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[ CAS No. 19064-24-5 ] {[proInfo.proName]}

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Chemical Structure| 19064-24-5
Chemical Structure| 19064-24-5
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Product Details of [ 19064-24-5 ]

CAS No. :19064-24-5 MDL No. :MFCD00192035
Formula : C6H3F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SSNCMIDZGFCTST-UHFFFAOYSA-N
M.W : 159.09 Pubchem ID :87922
Synonyms :

Calculated chemistry of [ 19064-24-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.18
TPSA : 45.82 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) : -5.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.13
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.71
Log Po/w (MLOGP) : 1.73
Log Po/w (SILICOS-IT) : 0.55
Consensus Log Po/w : 1.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.644 mg/ml ; 0.00405 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.462 mg/ml ; 0.0029 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.33
Solubility : 0.753 mg/ml ; 0.00473 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 19064-24-5 ]

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 [ 19064-24-5 ]

* 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 [ 19064-24-5 ]
  • Downstream synthetic route of [ 19064-24-5 ]

[ 19064-24-5 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 19064-24-5 ]
  • [ 385-01-3 ]
YieldReaction ConditionsOperation in experiment
61% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 18.5 h; A solution of potassium TERT-BUTOXIDE (1.23 g, 11 mmol) in 25 mL of anhydrous DMSO was stirred at room temperature for 30 minutes and treated with 1, 3-difluoro-2-nitrobenzene (1.59 g, 10 mmol). After 18 hours, the mixture was diluted with 150 mL of 1 N aqueous sulfuric acid and extracted with three 50 mL portions of diethyl ether. The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in 50 mL of trifluoroacetic acid. After 30 minutes at room temperature, the mixture was concentrated in vacuo, treated with 50 mL of 1 N aqueous sodium hydroxide, and extracted with three 30 mL portions of diethyl ether. The aqueous layer was acidified with 1 N aqueous sulfuric acid and extracted with two 50 mL portions of dichloromethane. The combined dichloromethane layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.3 g of 3-fluoro-2-nitrophenol as orange oil (61percent yield). An solution of 3-fluoro-2-nitrophenol (1.13 g, 7.2 mmol) and pyridine (0.65 mL, 8 mmol) in 15 mL of anhydrous dichloromethane was cooled in an ice bath and treated with a solution of triflic anhydride (1.33 mL, 7.9 mmol) in 3 mL of anhydrous dichloromethane. After 4 hours, the reaction mixture was diluted with 100 mL of dichloromethane, washed with two 30 mL portions of saturated aqueous sodium bicarbonate, two 30 mL portions of 1 N aqueous sulfuric acid, and two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in VACUA TAO give 2 g of the title product as a light brown oil (96percent yield).
Reference: [1] Patent: WO2005/30213, 2005, A1, . Location in patent: Page/Page column 182-183
[2] Magnetic Resonance in Chemistry, 1996, vol. 34, # 6, p. 440 - 446
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[4] Patent: WO2011/106986, 2011, A1,
[5] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[6] Patent: US2010/94000, 2010, A1, . Location in patent: Page/Page column 29
  • 2
  • [ 5509-65-9 ]
  • [ 19064-24-5 ]
YieldReaction ConditionsOperation in experiment
52% With sodium perborate In acetic acid at 80 - 90℃; for 1 h; Step 1:
A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80° C. 2,6-Difluoroaniline (11.0 g, 85 mmol) in glacial acetic acid (50 mL) was added slowly to the mixture.
The temperature was maintained between 80-90° C. for 1 hour.
The cooled reaction mixture was poured into water and extracted twice with diethyl ether.
The combined organic layers were washed with a dilute solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated.
The residue was purified via Biotage chromatography (FlasH90i, silica, 10percent THF/hexane) and the product washed with hexane to afford 2,6-difluoronitrobenzene (7.0 g) (52percent). MS (ESI) m/z 160 ([M+H]+).
52% With sodium perborate In acetic acid at 80 - 90℃; for 1 h; Step 1: A mixture of sodium perborate tetrahydrate (65 g, 422 mmol) in glacial acetic acid (250 mL) was stirred at 80° C. 2,6-Difluoroaniline (11.0 g, 85 mmol) in glacial acetic acid (50 mL) was added slowly to the mixture. The temperature was maintained between 80-90° C. for 1 hour. The cooled reaction mixture was poured into water and extracted twice with diethyl ether. The combined organic layers were washed with a dilute solution of sodium bicarbonate, dried over anhydrous magnesium sulfate and evaporated. The residue was purified via Biotage chromatography (FlasH90i, silica, 10percent THF/hexane) and the product washed with hexane to afford 2,6-difluoronitrobenzene (7.0 g) (52percent). MS (ESI) m/z 160 ([M+H]+).
Reference: [1] Patent: US2005/222148, 2005, A1, . Location in patent: Page/Page column 58
[2] Patent: US2008/153873, 2008, A1, . Location in patent: Page/Page column 20
[3] Journal of Organic Chemistry, 1992, vol. 57, # 21, p. 5577 - 5585
[4] European Journal of Organic Chemistry, 2006, # 5, p. 1109 - 1112
[5] Patent: US2006/9509, 2006, A1, . Location in patent: Page/Page column 8
  • 3
  • [ 98-95-3 ]
  • [ 402-67-5 ]
  • [ 19064-24-5 ]
  • [ 350-46-9 ]
  • [ 1493-27-2 ]
Reference: [1] Journal of Fluorine Chemistry, 1981, vol. 18, p. 363 - 374
[2] Journal of Fluorine Chemistry, 1981, vol. 18, p. 363 - 374
[3] Journal of Fluorine Chemistry, 1981, vol. 18, p. 363 - 374
  • 4
  • [ 5509-65-9 ]
  • [ 74087-85-7 ]
  • [ 19064-24-5 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 24, p. 5783 - 5788
  • 5
  • [ 29270-54-0 ]
  • [ 19064-24-5 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 5, p. 1109 - 1112
  • 6
  • [ 133117-48-3 ]
  • [ 372-18-9 ]
  • [ 19064-24-5 ]
  • [ 446-35-5 ]
Reference: [1] Journal of Fluorine Chemistry, 1998, vol. 92, # 1, p. 27 - 32
  • 7
  • [ 98-95-3 ]
  • [ 402-67-5 ]
  • [ 19064-24-5 ]
  • [ 446-35-5 ]
  • [ 2265-94-3 ]
  • [ 350-46-9 ]
  • [ 1493-27-2 ]
Reference: [1] Journal of Fluorine Chemistry, 1981, vol. 18, p. 363 - 374
  • 8
  • [ 133117-48-3 ]
  • [ 372-18-9 ]
  • [ 19064-24-5 ]
  • [ 446-35-5 ]
Reference: [1] Journal of Fluorine Chemistry, 1998, vol. 92, # 1, p. 27 - 32
  • 9
  • [ 98-95-3 ]
  • [ 402-67-5 ]
  • [ 19064-24-5 ]
  • [ 446-35-5 ]
  • [ 2265-94-3 ]
  • [ 350-46-9 ]
  • [ 1493-27-2 ]
Reference: [1] Journal of Fluorine Chemistry, 1981, vol. 18, p. 363 - 374
  • 10
  • [ 19064-24-5 ]
  • [ 18645-88-0 ]
Reference: [1] Patent: WO2013/34758, 2013, A1,
[2] Patent: WO2013/34755, 2013, A1,
  • 11
  • [ 67-56-1 ]
  • [ 19064-24-5 ]
  • [ 641-49-6 ]
YieldReaction ConditionsOperation in experiment
95% for 3 h; Heating / reflux To a solution of 2,6-difluoronitrobenzene (5 g, 32 mmol) in methanol (50 mL) was added potassium hydroxide (1.8 g, 32.5 mmol), and the mixture was heated to reflux for 3 hr. Water was added, and the mixture was extracted with dichloromethane. The organic layer was separated, dried, filtered, and evaporated to yield 5.1 g (95percent) of 1-fluoro-3-methoxy-2-nitrobenzene, 1e. MS m/z (MH+) 172.
Reference: [1] Patent: US2006/135763, 2006, A1, . Location in patent: Page/Page column 32-33
[2] Patent: US2009/93459, 2009, A1, . Location in patent: Page/Page column 29
  • 12
  • [ 19064-24-5 ]
  • [ 124-41-4 ]
  • [ 641-49-6 ]
Reference: [1] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[3] Patent: WO2011/106986, 2011, A1, . Location in patent: Page/Page column 119
  • 13
  • [ 19064-24-5 ]
  • [ 53981-23-0 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 7, p. 623 - 634
[2] Patent: US2003/162772, 2003, A1,
[3] Patent: WO2011/106986, 2011, A1,
[4] ChemMedChem, 2017, vol. 12, # 17, p. 1436 - 1448
  • 14
  • [ 19064-24-5 ]
  • [ 872141-25-8 ]
Reference: [1] Patent: US2011/59954, 2011, A1,
  • 15
  • [ 19064-24-5 ]
  • [ 932373-92-7 ]
Reference: [1] Patent: WO2008/119720, 2008, A1,
[2] Patent: WO2007/107567, 2007, A1,
  • 16
  • [ 19064-24-5 ]
  • [ 886762-75-0 ]
Reference: [1] Patent: WO2012/83170, 2012, A1,
[2] Patent: WO2013/26914, 2013, A1,
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