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[ CAS No. 147460-41-1 ] {[proInfo.proName]}

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Chemical Structure| 147460-41-1
Chemical Structure| 147460-41-1
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Product Details of [ 147460-41-1 ]

CAS No. :147460-41-1 MDL No. :MFCD00040939
Formula : C6H4BrFO Boiling Point : -
Linear Structure Formula :- InChI Key :HUVAOAVBKOVPBZ-UHFFFAOYSA-N
M.W : 191.00 Pubchem ID :2724600
Synonyms :

Calculated chemistry of [ 147460-41-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.12
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) : -5.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 2.63
Log Po/w (WLOGP) : 2.71
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 2.48
Consensus Log Po/w : 2.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.128 mg/ml ; 0.000669 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.377 mg/ml ; 0.00197 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.211 mg/ml ; 0.00111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 147460-41-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 147460-41-1 ]

* 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.

  • Upstream synthesis route of [ 147460-41-1 ]
  • Downstream synthetic route of [ 147460-41-1 ]

[ 147460-41-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 147460-41-1 ]
  • [ 74-88-4 ]
  • [ 450-88-4 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; To a pre-cooled suspension of 2-bromo-5-fluorophenol (5 g, 26.18 mmol) and potassium carbonate (10.84 g, 78.54 mmol) in DMF (15 mL) at 0-5° C., was added methyl iodide (4.75 mL, 39.27 mmol) and the resulting reaction mixture was stirred at room temperature for 16 hours.
The reaction mixture was partitioned between water (20 mL) and EtOAc (50 mL).
The organic layer was separated and the aqueous layer was further extracted with EtOAc (3*50 mL).
The organic layers were combined, washed with saturated brine solution (20 mL) and dried over Na2SO4, filtered and concentrated in vacuo to afford 1-bromo-4-fluoro-2-methoxybenzene as a colourless liquid in 93percent yield, 5.00 g.
1H NMR (400 MHz, DMSO-d6): δ ppm 3.86 (s, 3H), 6.74-6.79 (m, 1H), 7.06 (dd, 1H), 7.57-7.65 (m, 1H).
Reference: [1] Patent: US2014/171435, 2014, A1, . Location in patent: Paragraph 0505; 0506
[2] Patent: EP1510516, 2005, A1, . Location in patent: Page/Page column 86-87
[3] Patent: US2005/267105, 2005, A1, . Location in patent: Page/Page column 67
[4] Patent: US2002/55631, 2002, A1,
[5] Patent: US2002/86887, 2002, A1,
[6] Patent: US5688808, 1997, A,
[7] Patent: US5688810, 1997, A,
[8] Patent: US5693647, 1997, A,
[9] Patent: US5696127, 1997, A,
[10] Patent: US5693646, 1997, A,
[11] Patent: US5696130, 1997, A,
[12] Patent: US5696133, 1997, A,
[13] Patent: WO2003/99787, 2003, A1, . Location in patent: Page 150
[14] Patent: EP1380576, 2004, A1, . Location in patent: Page 93
[15] Patent: US2007/111984, 2007, A1, . Location in patent: Page/Page column 32
[16] Patent: US2007/129379, 2007, A1, . Location in patent: Page/Page column 25
[17] Patent: WO2007/64316, 2007, A1, . Location in patent: Page/Page column 151-152
[18] Patent: WO2013/28474, 2013, A1, . Location in patent: Page/Page column 69; 72
[19] Patent: WO2014/99633, 2014, A2, . Location in patent: Page/Page column 64
[20] Patent: EP2744499, 2016, B1, . Location in patent: Paragraph 0166; 0168
  • 2
  • [ 77-78-1 ]
  • [ 147460-41-1 ]
  • [ 450-88-4 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone at 60℃; for 2 h; a) 2-Bromo-5-fluoroanisole To a suspension of 2-bromo-5-fluorophenol (20.0 g, 104.7 mmol) and potassium carbonate (21.71 g, 157.1 mmol) in acetone (200 mL) was added dimethyl sulphate (10. 90 ML, 115.2 mmol). The resulting suspension was allowed to stir at 60C for 2 h before being allowed to cool and then concentrated in vacuo. The residue was dissolved in ether (200 mL) and water (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 50 mL), saturated sodium bicarbonate solution (50 mL) with the resulting organic phase being dried (MGS04) and the solvent evaporated in vacuo to give a pale yellow oil (21.46 g, 100percent). ON (300 MHz, CDC13) 7.45 (1H, dd, Ar), 6.70-6. 55 (2H, m, Ar), 3. 90 (3H, s, OCH3)
100% With potassium carbonate In acetone at 60℃; for 2 h; 3-FLUORO-2-METHOXVBENZALDEHYDE To a suspension of 3-fluoro-2-hydroxybenzaldehyde (5.328 g, 38.02 mmol) and potassium carbonate (7.88 g, 57.03 mmol) in acetone (60 mL) was added dimethyl sulphate (3.96 ML, 41.83 mmol). The resulting suspension was stirred at 60C for 2 h before being allowed to cool and then concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL) and water (50 mL). The organic phase was washed with saturated sodium bicarbonate (50 mL) with the resulting organic phase being dried (MGS04) and the solvent evaporated in vacuo to give a pale yellow oil (6.262 g, 38.02 mmol, 100percent). OH (300 MHz, CDC13) 10.40 (1H, s, CHO), 7.60 (1H, d, Ar), 7.30 (1H, m, Ar), 7.10 (1H, m, Ar), 4.10 (3H, s, OCH3).
100% With potassium carbonate In acetone at 60℃; for 2 h; a) 2-Bromo-5-fluoroanisole To a suspension of 2-bromo-5-fluorophenol (20.0 g, 104.7 mmol) and potassium carbonate (21.71 g, 157.1 mmol) in acetone (200 mL) was added dimethyl sulphate (10.90 ML, 115.2 mmol). The resulting suspension was allowed to stir at 60C for 2 h before being allowed to cool and then concentrated in vacuo. The residue was dissolved in ether (200 mL) and water (100 mL). The organic phase was washed with aqueous hydrochloric acid (2 N, 50 mL), saturated sodium bicarbonate solution (50 ML) with the resulting organic phase being dried (MgSO4) and the solvent evaporated in vacuo to give a pale yellow oil (21.46 g, 100percent). SN (300 MHz, CDCl3) 7.45 (1H, dd, Ar), 6.70-6. 55 (2H, m, Ar), 3.90 (3H, s, OCH3).
Reference: [1] Patent: WO2004/43903, 2004, A1, . Location in patent: Page 29
[2] Patent: WO2004/43903, 2004, A1, . Location in patent: Page 30
[3] Patent: WO2004/43904, 2004, A1, . Location in patent: Page 28
  • 3
  • [ 348-57-2 ]
  • [ 121219-03-2 ]
  • [ 147460-41-1 ]
Reference: [1] Synlett, 2009, # 4, p. 633 - 637
  • 4
  • [ 450-88-4 ]
  • [ 147460-41-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 139 - 150
  • 5
  • [ 348-57-2 ]
  • [ 121219-03-2 ]
  • [ 147460-41-1 ]
Reference: [1] Synlett, 2009, # 4, p. 633 - 637
  • 6
  • [ 147460-41-1 ]
  • [ 253429-31-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 447 - 458
[2] Patent: WO2008/82484, 2008, A1,
[3] Patent: CN108658908, 2018, A,
  • 7
  • [ 2032-35-1 ]
  • [ 147460-41-1 ]
  • [ 253429-31-1 ]
Reference: [1] Synlett, 2004, # 8, p. 1351 - 1354
  • 8
  • [ 147460-41-1 ]
  • [ 191014-55-8 ]
Reference: [1] Patent: WO2013/28474, 2013, A1,
[2] Patent: EP2744499, 2016, B1,
  • 9
  • [ 1895-39-2 ]
  • [ 147460-41-1 ]
  • [ 954235-83-7 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 15 h; itermediteExthp1eI5. ‘sulfOnamide ‘,“a) .To a solutiOn of 2-brotho-5-fludrophenol (3g. 15.7 mmol) in DMF (5 ml) was added cesium carbonate (7.7 g, 23.56 mmol, 1.5 eq) and sodium chlorodifluoroacetate(6 g, 39.26 nimol;2:5 eq) and the reaction mixture was heated at 100°C for 15 h. Thereaction mixture was then exttacted with Water and ethyl acetate (3 x 50 mI) Thecombined Organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica ge110percent ethyl acetate in hexane) in 58 percent yield (2.2 g).
Reference: [1] Patent: WO2014/162039, 2014, A1, . Location in patent: Page/Page column 41
[2] Patent: EP2394987, 2011, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2012/143329, 2012, A1, . Location in patent: Page/Page column 121
  • 10
  • [ 147460-41-1 ]
  • [ 76-04-0 ]
  • [ 954235-83-7 ]
Reference: [1] Patent: EP3345906, 2018, A1, . Location in patent: Paragraph 0103; 0104
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