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[ CAS No. 87789-47-7 ] {[proInfo.proName]}

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Chemical Structure| 87789-47-7
Chemical Structure| 87789-47-7
Structure of 87789-47-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 87789-47-7 ]

CAS No. :87789-47-7 MDL No. :MFCD00236236
Formula : C7H6F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BNHAYQSUBZKWAG-UHFFFAOYSA-N
M.W : 160.12 Pubchem ID :2774124
Synonyms :

Calculated chemistry of [ 87789-47-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 35.06
TPSA : 29.46 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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 2.83
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : 1.75
Consensus Log Po/w : 2.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.7
Solubility : 0.321 mg/ml ; 0.002 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.257 mg/ml ; 0.0016 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.16
Solubility : 1.11 mg/ml ; 0.00695 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.38

Safety of [ 87789-47-7 ]

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 [ 87789-47-7 ]

* 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 [ 87789-47-7 ]

[ 87789-47-7 ] Synthesis Path-Downstream   1~26

YieldReaction ConditionsOperation in experiment
a Hydroquinone monodifluoromethyl ether A solution of 25.0 g of the product from Example 4 in 100 ml of THF is hydrogenated at room temperature and atmospheric pressure, using 8 g of Pd/C (5% Pd) as catalyst. The catalyst is filtered off, and the filtrate is evaporated.
  • 2
  • [ 87789-47-7 ]
  • [ 177596-30-4 ]
  • (4-difluoromethoxyphenyl) trans-4-n-heptyl-4-silacyclohexanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 12 Preparation of (4-difluoromethoxyphenyl) trans-4-n-heptyl-4-silacyclohexanecarboxylate The general procedure of Example 3 was repeated using <strong>[87789-47-7]4-difluoromethoxyphenol</strong> and 4-n-heptyl-4-phenyl-4-silacyclohexanecarboxylic acid, thereby obtaining the intended product.
  • 3
  • 1-(difluoromethoxy)-4-(tert.-butoxy)-benzene [ No CAS ]
  • [ 87789-47-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In ethanol; water; b) 30 g of 1-(difluoromethoxy)-4-(tert.-butoxy)benzene from Example 4a), 200 ml of ethanol, 50 ml of water and 10 ml of concentrated sulfuric acid were stirred at 80 C. for 2 hours. The reaction mixture was extracted with ether, the organic phase was dried and filtered, and the filtrate was concentrated to give 16 g of 4-difluoromethoxyphenol. NMR: TMS (CDCl3) 4.12 ppm (S) (1) 6.35 ppm (T) (1) 6.72 ppm (D) (2) 6.95 ppm (D) (2)
  • 4
  • O-ethyl S-propylthiophosphoryl chloride [ No CAS ]
  • [ 87789-47-7 ]
  • [ 88797-83-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; toluene; acetonitrile; EXAMPLE 1 Synthesis of O-ethyl S-propyl O-(4-difluoromethoxyphenyl)monothiophosphate 6.0 g of O-ethyl S-propylthiophosphoryl chloride were added gradually to 6.0 g of <strong>[87789-47-7]4-difluoromethoxyphenol</strong> and 5.1 g of potassium carbonate in 100 ml of acetonitrile, and stirring was continued for 3 hours at 50 C. and thereafter for 12 hours at room temperature. The solvent was removed in a rotary evaporator, 400 ml of toluene and 100 ml of water were added, the organic phase was washed with 2N sodium hydroxide solution and with water and dried over sodium sulfate, and the solvent and volatile impurities were removed at 40 C. and under 0.1 mbar. 6.5 g of an oil of refractive index nD21 =1.4920 were obtained as a residue.
  • 5
  • [ 87789-47-7 ]
  • [ 1134197-98-0 ]
YieldReaction ConditionsOperation in experiment
With nitric acid; In 1,2-dichloro-ethane; at 0℃; for 1.16667h; 4-(Difluoromethoxy)phenol (500 mg, 3.12 mmol) was dissolved in DCE (3 ml_). The reaction mixture was cooled to 0 0C and nitric acid (0.488 ml_, 10.92 mmol) was added dropwise over 10 min. The reaction mixture was stirred for a further hour at 0 C, then poured into an ice/water mix (5 g in 5 ml_). DCE (10 ml.) was added and the layers separated. The organic layer was dried (MgSO4) and evaporated to dryness to give a crude brown oil (550 mg). Material was carried forward without further purification, as no separation between products was found in TLC solvent systems used. (M - H)- = 204.1H NMR delta (CDCI3): 6.51 (1 H, t, J = 71.2 Hz), 7.18 (1 H, d, J = 7.2 Hz), 7.3 (1 H, dd, J = 9.2, 2.8 Hz), 7.91 (1 H, s), 10.45 (1 H, s).
  • 6
  • [ 87789-47-7 ]
  • [ 403-42-9 ]
  • [ 1126633-16-6 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; In dimethyl sulfoxide; at 100℃; 81 a) 1-[4-(4-difluoromethoxy-phenoxy)-phenyl]-ethanoneA solution of 666 muL (5.52 mmol) of 4-fluoroacetophenone and 883 mg (5.52 mmol) of <strong>[87789-47-7]4-(difluoromethoxy)phenol</strong> in 10 mL DMSO was combined with 1.91 g (13.78 mmol) of potassium carbonate and stirred overnight at 100 C. The reaction mixture was poured onto 250 mL semisaturated sodium chloride solution and extracted twice with tert-butylmethylether. The organic phase was dried and evaporated down. The residue was purified by chromatography (silica gel, petroleum ether/ethyl acetate).Yield: 89% of theoryC15H12F2O3 (278.25)Mass spectrum: [M+H]+=279
  • 7
  • [ 87789-47-7 ]
  • [ 1126633-17-7 ]
  • 8
  • [ 87789-47-7 ]
  • [ 1126632-93-6 ]
  • 9
  • [ 87789-47-7 ]
  • [ 1126631-64-8 ]
  • 10
  • [ 87789-47-7 ]
  • [ 88798-12-3 ]
YieldReaction ConditionsOperation in experiment
67% With bromine; In chloroform; at 0 - 20℃; A solution of Br2 (7.84 mL, 153 mmol) in CHCl3 (40 mL) was added dropwise at 0 C to a solution of 13 (24.5 g, 153 mmol) in CHCl3 (200 mL). After stirring for 1 h at room temperature, the reaction mixture was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (5/1) to give 14 (24.5 g, 67% yield) as an orange oil.
67% With N-Bromosuccinimide; acetic acid; at 15℃; for 1.0h; Into a 1000-mL round-bottom flask was placed acetic acid (500 mL), <strong>[87789-47-7]4-(difluoromethoxy)phenol</strong> (50 g, 312 mmol) and NBS (55.6 g, 312 mmol). The reaction mixture was stirred for 1 h at 15 C. The resulting mixture was then added slowly to 1000 mL of water/ice with stirring. The resulting solution was extracted with ethyl acetate (3*1000 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane/petroleum ether (30/70). The appropriate fractions were collected and concentrated under reduced pressure. This resulted in 50 g (67%) of 2-bromo-<strong>[87789-47-7]4-(difluoromethoxy)phenol</strong> as a light yellow oil.
67% With N-Bromosuccinimide; acetic acid; at 15℃; for 1.0h; Into a 1000-mL round-bottom flask, was placed acetic acid (500 mL), 4- (difluoromethoxy)phenol (50 g, 312 mmol), NBS (55.6 g, 312 mmol). The resulting solution was stirred for 1 h at 15oC. The reaction was then quenched by the addition of 1000 mL of water/ice. The resulting solution was extracted with 3x1000 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with dichloromethane/petroleum ether (30/70). The appropriate fractions were collected and concentrated under vacuum. This resulted in 50 g (67%) of 2-bromo-<strong>[87789-47-7]4-(difluoromethoxy)phenol</strong> as light yellow oil.
  • 11
  • [ 87789-47-7 ]
  • [ 1345731-94-3 ]
  • 12
  • [ 87789-47-7 ]
  • [ 1345731-96-5 ]
  • 13
  • [ 87789-47-7 ]
  • tert-butyl {(R)-2-[2-acetyl-4-(difluoromethoxy)phenoxy]-1-methylethyl}carbamate [ No CAS ]
  • 14
  • [ 87789-47-7 ]
  • [ 1345731-97-6 ]
  • 15
  • [ 87789-47-7 ]
  • [ 1345731-62-5 ]
  • 16
  • [ 87789-47-7 ]
  • tert-butyl trans-[1-benzyl-3-(hydroxymethyl)piperidin-4-yl]carbamate [ No CAS ]
  • tert-butyl trans-[1-benzyl-3-[4-(difluoromethoxy)phenoxy]methyl}piperidin-4-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In toluene; at 20℃; C) tert-butyl trans- [l-benzyl-3-{ [4- (difluoromethoxy) henoxy] methyl }piperidin-4-yl] carbamate; To a solution of tert-butyl trans- [ l-benzyl-3- (hydroxymethyl) piperidin-4-yl] carbamate (0.50 g) , 4- (difluoromethoxy) phenol (0.35 g) and ADDP (0.59 g) in toluene (10 ml) was added Bu3P (0.58 ml) at room temperature. The mixture was stirred at room temperature overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over Na2S04 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (0.47 g) .¾ NMR (300 MHz, CDC13). delta 1.40 (9H, s) , 1.46-1.54 (1H, m) , 1.90- 2.13 (4H, m), 2.85 (1H, d, J = 12.1 Hz), 3.16 (1H, d, J = 7.6 Hz), 3.36-3.52 (2H,. m) , 3.58 (1H, d, J = 13.2 Hz), 3.77 (1H, t, J = 7.9 Hz), 4.00 (1H, d, J = 7.2 Hz), 4.46 (1H, d, J = 7.9 Hz), 6.40 (1H, t, J = 74.4 Hz) ,. 6.82 (2H, d, J = 9.1 Hz), 7.03 (2H, d, J = 9.1 Hz), 7.21-7.38 (5H, m).
  • 17
  • [ 87789-47-7 ]
  • [ 1542205-91-3 ]
  • tert-butyl 3-[4-[4-(difluoromethoxy)phenoxy]phenyl]sulfonyl-3-(tetrahydropyran-2-yloxycarbamoyl)-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]
  • 18
  • [ 87789-47-7 ]
  • 2-chloro-N-(1-(3-(4-chlorophenoxy)propyl)piperidin-4-yl)acetamide [ No CAS ]
  • N-(1-(3-(4-chlorophenoxy)propyl)piperidin-4-yl)-2-(4-(difluoromethoxy)phenoxy)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66.9% With caesium carbonate; In acetonitrile; at 20 - 80℃; for 16.0h; To a stirred solution of 2-chloro-N-(1 -(3-(4-chlorophenoxy)propyl)piperidin-4- yl)acetamide (0.1 5 g, 0.43 mmol, 1 .0 equiv.) in acetonitrile (20 mL) was added caesium carbonate (0.35 g, 1 .08 mmol, 2.5 equiv.) and compound <strong>[87789-47-7]4-(difluoromethoxy)phenol</strong> (0.08 mL, 0.65 mmol, 1 .5 equiv.) at room temperature and then reaction mixture was stirred at 80 C for 16 h.. After consumption of the starting material (TLC, 5 % MeOH in DCM), reaction mixture was concentrated under reduced pressure and to the residue obtained was added water (5 mL), stirred for 15 - 20 mins and was filtered through sintered funnel. The solid obtained was washed with water (10 mL), diethyl ether (3 x 10 mL) and n- pentane (2 x 1 0 mL), dried under high vaccum to give N-(1 -(3-(4- chlorophenoxy)propyl)piperidin-4-yl)-2-(4-(difluoromethoxy)phenoxy)acetamide (0.1 36 g, 66.9 % yield) as off white solid. LCMS (ES) m/z = 469.1 [M+H]+. 1H NMR (400 MHz, DMSO-de) delta ppm 1 .42 - 1 .50 (m, 2 H), 1 .65 - 1 .68 (m, 2 H), 1 .82 (t, J = 6.6 Hz, 2 H), 1 .94 (t, J = 1 1 .0 Hz, 2 H), 2.37 (t, J = 6.8 Hz, 2 H), 2.77 - 2.80 (m, 2 H), 3.59 - 3.60 (m, 1 H), 3.97 (t, J = 6.2 Hz, 2 H), 4.43 (s, 2 H), 6.88 (s, 0.25 H), 6.92 - 6.97 (m, 4 H), 7.07 (s, 0.25 H), 7.10 (d, J = 8.8 Hz, 2 H), 7.25 (s, 0.25 H), 7.29 (d, J = 8.8 Hz, 2 H), 7.89 (d, J = 8.0 Hz, 1 H).
  • 19
  • 1-(benzyloxy)-4-(difluoromethoxy)benzene [ No CAS ]
  • [ 87789-47-7 ]
YieldReaction ConditionsOperation in experiment
78% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2327.23 Torr; Into a 3000-mL round-bottom flask was placed methanol (1500 mL), 1-(benzyloxy)-4-(difluoromethoxy)benzene (140 g, 559 mmol) and 10% Palladium carbon (15 g, 141 mmol). The resulting mixture was stirred under hydrogen (?45 psi) overnight at room temperature. The catalysts were filtered out. The filtrate was concentrated under reduced pressure. This reaction was repeated three times. This resulted in 300 g (78%) of 4-(difluoromethoxy)phenol as a yellow oil.
78% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 23.2723 Torr; Into a 3000-mL round-bottom flask, was placed methanol (1500 mL), 1-(benzyloxy)-4- (difluoromethoxy)benzene (140 g, 559 mmol), 10% Pd/C (15 g). The resulting mixture was stirred under hydrogen (~45 psi) overnight at room temperature. The catalysts were filtered off. The filtrate was concentrated under vacuum. This reaction was repeated three batches. This resulted in 300 g (78%) of 4-(difluoromethoxy)phenol as yellow oil.
  • 20
  • [ 87789-47-7 ]
  • 2-bromo-1,4-bis(difluoromethoxy)benzene [ No CAS ]
  • 21
  • [ 87789-47-7 ]
  • 5-[2,5-bis(difluoromethoxy)phenyl]-4-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazole [ No CAS ]
  • 22
  • [ 87789-47-7 ]
  • 5-[2,5-bis(difluoromethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-4-amine [ No CAS ]
  • 23
  • [ 87789-47-7 ]
  • N-[5-[2,5-bis(difluoromethoxy)phenyl]-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 24
  • [ 87789-47-7 ]
  • N-[3-[2,5-bis(difluoromethoxy)phenyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 25
  • [ 87789-47-7 ]
  • N-[3-[2,5-bis(difluoromethoxy)phenyl]-1-[(dimethylcarbamoyl)methyl]-1H-pyrazol-4-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide [ No CAS ]
  • 26
  • [ 103-16-2 ]
  • [ 87789-47-7 ]
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