| Identification | Back Directory | [Name]
3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene | [CAS]
443882-99-3 | [Synonyms]
oro-1-(3-fL
oxy)-4-nitrobenzene
2-Chloro-1-((3-fluorobenzyl)
Lapatinib genotoxic impurity 2
2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-
4-(3-Fluorobenzyloxy)-3-chloronitrobenzene
3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene
1-(3-fluorobenzyloxy)-2-chloro-4-nitrobenzene
2-Chloro-1-(3-fluoro-benzyloxy)-4-nitrobenzene
3-Chloro-4-(3-fluorobenzyloxy)nitrobenzene >
2-chloro-1-[(3-fluorophenyl)methoxy]-4-nitrobenzene
1-Fluoro-3-[(4-nitro-2-chlorophenoxy)Methyl]benzene
Benzene,2-chloro-1-[(3-fluorophenyl)Methoxy]-4-nitro- | [Molecular Formula]
C13H9ClFNO3 | [MDL Number]
MFCD06809827 | [MOL File]
443882-99-3.mol | [Molecular Weight]
281.67 |
| Chemical Properties | Back Directory | [Melting point ]
99.0 to 103.0 °C | [Boiling point ]
400.5±35.0 °C(Predicted) | [density ]
1.393±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Light yellow | [InChIKey]
SFTHVDYRPHJAND-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Uses]
2-?Chloro-?1-?(3-?fluorobenzyloxy)?-?4-?nitrobenzene is a reagent used in the synthesis of novel indole-2-carboxamide derivative as anti-inflammatory agents used in the treatment of sepsis. Also an intermediate of Niraparib (N481400), a novel oral poly(ADP-ribose)polymerase (PARP) inhibitor efficacious in BRCA-1 and -2 mutant tumors. | [Synthesis]
Example 1a: General procedure for the synthesis of 3-chloro-4-(3-fluorobenzyloxy)nitrobenzene from 3-chloro-4-fluoronitrobenzene and 3-fluorobenzyl alcohol. First, 3-fluorobenzyl alcohol (0.30 kg, 2.39 mol, 1.05 eq.) was dissolved in acetonitrile (ACN, 6.0 L), followed by addition of potassium hydroxide flakes (85%, 0.16 kg, 1.25 eq.). The resulting suspension was heated to 35 °C. A solution of 3-chloro-4-fluoronitrobenzene (0.40 kg, 2.28 mol) dissolved in acetonitrile (ACN, 2.0 L) was slowly added in the temperature range of 35-40 °C. The reaction mixture was kept at this temperature for 18 hours. After completion of the reaction, the mixture was cooled to 20-25 °C and the reaction was quenched with water (8 L). The resulting slurry was filtered and the solid product was washed with water (2 x 0.40 L). Finally, the product was dried at 45 °C and 10 mmHg pressure for 25 h to give 0.59 kg of the target compound 3-chloro-4-(3-fluorobenzyloxy)nitrobenzene in 92% yield. | [References]
[1] Patent: US2006/270668, 2006, A1. Location in patent: Page/Page column 16
[2] Patent: US2006/270669, 2006, A1. Location in patent: Page/Page column 19-20
[3] Patent: WO2009/63054, 2009, A1. Location in patent: Page/Page column 37; 68
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8546 - 8555
[5] Patent: WO2011/2523, 2011, A1. Location in patent: Page/Page column 43 |
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