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[ CAS No. 317-46-4 ] {[proInfo.proName]}

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Chemical Structure| 317-46-4
Chemical Structure| 317-46-4
Structure of 317-46-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 317-46-4 ]

CAS No. :317-46-4 MDL No. :MFCD06797825
Formula : C7H4FNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :WLGUSLGYTNJJFV-UHFFFAOYSA-N
M.W : 185.11 Pubchem ID :18672992
Synonyms :

Calculated chemistry of [ 317-46-4 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.18
TPSA : 83.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.58
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 0.94
Log Po/w (SILICOS-IT) : -0.48
Consensus Log Po/w : 0.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.73 mg/ml ; 0.00936 mol/l
Class : Soluble
Log S (Ali) : -2.67
Solubility : 0.399 mg/ml ; 0.00216 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.43
Solubility : 6.85 mg/ml ; 0.037 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.74

Safety of [ 317-46-4 ]

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

Application In Synthesis of [ 317-46-4 ]

* 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 [ 317-46-4 ]
  • Downstream synthetic route of [ 317-46-4 ]

[ 317-46-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 445-29-4 ]
  • [ 7304-32-7 ]
  • [ 317-46-4 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 101
[2] Recueil des Travaux Chimiques des Pays-Bas, 1914, vol. 33, p. 336
  • 2
  • [ 437-86-5 ]
  • [ 317-46-4 ]
YieldReaction ConditionsOperation in experiment
62.8% With chromium(VI) oxide; sulfuric acid; acetic acid In water at 95℃; Alternative Method of Preparing methyl 3-amino-2-fluorobenzoate (Step B of Intermediate 15 Above); Step A: 2-fluoro-3-nitrobenzoic acid; Concentrated sulfuric acid (195 ml) was added carefully with stirring to a solution of 2-fluoro-3-nitrotoluene (100 g, 645 mmol) in acetic acid (1000 ml). The mixture was warmed up to 95° C. and the solution of chromium trioxide (226 g, 2.25 mol) in water (200 ml) was added dropwise with stirring over 2 h. After addition the mixture was heated with stirring for another 3 h, allowed to cool down to room temperature and poured into water (3 L). The mixture was extracted with ethyl acetate (3.x.1 L), the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford a light green solid, which was washed with dichloromethane (3.x.300 ml) and dried under vacuum to afford the title compound was obtained as a light yellow solid (75 g, 62.8percent). 1H NMR (300 MHz, DMSO) δ ppm 8.27 (m, 1H), 8.15 (m, 1H), 7.48 (m, 1H).
62.8% With chromium(VI) oxide; sulfuric acid; acetic acid In water at 95℃; for 2 h; Inert atmosphere Concentrated sulfuric acid (195 ml_) was added carefully with stirring to a solution of 2-fluoro-3-nitrotoluene (100 g, 645 mmol) in acetic acid (1000 ml_). The mixture was warmed up to 95 °C and a solution of chromium trioxide (226 g, 2.25 mol) in water (200 ml) was added dropwise with stirring over 2h. After addition the mixture was heated with stirring for another 3h, allowed to cool down to room temperature and poured into water (3 L). The mixture was extracted with ethyl acetate (3 x 1 L), the combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford a light green solid, which was washed with dichloromethane (3 x 300 ml_) and dried under vacuum to afford the title compound as a light yellow solid in the amount of 75 g (62.8percent yield). 1 H NMR(300MHz, DMSO) δ ppm 8.27 (m, 1 H), 8.15 (m, 1 H), 7.48 (m, 1 H).
Reference: [1] Patent: US2009/298815, 2009, A1, . Location in patent: Page/Page column 53
[2] Patent: WO2011/59610, 2011, A1, . Location in patent: Page/Page column 87-88
  • 3
  • [ 96516-29-9 ]
  • [ 317-46-4 ]
Reference: [1] Patent: WO2011/79133, 2011, A2, . Location in patent: Page/Page column 152
  • 4
  • [ 445-29-4 ]
  • [ 7304-32-7 ]
  • [ 317-46-4 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 101
[2] Recueil des Travaux Chimiques des Pays-Bas, 1914, vol. 33, p. 336
  • 5
  • [ 95-52-3 ]
  • [ 317-46-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1914, vol. 33, p. 336
[2] Bulletin des Societes Chimiques Belges, 1930, vol. 39, p. 101
  • 6
  • [ 67-56-1 ]
  • [ 317-46-4 ]
  • [ 946126-94-9 ]
YieldReaction ConditionsOperation in experiment
96% at 70℃; Step B: methyl 2-fluoro-3-nitrobenzoate; 2-Fluoro-3-nitrobenzoic acid (75 g) was dissolved in 300 ml of methanol, and then 20 ml of concentrated H2SO4 was added. The mixture was stirred at 70° C. overnight and cooled to rt, the resulting solid was filtered and washed with water (3.x.200 ml), to the filtered was added water (400 ml), the resulting precipitate was filtered and washed with water (2.x.100 ml) to afford another batch of product. The solid were combined and dried under vacuum to afford the title compound was obtained as a light yellow solid (78 g, 96percent).
96% at 70℃; for 1 h; Inert atmosphere 2-Fluoro-3-nitrobenzoic acid (75 g) was dissolved in 300 mL of methanol, and then 20 mL of concentrated H2SO was added. The mixture was stirred at 70 °C overnight and cooled to room temperature. The resulting solid was filtered and washed with water (3 x 200 mL), to the filtered was added water (400 mL), the resulting precipitate was filtered and washed with water (2 x 100 mL) to afford another batch of product. The solids were combined and dried under vacuum to afford the title compound as a light yellow solid in the amount of 78 g (96percent yield).
93% at 50℃; for 16 h; A solution of 2-fluoro-3-nitrobenzoic acid (5 g, 27.0 mmol) in MeOH (50 mL) was treated with concentrated H2S04 (1.4 mL, 27.0 mmol) and the resulting reaction was stirred at 50 °C for 16 h. The solvent was removed under reduced pressure and the residue was diluted with EtO Ac. The organic solution was washed with saturated aqueous NaHC03 solution until the water phase reached neutral pH. The two phases were separated. Organics were washed with water, brine and dried (Na2S04). The solution was filtered and concentrated to give crude methyl 2-fluoro-3-nitrobenzoate (5.1 g, 25.2 mmol, 93 percent) as a pale yellow solid which was used as is in the next step.[00102] LCMS (m/z): 258.1 (MH+), tR = 0.74 min; 1H NMR (400 MHz, CDC13,): δ ppm 4.00 (s, 3 H), 7.38 (t, J= 8.0 Hz, 1 H), 8.14 - 8.27 (m, 2 H).
91% at 70℃; A mixture of 2-fluoro-3-nitrobenzoic acid (7.5 g, 40.5 mmol) was added to methanol (30 mL) was added dropwise concentrated sulfuric acid (2mL), 70 °C reaction overnight.The system was cooled, suction filtered, washed with water and then suction filtered and the filtrate were combined residues dried under reduced pressure to give the product (7.3 g, 91percent yield).

Reference: [1] Patent: US2009/298815, 2009, A1, . Location in patent: Page/Page column 54
[2] Patent: WO2011/59610, 2011, A1, . Location in patent: Page/Page column 88
[3] Organic Letters, 2011, vol. 13, # 15, p. 3840 - 3843
[4] Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10612 - 10615
[5] Patent: WO2011/161216, 2011, A1, . Location in patent: Page/Page column 29
[6] Patent: CN103936728, 2016, B, . Location in patent: Paragraph 0211; 0216; 0217; 0218
  • 7
  • [ 317-46-4 ]
  • [ 946126-95-0 ]
Reference: [1] Patent: WO2008/104754, 2008, A1, . Location in patent: Page/Page column 171
  • 8
  • [ 317-46-4 ]
  • [ 914223-43-1 ]
Reference: [1] Patent: US2009/286783, 2009, A1, . Location in patent: Page/Page column 57-58
[2] Patent: US2009/306087, 2009, A1, . Location in patent: Page/Page column 44-45
[3] Patent: WO2011/63159, 2011, A1, . Location in patent: Page/Page column 197
[4] European Journal of Medicinal Chemistry, 2013, vol. 66, p. 450 - 465
  • 9
  • [ 317-46-4 ]
  • [ 1051899-73-0 ]
Reference: [1] Patent: WO2008/104754, 2008, A1,
  • 10
  • [ 317-46-4 ]
  • [ 1195768-19-4 ]
Reference: [1] Patent: CN103936728, 2016, B,
  • 11
  • [ 317-46-4 ]
  • [ 1154278-17-7 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 15, p. 3840 - 3843
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10612 - 10615
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