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[ CAS No. 845866-81-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 845866-81-1
Chemical Structure| 845866-81-1
Chemical Structure| 845866-81-1
Structure of 845866-81-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 845866-81-1 ]

CAS No. :845866-81-1 MDL No. :MFCD06657961
Formula : C7H4BrF3 Boiling Point : -
Linear Structure Formula :- InChI Key :WAJOYKZVIXCVTR-UHFFFAOYSA-N
M.W : 225.01 Pubchem ID :2761180
Synonyms :

Calculated chemistry of [ 845866-81-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.17
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
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) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 3.33
Log Po/w (WLOGP) : 4.46
Log Po/w (MLOGP) : 4.37
Log Po/w (SILICOS-IT) : 3.79
Consensus Log Po/w : 3.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.67
Solubility : 0.048 mg/ml ; 0.000214 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.222 mg/ml ; 0.000985 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0162 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 845866-81-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 845866-81-1 ]

* 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 [ 845866-81-1 ]

[ 845866-81-1 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 845866-81-1 ]
  • [ 68-12-2 ]
  • [ 1166820-28-5 ]
YieldReaction ConditionsOperation in experiment
36.8% The 2-difluoromethyl-5-fluorobenzaldehyde used as starting material was prepared as follows :-; Isopropylmagnesium chloride - lithium chloride complex (IM, 21.46 mL, 21.46 mmol) was added to 2-bromo-l-(difluoromethyl)-4-fluorobenzene (4.39 g, 19.51 mmol) in THF (120 mL) cooled to -200C under nitrogen. The resulting solution was stirred at -200C for 1 hour. N,N-Dimethylformamide (1.813 mL, 23.41 mmol) was added, and the mixture stirred for a further 1 hour, maintaining the temperature in the range -15 to -200C. The mixture was allowed to warm to ambient temperature, then 2M hydrochloric acid (100 mL) was added and the mixture was extracted with EtOAc (150 mL). The organic layer was washed with saturated sodium bicarbonate (120 mL) and concentrated to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 2- (difluoromethyl)-5-fluorobenzaldehyde (1.250 g, 36.8%) as a colourless liquid. IH NMR (399.9 MHz, CDC13) delta 7.26 (IH, t), 7.37 - 7.43 (IH, m), 7.63 - 7.67 (IH, m), 7.78 - 7.82 (IH, m), 10.19 (IH, d); m/z = 173 [M-H]-.
  • 2
  • [ 845866-81-1 ]
  • [ 1402601-93-7 ]
  • [ 1402602-07-6 ]
  • 3
  • [ 845866-81-1 ]
  • 1-(2-(difluoromethyl)-5-fluorophenyl)ethanol [ No CAS ]
  • 4
  • [ 845866-81-1 ]
  • 2-(1-bromoethyl)-1-(difluoromethyl)-4-fluorobenzene [ No CAS ]
  • 5
  • [ 845866-81-1 ]
  • [ 78191-00-1 ]
  • 1-(2-(difluoromethyl)-5-fluorophenyl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Step 2: 1-(2-(difluoromethyl)-5-fluorophenyl)ethanone 1-Bromo-2-(difluoromethyl)-5-fluorobenzene(8.36 g, 37.5 mmol) was dissolved in anhydrous ether (100 mL), cooled to -78 C, and then 2.4 M n-butyllithium (18.7 mL, 45 mmol) was added dropwise under a nitrogen atmosphere. The resultant was stirred for 1 hour. While the temperature was kept at -78C, N-methyl-N-methoxylacetamide (7.73 g, 75 mmol) was added, and the resultant was then stirred for 2 hours. After the resultant was warmed up to room temperature, it was washed with saturated brine and extracted with ethyl acetate. The extract was dried, concentrated, and purified by silica gel column chromatography to give 1-(2-(difluoromethyl)-5-fluorophenyl)ethanone (4.2 g, 60% yield). 1H-NMR (400 MHz, CDCl3): delta= 7.45-7.40 (m, 1H), 7.31-7.27 (m, 1H), 7.20-7.12 (m,1H), 6.78-6.50 (t, J= 56 Hz, 1H), 2.42 (s, 3H).
  • 6
  • [ 59142-68-6 ]
  • [ 845866-81-1 ]
YieldReaction ConditionsOperation in experiment
93% With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 0℃;Reflux; Step 1: 1-bromo-2-difluoromethyl-5-fluorobenzene 2-Bromo-4-fluorobenzaldehyde (8.04 g, 40 mmol) was added in CH2Cl2 (80 mL), cooled to 0C, and then diethylaminosulphurtrifluoride (DAST) (7.96 mL, 60 mmol) was added dropwise. The resultant was stirred at low temperature for 30 minutes, and then refluxed overnight. The reaction was quenched with ethanol, washed with water, dried, concentrated, and purified by silica gel column chromatography to give 1-bromo-2-(difluoromethyl)-5-fluorobenzene (8.36 g, 93% yield). 1H-NMR (400 MHz, CDCl3):delta= 7.579 (m, 1H), 7.385 (m, 1H), 7.091 (m, 1H),35 6.993-6.720 (t, J = 54.6 Hz, 1H).
With diethylamino-sulfur trifluoride; In dichloromethane; at 20℃; To a solution of 2-bromo-4-fluorobenzaldehyde (3.00 g, 14.9 mmol) in DCM (30 mL) at 0 C was added DAST (5.98 g, 37.1 mmol) and the mixture was stirred at rt overnight. Aqueous NaHCOs was added and the aqueous layer was extracted with DCM (3 x 50 mL). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography on silica gel (PE/EtOAc = 10:1 ) to give the title compound as a yellow oil.
  • 7
  • [ 845866-81-1 ]
  • [ 73183-34-3 ]
  • 2-(2-(difluoromethyl)-5-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 85℃;Inert atmosphere; A mixture of 2-bromo-1 -(difluoromethyl)-4-fluorobenzene (73 g, 0.287 mol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane) (88 g, 0.345 mol), Pd(dppf)CI2 (10.4 g, 0.014 mol) and KOAc (95.8 g, 0.978 mol) in 1 ,4-dioxane (700 mL) and DMSO (30 mL) was stirred at 85 C under N2 overnight. The mixture was quenched with water (250 mL) and extracted with EtOAc (3 x 500 mL). The combined organic layers were washed with brine, dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by flash chromatography column on silica gel eluting with PE to give the title compound as a yellow oil.
  • 8
  • [ 845866-81-1 ]
  • 2-(difluoromethyl)-5-fluorobenzoic acid [ No CAS ]
  • 9
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 845866-81-1 ]
  • methyl 2-(difluoromethyl)-5-fluorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.08 g With palladium diacetate; triethylamine; 1,3-bis(phenylphosphano)propane; In methanol; N,N-dimethyl-formamide; at 70℃; under 760.051 Torr; for 24h; To <strong>[845866-81-1]2-bromo-1-(difluoromethyl)-4-fluorobenzene</strong> (4.95 g) were added DMF (50 mL), MeOH (10 mL), and TEA (10 mL). Pd(OAc)2 (0.494 g) and DPPP (0.907 g) were added thereto, and the mixture was stirred under carbon monoxide atmosphere at 1 atm at 70C for 24 hours. Then, water and AcOEt were added thereto, and insoluble substances were filtered. Water was added to the filtrate and the mixture was extracted with AcOEt. The organic layer was washed with brine, dried over anhydrous Na2SO4, and then filtered, and the filtrate was concentrated under reduced pressure to give methyl 2-(difluoromethyl)-5-fluorobenzoate (2.08 g).
  • 10
  • [ 845866-81-1 ]
  • methyl 2-(difluoromethyl)-5-fluorobenzoate [ No CAS ]
  • 11
  • [ 845866-81-1 ]
  • copper(l) cyanide [ No CAS ]
  • 2-(difluoromethyl)-5-fluorobenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 110℃; for 48h; To a solution of 2-bromo-1 -(difluoromethyl)-4-fluorobenzene (Int 20b) (2.89 g, 12.9 mmol) in DMF (30 ml_) was added CuCN (6.61 g, 38.8 mmol) and the mixture was stirred at 1 10 C for 2 d. The mixture was filtered. To the filtrate was added water (50 ml_) and the mixture was extracted with EtOAc (3 x 40 ml_). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated to dryness. The residue was purified by column chromatography on silica gel (PE/EtOAc = 10:1 ) to give the title compound as a yellow oil.
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