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[ CAS No. 54008-77-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 54008-77-4
Chemical Structure| 54008-77-4
Chemical Structure| 54008-77-4
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Product Details of [ 54008-77-4 ]

CAS No. :54008-77-4 MDL No. :MFCD02681987
Formula : C8H5BrO Boiling Point : -
Linear Structure Formula :- InChI Key :RNEOFIVNTNLSEH-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :2776264
Synonyms :

Calculated chemistry of [ 54008-77-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.91
TPSA : 13.14 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 3.57
Log Po/w (WLOGP) : 3.2
Log Po/w (MLOGP) : 2.31
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0208 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (Ali) : -3.53
Solubility : 0.0579 mg/ml ; 0.000294 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0142 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.47

Safety of [ 54008-77-4 ]

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 [ 54008-77-4 ]

* 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 [ 54008-77-4 ]
  • Downstream synthetic route of [ 54008-77-4 ]

[ 54008-77-4 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 91703-34-3 ]
  • [ 54008-77-4 ]
YieldReaction ConditionsOperation in experiment
92% With potassium phosphate; copper(l) iodide In tetrahydrofuran at 80℃; for 12 h; Inert atmosphere 2-bromobenzofuran. To a solution of 2-(2,2-dibromovinyl)phenol (2.8 g, 10 mmol) in tetrahydrofuran (30 mL) was added copper(I) iodide (0.1 g, 0.5 mmol) and potassium phosphate (4.2 g, 20 mmol). The reaction mixture was stirred at 80°C under nitrogen atmosphere for 12 hours. After the reaction, the mixture was poured into water (200 mL) and the mixture was extracted with ethyl acetate (200 mL). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether = 1 :20) to give the pure product 2- bromobenzofuran (1.8 g, 92percent).
92% With potassium phosphate; copper(l) iodide In tetrahydrofuran at 80℃; for 12 h; Inert atmosphere To a solution of 2-(2,2-dibromovinyl)phenol (2.8 g, 10 mmol) in tetrahydrofuran (30 mL) was added copper (I) iodide (0.1 g, 0.5 mmol) and potassium phosphate (4.2 g, 20 mmol). The reaction mixture was stirred at 80° C. under nitrogen atmosphere for 12 hours. After the reaction, the mixture was poured into water (200 mL) and the mixture was extracted with ethyl acetate (200 mL). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product 2-bromobenzofuran (1.8 g, 92percent).
Reference: [1] Tetrahedron, 2011, vol. 67, # 33, p. 5913 - 5919
[2] Chemical Communications, 2011, vol. 47, # 37, p. 10476 - 10478
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4095 - 4101
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 21, p. 4172 - 4178
[5] Chemistry - A European Journal, 2015, vol. 21, # 4, p. 1482 - 1487
[6] Chemical Communications, 2009, # 35, p. 5236 - 5238
[7] Advanced Synthesis and Catalysis, 2012, vol. 354, # 8, p. 1585 - 1592
[8] Patent: WO2013/75083, 2013, A1, . Location in patent: Paragraph 00335; 00337
[9] Patent: US9206128, 2015, B2, . Location in patent: Page/Page column 166; 168
[10] European Journal of Organic Chemistry, 2013, # 4, p. 781 - 788
[11] Organic and Biomolecular Chemistry, 2013, vol. 11, # 3, p. 420 - 424
  • 2
  • [ 1378942-55-2 ]
  • [ 54008-77-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 21, p. 4172 - 4178
  • 3
  • [ 91703-34-3 ]
  • [ 54008-77-4 ]
  • [ 41014-29-3 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 4, p. 781 - 788
  • 4
  • [ 603-33-8 ]
  • [ 91703-34-3 ]
  • [ 54008-77-4 ]
  • [ 1839-72-1 ]
  • [ 92-52-4 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 4, p. 781 - 788
  • 5
  • [ 90-02-8 ]
  • [ 54008-77-4 ]
Reference: [1] Patent: WO2013/75083, 2013, A1,
[2] Chemistry - A European Journal, 2015, vol. 21, # 4, p. 1482 - 1487
[3] Patent: US9206128, 2015, B2,
  • 6
  • [ 496-41-3 ]
  • [ 54008-77-4 ]
  • [ 64150-61-4 ]
Reference: [1] Chemical Science, 2018, vol. 9, # 15, p. 3860 - 3865
  • 7
  • [ 1378942-55-2 ]
  • [ 54008-77-4 ]
  • [ 1394285-87-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 8, p. 1585 - 1592
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