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[ CAS No. 156573-09-0 ] {[proInfo.proName]}

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Chemical Structure| 156573-09-0
Chemical Structure| 156573-09-0
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Product Details of [ 156573-09-0 ]

CAS No. :156573-09-0 MDL No. :MFCD07368018
Formula : C8H7BrF2O Boiling Point : -
Linear Structure Formula :- InChI Key :OJZVBJOHBGYINN-UHFFFAOYSA-N
M.W : 237.04 Pubchem ID :26985491
Synonyms :

Calculated chemistry of [ 156573-09-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.36
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.15
Log Po/w (WLOGP) : 3.97
Log Po/w (MLOGP) : 3.71
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 3.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.53
Solubility : 0.0696 mg/ml ; 0.000294 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.23 mg/ml ; 0.000969 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.35
Solubility : 0.0107 mg/ml ; 0.000045 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 156573-09-0 ]

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 [ 156573-09-0 ]

* 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 [ 156573-09-0 ]
  • Downstream synthetic route of [ 156573-09-0 ]

[ 156573-09-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 74-96-4 ]
  • [ 144292-32-0 ]
  • [ 156573-09-0 ]
YieldReaction ConditionsOperation in experiment
97% With tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 6 h; Inert atmosphere To an aqueous (400 ml) solution of 4-bromo-2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (hereinafter, abbreviated as TBAB) (24.2 g), sodium hydroxide (75.9 g) was added, and heating agitation was carried out at 80° C for 6 hours in a nitrogen atmosphere.
After completion of the reaction, extraction was carried out with heptane, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a black oily matter was obtained.
The resultant material was purified by distillation, and thus 1-ethoxy-2,3-difluorobromobenzene (T-2) was obtained as a colorless oily matter (230.0 g, yield: 97percent).
97% With tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 6 h; Inert atmosphere To a water (400 ml) solution of 4-bromo-2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (hereinafter referred to as TBAB) , Sodium hydroxide (75.9 g) were added, and the mixture was heated and stirred at 80 ° C. for 6 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with heptane. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a black oil. This product was purified by distillation to give 1-ethoxy-2,3-difluorobromobenzene (T-2) as a colorless oil (230.0 g, yield 97percent).
Reference: [1] Patent: EP2484658, 2012, A1, . Location in patent: Page/Page column 37
[2] Patent: JP5663957, 2015, B2, . Location in patent: Paragraph 0137-0138; 0139
  • 2
  • [ 74-96-4 ]
  • [ 156573-09-0 ]
Reference: [1] Patent: US2011/291047, 2011, A1,
  • 3
  • [ 64-67-5 ]
  • [ 144292-32-0 ]
  • [ 156573-09-0 ]
Reference: [1] Synlett, 2011, # 9, p. 1273 - 1276
  • 4
  • [ 156573-09-0 ]
  • [ 121-43-7 ]
  • [ 212386-71-5 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 2 h; Inert atmosphere
Stage #2: at -70 - 20℃; for 16 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
According to the synthetic scheme shown above, compound (T-2) (129.5 g) obtained as an intermediate of Example 1 was dissolved in DryTHF (500 ml), and the resultant solution was cooled to -70°C. In a nitrogen atmosphere, n-BuLi (500 ml) was added dropwise, and agitation was carried out at -70°C for 2 hours.
Then, a DryTHF solution of trimethyl borate (129.5 g) was slowly added dropwise at -70°C, and the resultant solution was heated to room temperature and agitated for 16 hours.
After completion of the reaction, 2N-HCl (200 ml) was added, and then extraction was carried out with toluene, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a light brown solid was obtained.
The resultant material was subjected to recrystallization (heptane: toluene = 4 : 1 in a volume ratio), and thus (T-20) was obtained as a colorless crystal (117.2 g, yield: 71percent).
71%
Stage #1: With n-butyllithium In tetrahydrofuran at -70℃; for 2 h; Inert atmosphere
Stage #2: at -70 - 20℃; for 16 h; Inert atmosphere
The compound (T-2) obtained in the above step(129.5 g) was dissolved in Dry THF (500 ml)It was cooled to -70 ° C.N-BuLi (500 ml) was added dropwise under a nitrogen atmosphere, and the mixture was stirred at -70 ° C. for 2 hours. Thereafter, a Dry THF solution of trimethyl borate (129.5 g) was slowly added dropwise at -70 ° C., the temperature was raised to room temperature, and the mixture was stirred for 16 hours.After completion of the reaction, 2N HCl (200 ml) was added and the mixture was extracted with toluene, washed with water and saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a light brown solid.This product was recrystallized (heptane: toluene = 4: 1 by volume ratio) to obtain (T-20) as colorless crystals (117.2 g, yield 71percent).
Reference: [1] Patent: EP2484658, 2012, A1, . Location in patent: Page/Page column 42
[2] Patent: JP5663957, 2015, B2, . Location in patent: Paragraph 0137-0138; 0140
[3] Patent: US2009/278089, 2009, A1, . Location in patent: Page/Page column 13
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