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[ CAS No. 203059-80-7 ] {[proInfo.proName]}

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Chemical Structure| 203059-80-7
Chemical Structure| 203059-80-7
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Product Details of [ 203059-80-7 ]

CAS No. :203059-80-7 MDL No. :MFCD00070789
Formula : C8H8F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WWAOVLXLTJXDGS-UHFFFAOYSA-N
M.W : 174.14 Pubchem ID :853175
Synonyms :

Calculated chemistry of [ 203059-80-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.34
TPSA : 18.46 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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 2.06
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 2.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.61 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.46 mg/ml ; 0.00838 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.21
Solubility : 0.108 mg/ml ; 0.000621 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 203059-80-7 ]

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 [ 203059-80-7 ]

* 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.

  • Downstream synthetic route of [ 203059-80-7 ]

[ 203059-80-7 ] Synthesis Path-Downstream   1~19

  • 2
  • [ 203059-80-7 ]
  • [ 246029-17-4 ]
YieldReaction ConditionsOperation in experiment
With sodium thiomethoxide In N,N-dimethyl-formamide at 20℃; for 2h; 5 Preparation 54,5-DIFLUORO-2-METHOXYPHENOLTo a solution of 1 ,2-difluoro-4,5-dimethoxybenzene (5 g, 28.7 mmol) in DMF (14 ml) was added sodium thiomethoxide (6.2 g, 88.5 mmol). After 30 min more DMF (4 ml) was added. The mixture was stirred in room temperature for 1 h 30 min and cooled on an icebath. Water was added and then HCI (10% in H2O). The solution was extracted with EtOAc and the combined organic phases were washed with water, dried (MgSO4) and evaporated to dryness with EtOH. Purification on flash column chromatography (Isooctane/EtOAc) gave the title compound (1.5 g). MS m/z (rel. intensity, 70 eV) 160 (M+, 82) 145 (bp), 117 (63), 97 (8), 88 (9).
Stage #1: 1,2-difluoro-4,5-dimethoxybenzene With sodium thiomethoxide In N,N-dimethyl-formamide at 100℃; for 6h; Stage #2: In ethyl acetate 28.i Sodium thiomethoxide (0.4g) was added to a solution of 1, 2-difluoro-4,5- dimethoxybenzene (1. OG) in DMF (LOML) at RT, then heated at 100°C for 4h. A further 0. 8G of sodium thiomethoxide was added, the mixture heated for a further 2H. The mixture was cooled, partitioned between ethylacetate/2M hydrochloric acid, the organics dried and evaporated under reduced pressure, yield 1. 05g
  • 3
  • [ 15448-47-2 ]
  • [ 203059-80-7 ]
  • [ 1188412-61-4 ]
YieldReaction ConditionsOperation in experiment
19% Stage #1: 1,2-difluoro-4,5-dimethoxybenzene With sec.-butyllithium In tetrahydrofuran; cyclohexane at -78 - 70℃; Stage #2: (R)-propylene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether; cyclohexane at -105 - -90℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; diethyl ether; cyclohexane at -90 - 0℃; 1 A solution of 1,2-difluoro-4,5-dimethoxybenzene (3.48 g, 20 mmol) in 10 mL of anhydrous THF was slowly added to a cooled at -78 °C solution of sec-BuLi in THF/cyclohexane (1.4M in cyclohexane, 15 mL, 21 mmol mixed with 80 mL of THF). The mixture was stirred at - 70 °C for 10 min, then a solution of R-(+)-propylene oxide (1.51 g, 1.8 mL, 26 mmol) in 15 mL of THF was added dropwise at -100 °C to -90 °C, then the mixture was cooled to -105 °C and a 46.5% solution of BF3 in diethyl ether (4.18 mL, 30 mmol) was added dropwise. The mixture was stirred at -100 °C to -90 °C for 2 h, then the reaction was quenched with 20 mL of sat. aq. NH4Cl at -90 °C. The mixture was stirred and warmed to 0 °C overnight. Then 20 mL of water was added and mixture was extracted with EtOAc (2x60 mL), the extract was dried over Na2SO4 and evaporated to give crude oil, which was purified by column (silicagel, EtOAc/hexane 1 :9, Rf = 0.29 in EtOAc/hexane 3:7) to give (2R)-1-(2,3-difluoro-5,6-dimethoxyphenyl)propan-2-ol (883 mg, 19 %) as pale oil. 1H NMR (300 MHz, CDCl3): δ 6.65 (m, 1H), 4.06 (m, 1H), 3.83 (s, 3H), 3.82 (s, 3H), 2.87 (m, 2H), 2.05 (d, J = 4.71 Hz, 1H), 1.25 (d, J = 6.24 Hz, 3H).
  • 4
  • [ 90076-65-6 ]
  • [ 203059-80-7 ]
  • Li(1+)*C2F6NO4S2(1-)*2C8H8F2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% at 20 - 150℃; Inert atmosphere;
  • 5
  • [ 203059-80-7 ]
  • [ 1188412-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / -78 - 70 °C 1.2: -105 - -90 °C 1.3: -90 - 0 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C 4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h
  • 6
  • [ 203059-80-7 ]
  • C11H15F2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / -78 - 70 °C 1.2: -105 - -90 °C 1.3: -90 - 0 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C 3.1: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C
  • 7
  • [ 203059-80-7 ]
  • [ 1188413-06-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / -78 - 70 °C 1.2: -105 - -90 °C 1.3: -90 - 0 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / -10 - 20 °C
  • 8
  • [ 203059-80-7 ]
  • [ 1193392-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux 3: hydrogen bromide / 3 h / 105 °C / Cooling on icebath 4: potassium hydroxide / ethanol / 5.5 h / Reflux
  • 9
  • [ 203059-80-7 ]
  • [ 1193392-74-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux
  • 10
  • [ 203059-80-7 ]
  • [ 1193392-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux 3: hydrogen bromide / 3 h / 105 °C / Cooling on icebath
  • 11
  • [ 203059-80-7 ]
  • [ 1193391-72-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux 3: hydrogen bromide / 3 h / 105 °C / Cooling on icebath 4: potassium hydroxide / ethanol / 5.5 h / Reflux 5: triethylamine / dichloromethane / 20 °C 6: acetonitrile / 0.33 h / 140 °C / Microwave irradiation
  • 12
  • [ 203059-80-7 ]
  • [ 1193392-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux 3: hydrogen bromide / 3 h / 105 °C / Cooling on icebath 4: potassium hydroxide / ethanol / 5.5 h / Reflux 5: triethylamine / dichloromethane / 20 °C 6: acetonitrile / 0.25 h / 140 °C / Microwave irradiation
  • 13
  • [ 203059-80-7 ]
  • [ 1193391-73-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sodium thiomethoxide / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium hydroxide / ethanol; water / 1.75 h / Reflux 3: hydrogen bromide / 3 h / 105 °C / Cooling on icebath 4: potassium hydroxide / ethanol / 5.5 h / Reflux 5: triethylamine / dichloromethane / 20 °C
  • 14
  • [ 33513-42-7 ]
  • [ 203059-80-7 ]
  • 2,3-difluoro-5,6-dimethoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1,2-difluoro-4,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 1h; A.1.64.5 A. 1.64.5. 2,3-Difluoro-5,6-dimethoxybenzaldehyde To a cooled (-78°C) solution of 1,2-difluoro-4,5-dimethoxybenzene (4.00 g, 23.00 mmol) in anh. THF (80 mL) is added a solution of BuLi (2.5 M in hexanes, 10.10 mL, 25.25 mmol) and the RM is further stirred at - 78°C, under nitrogen, for lh. Anh. DMF (2.67 mL, 34.50 mmol) is then added to the previous mixture and stirring at -78°C is continued for lh. The RM is then treated dropwise with sat. aq. NH4CI (50 mL) and is allowed to warm-up to RT. Water (50 mL) and EtOAc (100 mL) are then added and the layers areseparated. The aq. layer is further extracted with EtOAc (100 mL) and the combined organic layers are washed with water, dried over anh. MgSO4, filtered and concentrated under reduced pressure affording 2,3- difluoro-5,6-dimethoxybenzaldehyde as a yellow solid (4.72 g, quantitative). LC-MS A: tR = 0.77 mm; [M+H] = 203.08.
98% Stage #1: 1,2-difluoro-4,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78℃; for 3h; B.B.1.B.1.8.B.1.8.5 B.1.8.5. 2,3-Difluoro-5,6-dimethoxybenzaldehyde To a cooled (-78°C) solution of 1,2-difluoro-4,5-dimethoxybenzene (1.00 g, 5.74 mmol) in anh. THF (20 mL) is added dropwise a solution of n-butyllithium (2.5 M in hexanes, 2.53 mL, 6.32 mmol) and the RM is further stirred at -78°C, under nitrogen, for 1 h. Anh. DMF (0.667 mL, 8.61 mmol) is then added dropwise to the previous mixture and stirring at -78°C is continued for 3h. The RM is treated carefully with sat. aq. NH4CI (50 mL). Water (50 mL) and EtOAc (100 mL) are then added and the layers are separated. The aq. layer is further extracted with EtOAc and the combined organic layers are dried over anh. MgSC>4, filtered and concentrated to dryness under reduced pressure affording 2,3-difluoro-5,6-dimethoxybenzaldehyde as a yellow solid (1.14 g, 98%). LC-MS A: tR = 0.77 min; [M+H]+ = 203.10.
  • 15
  • [ 203059-80-7 ]
  • 2,3-difluoro-6-hydroxy-5-methoxybenzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 3 h / -78 °C 2.1: boron trichloride / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere 2.2: 1.5 h / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: boron tribromide / dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere
  • 16
  • [ 203059-80-7 ]
  • 4,5-difluoro-7-methoxy-2-methylbenzofuran-6-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: boron tribromide / dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere 3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 4.1: sodium hydroxide; water / methanol / 3 h / 50 °C 5.1: acetic anhydride; sodium acetate / 16 h / 150 °C / Inert atmosphere 5.2: 1 h / 20 °C 6.1: tin(IV) chloride / dichloromethane / 3.25 h / 0 - 20 °C / Inert atmosphere
  • 17
  • [ 203059-80-7 ]
  • 4,5-difluoro-7-methoxy-2-methylbenzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: boron tribromide / dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere 3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 4.1: sodium hydroxide; water / methanol / 3 h / 50 °C 5.1: acetic anhydride; sodium acetate / 16 h / 150 °C / Inert atmosphere 5.2: 1 h / 20 °C
  • 18
  • [ 203059-80-7 ]
  • ethyl 2-(3,4-difluoro-2-formyl-6-methoxyphenoxy)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: boron tribromide / dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere 3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere
  • 19
  • [ 203059-80-7 ]
  • 2-(3,4-difluoro-2-formyl-6-methoxyphenoxy)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: boron tribromide / dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere 3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 80 °C / Inert atmosphere 4.1: sodium hydroxide; water / methanol / 3 h / 50 °C
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