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[ CAS No. 221220-99-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 221220-99-1
Chemical Structure| 221220-99-1
Chemical Structure| 221220-99-1
Structure of 221220-99-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 221220-99-1 ]

CAS No. :221220-99-1 MDL No. :MFCD12910487
Formula : C6H3BrF2O Boiling Point : -
Linear Structure Formula :- InChI Key :GYKSRTXLESCBRM-UHFFFAOYSA-N
M.W : 208.99 Pubchem ID :18371110
Synonyms :

Calculated chemistry of [ 221220-99-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.08
TPSA : 20.23 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) : -5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 3.27
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 2.9
Consensus Log Po/w : 2.71

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.155 mg/ml ; 0.000742 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.619 mg/ml ; 0.00296 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.121 mg/ml ; 0.000577 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 221220-99-1 ]

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 [ 221220-99-1 ]

* 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 [ 221220-99-1 ]

[ 221220-99-1 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 348-57-2 ]
  • [ 221220-99-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,4-difluorobromobenzene With N-(1-methylethyl)-2-propanamine lithium salt In tetrahydrofuran at -78 - -65℃; for 2h; Stage #2: With tert.-butylhydroperoxide at -65 - 20℃; EXAMPLE C 3-Hydroxy-2,4-difluoro-bromobenzene 3-Hydroxy-2,4-difluoro-bromobenzene A quantity of 40.2 ml of 2.0 M lithium diisopropylamine (LDA) is dissolved in 80 ml of TIF at -78° C. and 15.4 g of 2,4-difluorobromobenzene is added keeping the temperature below -65° C. The reaction is stirred at -65° C. for 2 hours and 6.6 ml of 6 M anhydrous t-butyl hydroperoxide is added. After warming at room temperature, 100 ml of water is added and the mixture acidified. The solvent is removed by evaporation and the aqueous layer extracted with ether. The extracts are dried and then concentrated to give the desired product.
  • 2
  • [ 221220-99-1 ]
  • [ 74-88-4 ]
  • [ 221221-00-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In dichloromethane; acetone P.C 3-Methoxy-2,4-difluoro-bromobenzene 3-Methoxy-2,4-difluoro-bromobenzene A quantity of 3.7 g of 3-hydroxy-2,4-difluoro-bromobenzene is dissolved in 25 ml of acetone and 2.5 g of potassium carbonate is added followed by 2.2 ml of methyl iodide. The mixture is stirred at 20° C. for 6 hours and the solvent evaporated. After addition of dichloromethane, the suspension is filtered. Evaporation of the solvent affords the desired product.
With potassium carbonate In acetone at 20℃; for 6h; EXAMPLE C 3-Methoxy-2,4-difluoro-bromobenzene 3-Methoxy-2,4-difluoro-bromobenzene A quantity of 3.7 g of 3-hydroxy-2,4-difluoro-bromobenzene is dissolved in 25 ml of acetone and 2.5 g of potassium carbonate is added followed by 2.2 ml of methyl iodide.. The mixture is stirred at 20° C. for 6 hours and the solvent evaporated.. After addition of dichloromethane, the suspension is filtered.. Evaporation of the solvent affords the desired product.
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; Cooling with ice; D-8 4-bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine General procedure: To a mixture of 4-bromo-1H-pyrazolo[3,4-c]pyridine (CAS: 1032943-43-3) (262 mg), cesium carbonate (863 mg) and DMF (6.5 mL) was added dropwise methyl iodide (CAS: 74-88-4) (0.107 mL) under ice-cooling. The mixture was stirred at room temperature for 20 hr, water was added to the reaction solution under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (chloroform/methanol) to give the title compound (160 mg) as an oil. 1H-NMR (CDCl3) δ: 4.21 (3H, s), 8.06 (1H, s), 8.40 (1H, s), 8.89 (1H, s). MS (m/z): 212, 214 (M+H)+.
  • 3
  • [ 348-57-2 ]
  • [ 4111-54-0 ]
  • [ 221220-99-1 ]
YieldReaction ConditionsOperation in experiment
With tert.-butylhydroperoxide In tetrahydrofuran; water P.C 3-Hydroxy-2,4-difluoro-bromobenzene PRECURSOR EXAMPLE C 3-Hydroxy-2,4-difluoro-bromobenzene A quantity of 40.2 ml of 2.0 M lithium diisopropylamine (LDA) is dissolved in 80 ml of THF at -78° C. and 15.4 g of 2,4-difluorobromobenzene is added keeping the temperature below -65° C. The reaction is stirred at -65° C. for 2 hours and 6.6 ml of 6 M anhydrous t-butyl hydroperoxide is added. After warming to room temperature, 100 ml of water is added and the mixture acidified. The solvent is removed by evaporation and the aqueous layer extracted with ether. The extracts are dried and then concentrated to give the desired product.
  • 4
  • [ 221220-99-1 ]
  • 2',4'-difluoro-3'-methoxy[1,1'-biphenyl]-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C / Cooling with ice 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / water; 1,4-dioxane / 4 h / 70 °C
  • 5
  • [ 221220-99-1 ]
  • [ 73183-34-3 ]
  • 2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 100℃; for 3h; Synthesis of 2,6-difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (Intermediate D1) [00198] To a mixture of 3-bromo-2,6-difluorophenol (300 mg, 1.44 mmol), bis(pinacolato)diboron (401 mg, 1.58 mmol) and Pd(dppf)Cl2 (52 mg, 72 μmol) in 1,4-dioxane (15 mL) was added potassium acetate (423 mg, 4.31 mmol). The mixture was heated to 100°C and stirred for 3h. The mixture was cooled to rt and filtered. The filtrate was concentrated in vacuo to afford crude Intermediate D1 (300 mg, 82% yield), which was used without further purification. TLC: Pet. ether/EtOAc=3/1 (v/v), Rf=0.90.
  • 6
  • [ 221220-99-1 ]
  • 3',5'-dichloro-2,4-difluoro-4'-(2-fluoro-4-hydroxy-3-isopropylbenzyl)-[1,1'-biphenyl]-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / 1,4-dioxane / 3 h / 100 °C 2: Sodium hydrogenocarbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / water monomer; 1,4-dioxane / 80 °C / Inert atmosphere
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