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[ CAS No. 1089280-66-9 ] {[proInfo.proName]}

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Chemical Structure| 1089280-66-9
Chemical Structure| 1089280-66-9
Structure of 1089280-66-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1089280-66-9 ]

CAS No. :1089280-66-9 MDL No. :MFCD11847613
Formula : C7H5ClFNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :WGZSTQPRYUSALF-UHFFFAOYSA-N
M.W : 205.57 Pubchem ID :53403289
Synonyms :

Calculated chemistry of [ 1089280-66-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.72
TPSA : 55.05 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.45
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 2.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.87
Solubility : 0.279 mg/ml ; 0.00136 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.116 mg/ml ; 0.000563 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.81
Solubility : 0.321 mg/ml ; 0.00156 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 1089280-66-9 ]

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 [ 1089280-66-9 ]

* 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 [ 1089280-66-9 ]
  • Downstream synthetic route of [ 1089280-66-9 ]

[ 1089280-66-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 345-25-5 ]
  • [ 74-88-4 ]
  • [ 1089280-66-9 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 60 h; To a solution of 4-chloro-5-fluoro-2-nitrophenol (10.00 g, 52.21 mmol) in dry DMF(50 mL), K2C03 was added (11.00, 79.60 mmol), followed by iodomethane (4.00 mL,64.25 mmol) and the resulting suspension was stirred at rt for 2.5 days. The resultingdark orange suspension was concentrated in vacuo to remove the DMF solvent, and the residue partitioned between EtOAc (300 mL) and iN HC1 (100 mL). The resulting wasseparated and the organic layer washed successively with 1M NaOH (100 mL), water(100 mL) and brine (100 mL), dried over Na2SO4, filtered and evaporated to give 10.34g of intermediate 86 (96percent yield, dark orange solid).
89% With potassium carbonate In N,N-dimethyl-formamide at 20℃; 4-Chloro-5-fluoro-2-nitrophenol (2.29 g, 12.0 mmol) was dissolved in DMF (25 mL). K2CO3 (2.5 g, 18 mmol) and iodomethane (0.893 mL, 14.3 mmol) were added and the mixture was stirred at rt overnight. The mixture was then poured into H2O and extracted with EtOAc (2.x.) and then the combined organics were extracted with H2O (5.x.). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to give the title compound of step B without further purification (2.19 g, 89percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.22 (dd, J=7.8, 1.0 Hz, 1H), 7.54 (d, J=11.4 Hz, 1H), 3.90 (d, J=1.1 Hz, 3H).
Reference: [1] Patent: WO2017/125530, 2017, A1, . Location in patent: Page/Page column 261; 262
[2] Patent: US2008/300242, 2008, A1, . Location in patent: Page/Page column 114-115
  • 2
  • [ 501-29-1 ]
  • [ 1089280-66-9 ]
YieldReaction ConditionsOperation in experiment
75% at 0℃; for 2 h; To 1- chloro-2-fluoro-4-methoxybenzene (5.00 g, 31.2 mmol) in cone. H2SO4 (30 mL) at -10 °C to 0 °C, potassium nitrate (3.47 g, 34.4 mmol) was added portionwise to the reaction mixture. The reaction was stirred at 0 °C for 2 h. The reaction was quenched with iced water and filtered. The obtained solids were recrystallized with hexanes to give Intermediate 15A (4.8 g, 75percent).
70% at 0℃; for 2 h; To a mixture of 1-chloro-2-fluoro-4-methoxybenzene (5.00 g, 31.1 mmol) in cone. H2S04 (30 mL) at 0-10eC was added portionwise potassium nitrate (3.78 g, 37.4 mmol) and the reaction was stirred at OeC for 2 h. The reaction was quenched with ice water and filtered. The obtained solids were recrystallized with hexanes to give 4.50 g 3 (70percent) of 1-chloro-2-fluoro-4-methoxy-5-nitrobenzene. 1HNMR (400 MHz, DMSO- d6) U8.30 (d, J = 2.0 Hz, 1H), 7.61 (d, J = 2.3 Hz, 1H), 3.96 (s, 3H); ESI-MS (m/z) 205.76 (MH)+.
Reference: [1] Patent: WO2014/22349, 2014, A1, . Location in patent: Paragraph 00194
[2] Patent: WO2018/20474, 2018, A1, . Location in patent: Page/Page column 155
  • 3
  • [ 67-56-1 ]
  • [ 1481-68-1 ]
  • [ 1089280-66-9 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃;
To a mixture of potassium tert-butoxide (3.0 g, 26.9 mmol) in DMF (20 mL), methanol (0.79 g, 24.8 mmol) was added at 0°C. The reaction mixture was stirred at 0°C for 15 minutes then a solution of 1-chloro-2,4-difluoro-5-nitrobenzene (4.0 g, 20.7 mmol) in DMF (20 mL) was added at 0 °C and the reaction mass stirred for 3 hours at room temperature. Water (200 mL) was added to the reaction mixture and reaction mass was extracted with EtOAc (3 x 50 mL). The combined organic extracts were washed with water (80 mL), brine (80 mL), dried (Na2S04) and concentrated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 20-25 percent EtOAc in hexane to give the desired product (3 g, 71percent) as a solid.
Reference: [1] Patent: WO2011/141716, 2011, A2, . Location in patent: Page/Page column 92
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