2004/5257, 2004, A1. Location in patent: Page 67
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3870 - 3882
[4] Patent: US2005/154020, 2005, A1. Location in patent: Page/Page column 8
[5] Patent: US2005/154022, 2005, A1. Location in patent: Page/Page column 9 |
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