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[ CAS No. 1207453-90-4 ] {[proInfo.proName]}

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Chemical Structure| 1207453-90-4
Chemical Structure| 1207453-90-4
Structure of 1207453-90-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1207453-90-4 ]

CAS No. :1207453-90-4 MDL No. :MFCD22370184
Formula : C8H4FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :JBLFHMWQMPVDDL-UHFFFAOYSA-N
M.W : 197.12 Pubchem ID :57519176
Synonyms :

Calculated chemistry of [ 1207453-90-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.55
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.67
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 0.38
Consensus Log Po/w : 1.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.12
Solubility : 1.5 mg/ml ; 0.00759 mol/l
Class : Soluble
Log S (Ali) : -2.39
Solubility : 0.796 mg/ml ; 0.00404 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.24
Solubility : 1.13 mg/ml ; 0.00573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 1207453-90-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1207453-90-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 1207453-90-4 ]
  • Downstream synthetic route of [ 1207453-90-4 ]

[ 1207453-90-4 ] Synthesis Path-Upstream   1~5

  • 1
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YieldReaction ConditionsOperation in experiment
79% With water In 1,4-dioxane for 96 h; Reflux A mixture of methyl 5-fluoro-2-methyl-3-nitrobenzoate (28 g, 130.5 mmol), NBS (27.8 g, 156.6 mmol) and BPO (3.13 g, 13.1 mmol) in CCl4 (400 mL) was heated to reflux overnight. TLC (petroleum ether/EtOAc=15:1) showed the starting material was consumed completely. Water (200 mL) was added and CCl4 was removed under reduced pressure. The residue was extracted with DCM (200 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give crude methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, yield 94percent) as a brown oil. A mixture of methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, 123 mmol) in 1,4-dioxane (250 mL) and water (62.5 mL) was heated to reflux for 4 days. TLC (petroleum ether/EtOAc=15:1) showed the starting material was consumed completely. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL.x.4). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give crude product. The crude product was purified by gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1) to give 6-fluoro-4-nitroisobenzofuran-1(3H)-one (19.2 g, yield 79percent) as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.74 (s, 2H), 7.97-7.98 (dd, 1H), 8.24-8.27 (dd, 1H); LC-MS (ESI) m/z: 198(M+1)+
79% for 96 h; Reflux Example 63B6-Fluoro-4-nitroisobenzofuran- 1 (3H)-one[00598] A mixture of methyl 5-fluoro-2-methyl-3-nitrobenzoate (28 g, 130.5 mmol), NBS (27.8 g, 156.6 mmol) and BPO (3.13 g, 13.1 mmol) in CC14 (400 mL) was heated to reflux overnight. TLC (petroleum ether/ EtOAc = 15: 1) showed the starting material was consumed completely. Water (200 mL) was added and CC14 was removed under reduced pressure. The residue was extracted with DCM (200 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, concentrated to give crude methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, yield 94percent) as a brown oil. A mixture of methyl 2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate (36 g, 123 mmol) in 1, 4-dioxane (250 mL) and water (62.5 mL) was heated to reflux for 4 days. TLC (petroleum ether / EtOAc = 15: 1) showed the starting material was consumed completely. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine, dried over Na2S04, concentrated to give crude product. The crude product was purified by gel chromatography (petroleum ether to petroleum ether/ EtOAc = 5: 1) to give 6-fluoro-4- nitroisobenzofuran-l(3H)-one (19.2 g, yield 79percent) as a white solid. ^-NMR (400 MHz, CDC13) δ (ppm): 5.74 (s, 2H), 7.97-7.98 (dd, 1H), 8.24-8.27 (dd, 1H); LC-MS (ESI) m/z: 198(M+1)+.
2.3 g Reflux Amixtureofthecrudecompound5methyl2-(bromomethyl)-5-fluoro-2-methyl-3-nitrobenzoate(4.5g)in1,4-dioxane(15mL)andwater(3mL)washeatedtorefluxovernight.TLC(petroleumether/EtOAc=5:1)showedthestartingmaterialwasconsumedcompletely. Dioxanewasremovedunderreducedpressure.TheresiduewasextractedwithEtOAc(15mL×4).Thecombinedorganiclayerswerewashedwithbrine,driedoverNa 2SO 4,concentratedtogivethecrudeproduct.Thecrudeproductwaspurifiedbygelchromatography(petroleumethertopetroleumether/EtOAc=5/1)togivecompound6,6-fluoro-4-nitroisobenzofuran(2.3g,83.3percentyield,twosteps)asawhitesolid. 1HNMR(400MHz,CDCl 3):δ(ppm)8.25(dd,J=7.8,2.2Hz,1H),7.97(dd,J=6.0,2.0Hz,1H),5.12(d,J=2.0Hz,2H)
Reference: [1] Patent: US2010/35883, 2010, A1, . Location in patent: Page/Page column 1
[2] Patent: WO2011/130661, 2011, A1, . Location in patent: Page/Page column 122
[3] Patent: WO2018/153279, 2018, A1, . Location in patent: Paragraph 66
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Reference: [1] Patent: WO2011/130661, 2011, A1,
  • 3
  • [ 697739-03-0 ]
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Reference: [1] Patent: WO2011/130661, 2011, A1,
[2] Patent: WO2018/153279, 2018, A1,
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  • [ 850462-64-5 ]
  • [ 1207453-90-4 ]
Reference: [1] Patent: WO2011/130661, 2011, A1,
  • 5
  • [ 1207453-90-4 ]
  • [ 1207456-01-6 ]
  • [ 1207456-00-5 ]
Reference: [1] Patent: US2011/196153, 2011, A1,
[2] Patent: US2011/196153, 2011, A1,
[3] Patent: US2011/196153, 2011, A1,
[4] Patent: US2011/196153, 2011, A1,
[5] Patent: WO2013/28495, 2013, A1,
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