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[ CAS No. 52189-63-6 ] {[proInfo.proName]}

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Chemical Structure| 52189-63-6
Chemical Structure| 52189-63-6
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Product Details of [ 52189-63-6 ]

CAS No. :52189-63-6 MDL No. :MFCD00012445
Formula : C8H9FO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IWFKMNAEFPEIOY-UHFFFAOYSA-N
M.W : 156.15 Pubchem ID :2774257
Synonyms :

Calculated chemistry of [ 52189-63-6 ]

Physicochemical Properties

Num. heavy atoms : 11
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 : 39.38
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) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 2.1
Log Po/w (WLOGP) : 2.26
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.4
Solubility : 0.618 mg/ml ; 0.00396 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 1.19 mg/ml ; 0.00762 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.189 mg/ml ; 0.00121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 52189-63-6 ]

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 [ 52189-63-6 ]

* 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 [ 52189-63-6 ]
  • Downstream synthetic route of [ 52189-63-6 ]

[ 52189-63-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 78-82-0 ]
  • [ 52189-63-6 ]
  • [ 22972-63-0 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 4, p. 712 - 713
  • 2
  • [ 10272-07-8 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
[2] Patent: WO2011/17125, 2011, A1, . Location in patent: Page/Page column 109
  • 3
  • [ 20469-65-2 ]
  • [ 52189-63-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 12, p. 2219 - 2222
  • 4
  • [ 17275-82-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 5
  • [ 99-10-5 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 6
  • [ 17213-58-0 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 7
  • [ 75996-26-8 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 8
  • [ 51707-38-1 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 9
  • [ 1132-21-4 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 10
  • [ 17213-57-9 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 11
  • [ 54132-76-2 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 12
  • [ 72470-95-2 ]
  • [ 52189-63-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
  • 13
  • [ 52189-63-6 ]
  • [ 75996-29-1 ]
YieldReaction ConditionsOperation in experiment
97% With boron tribromide In dichloromethane at -30 - 25℃; [00154] A solution of dimethoxy fluorobenzene (1) (10 g, 64 mmol ) in dry dichloromethane (40 mL) was cooled to -30 °C. To the cooled solution was added a solution of BBr3 (35.93 mL, 384 mmol ) in 60 mL of DCM slowly (in drops) over 30 min. After completion of addition, the reaction mixture was allowed to reach 25 °C and stirred for 12 h. After completion of reaction (by TLC using 30percent ethyl acetate and pet ether as eluting solvent), reaction mixture was cooled to 0 °C and then slowly quenched with water and stirred for 30 min at 25 °C. The reaction mixture was extracted with dichloromethane (3 x 100 mL) and the combined organic layer was washed with sodium bicarbonate, dried over Na2S04 and concentrated to get the product (2) as light brown solid. Yield: 8g (97percent)
97% With boron tribromide In dichloromethaneCooling with acetone-dry ice [0321} Preparation of 5-fluorobenzene- 1 ,3-diol: To a solution of 1 -fluoro-3 ,5-dimethoxybenzene (2.0 g, 12.8 mmol) in dichloromethane (50 mL) cooled in a dry ice/acetone bath was added a solution of boron tribromide (2.8 mL, 29.0 mmol) in dichloromethane (50 mL) dropwise over half an hour. The reaction mixture was stirred over night during which reaction temperature raised to room temperature, and then cooled in a ice/water bath. 60 mL of methanol was added slowly.Organic solvents were evaporated under vaccum. The residue was extracted between ethyl acetate and aqueous sodium bicarbonate. The ethyl acetate phase was dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography with 0-40percent ethyl acetate in hexanes to give desired product (1.6 g, 97percent yield) LC-MS: 127 (M-H).
93% With boron tribromide In dichloromethane at -30℃; for 2 h; To a -30° C. solution of 1-fluoro-3,5-dimethoxybenzene (1.56 g, 10 mmol) in 10 mL of CH2Cl2 was added 10 mL of BBr3/CH2Cl2 at while the solution was stirring.
The reaction mixture was stirred at -30° C. for 2 h and then allowed to warm up to RT overnight.
To the reaction mixture was added water and the product was extracted with EtOAc (3*10 mL).
The organic layers were washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, then the combined organic layers were concentrated under reduced pressure to afford a crude product.
The residue was purified by flash chromatography (1:1 EtOAc/hexanes) to give 5-fluorobenzene-1,3-diol as a yellow solid (1.2 g, 93percent). MS (ES+) C6H5FO2 requires: 128. found: 129 [M+H]+.
Reference: [1] Patent: WO2013/90921, 2013, A1, . Location in patent: Paragraph 00154
[2] Patent: WO2014/153000, 2014, A1, . Location in patent: Paragraph 0321
[3] Patent: US2016/60260, 2016, A1, . Location in patent: Paragraph 0237
[4] Journal of Organic Chemistry, 1997, vol. 62, # 19, p. 6469 - 6475
[5] Journal of Materials Chemistry, 2002, vol. 12, # 5, p. 1316 - 1324
[6] Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9719 - 9721
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1658 - 1666
[8] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1504 - 1507
[9] Patent: US6162931, 2000, A,
[10] Patent: WO2013/177668, 2013, A1, . Location in patent: Page/Page column 55-56
[11] Patent: WO2014/5217, 2014, A1, . Location in patent: Page/Page column 24; 25
[12] Patent: WO2014/29007, 2014, A1, . Location in patent: Paragraph 22; 23; 24
  • 14
  • [ 52189-63-6 ]
  • [ 850793-25-8 ]
YieldReaction ConditionsOperation in experiment
67% With boron tribromide In dichloromethane at -15 - 20℃; for 1.66 h; EXAMPLE 50; 3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methoxy]-2-chloro-3-fluorophenoxy}-5-chlorobenzonitrile; Step 1: 3-fluoro-5-methoxyphenol (50-1); Under nitrogen atmosphere, 1-fluoro-3,5-dimethoxybenzene (25 g, 160 mmol) was diluted in CH2Cl2 (200 mL, 0.8M) and then cooled to -15° C. Next, BBr3 (176 mL, 176 mmol, 1M in CH2Cl2) was slowly added to the reaction mixture. The reaction mixture was stirred at -15° C. for one and a half hours and at room temperature for 10 minutes. The reaction mixture was then cooled to 0° C. and slowly quenched with water (150 mL). The aqueous layer was then extracted with methylene chloride (3.x.100 mL). The organic extracts were dried over sodium sulfate and concentrated. Silica gel chromatography (1percent-30percent EtOAc/Hexanes) gave the mono demethylated product (50-1) (15 g, 67percent).
54%
Stage #1: With boron tribromide In dichloromethane at 0 - 20℃; for 22 h;
Stage #2: With ammonia In dichloromethane; water at 20℃; for 1.5 h;
Boron tribromide (1 M in dichloromethane, 9mL, 89.985mmol) was added drop wise to an ice- cooled solution of 3,5-dimethoxy fluorobenzene (3ml, 22,496mmol) in dichloromethane (2OmL) and the mixture was stirred at O0C to room temperature for 4 hours. The solution was cooled to O0C, further boron tribromide (4ml, 44.992mmol) was added and stirring continued, warming to room temperature for an additional 18 hours. The reaction was quenched with 0.88 ammonia solution and stirred at room temperature for 90 minutes. The organic layer was separated and extracted with 2N sodium hydroxide (30ml), which was then acidified to pH1 by drop wise addition of concentrated hydrochloric acid. The aqueous layer was then re- extracted with dichloromethane (3x15mL), the combined organic solution was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 54percent yield, 1.72g. 1HNMR(400MHz, CD3OD) δ: 3.72(s, 3H), 6.07-6.15(m, 3H)
53% With boron tribromide In dichloromethane at -78 - 0℃; Example 53
3- {4- [3-Fluoro-5- (2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-2-methyl-phenyl}- propionic acid Step A 3-Fluoro-5-methoxy-phenol A-78 °C solution of l-fluoro-3, 5-dimethoxybenzene (4. 98 g, 31.9 mmol) in dry CH2C12 (50 mL) is treated with a 1 M CH2C12 solution of boron tribromide (128 mL, 128 mmol), and the mixture is warmed to 0 °C and stirred under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 2.40 g (53percent) of the title compound. Rf= 0.49 (1/1 hexanes/EtOAc).'H NMR (400 MHz, CDCl3). MS (ES-) m/z mass calculated for C7H702F 142, found 141 (M-1,100percent).
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7163 - 7169
[2] Patent: US2007/21442, 2007, A1, . Location in patent: Page/Page column 57-58
[3] Patent: WO2007/34325, 2007, A1, . Location in patent: Page/Page column 48
[4] Patent: WO2005/37763, 2005, A1, . Location in patent: Page/Page column 94-95
[5] Patent: US2015/191473, 2015, A1, . Location in patent: Paragraph 0173
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