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[ CAS No. 6783-05-7 ] {[proInfo.proName]}

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Chemical Structure| 6783-05-7
Chemical Structure| 6783-05-7
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Product Details of [ 6783-05-7 ]

CAS No. :6783-05-7 MDL No. :MFCD00963621
Formula : C8H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VKIJXFIYBAYHOE-VOTSOKGWSA-N
M.W : 147.97 Pubchem ID :5702628
Synonyms :

Calculated chemistry of [ 6783-05-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.67
TPSA : 40.46 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) : -6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 0.6
Log Po/w (MLOGP) : 0.85
Log Po/w (SILICOS-IT) : -0.29
Consensus Log Po/w : 0.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.64 mg/ml ; 0.0111 mol/l
Class : Very soluble
Log S (Ali) : -1.93
Solubility : 1.75 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.36
Solubility : 6.5 mg/ml ; 0.044 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 6783-05-7 ]

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 [ 6783-05-7 ]

* 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.

  • Upstream synthesis route of [ 6783-05-7 ]
  • Downstream synthetic route of [ 6783-05-7 ]

[ 6783-05-7 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 588-72-7 ]
  • [ 6783-05-7 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere
General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.
Reference: [1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
  • 2
  • [ 536-74-3 ]
  • [ 6783-05-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2803 - 2807
[2] Advanced Synthesis and Catalysis, 2003, vol. 345, # 12, p. 1273 - 1286
[3] Heterocycles, 2002, vol. 57, # 5, p. 871 - 879
[4] Journal of Organic Chemistry, 2008, vol. 73, # 5, p. 1898 - 1905
[5] Angewandte Chemie - International Edition, 2003, vol. 42, # 29, p. 3399 - 3404
[6] Organic Preparations and Procedures International, 2004, vol. 36, # 6, p. 573 - 579
[7] Synthesis, 2007, # 10, p. 1542 - 1546
[8] Organic Letters, 1999, vol. 1, # 10, p. 1683 - 1686
[9] Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 62 - 67
[10] Journal of Fluorine Chemistry, 2013, vol. 151, p. 58 - 62
[11] Organic Letters, 2017, vol. 19, # 19, p. 5344 - 5347
[12] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671
  • 3
  • [ 6783-04-6 ]
  • [ 6783-05-7 ]
YieldReaction ConditionsOperation in experiment
333 mg at 80℃; for 1 h; Inert atmosphere To   catecholborane (1.20 g, 10 mmol) in a flame-dried flask (under vacuum) under a nitrogen atmosphere, was added dropwise phenylethynyl (9 mmol) at 0 °C. After stirred at 70 °C for 4–5 h, the reaction mixture was added dropwise with   water (20 mL) at 0 °C, and was stirred at 80 °C for 1 h. The resultant precipitate was filtered, washed with water and recrystallized from hot water to afford white   crystals 333 mg, yield, 25percent. Mp: 164–167 °C. Lit. 162–164 °C [6a]. 1H NMR (300 MHz, CDCl3): δ 7.79 (d, J = 18.1 Hz, 1H), 7.67–7.58 (m, 2H), 7.46–7.31 (m, 3H), 6.36 (d, J = 18.1 Hz, 1H), 4.30 (s, 2H).
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 4285 - 4299
[2] Tetrahedron, 2001, vol. 57, # 52, p. 10335 - 10345
[3] Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 62 - 67
[4] Journal of Fluorine Chemistry, 2013, vol. 151, p. 58 - 62
  • 4
  • [ 83947-56-2 ]
  • [ 6783-05-7 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 19, p. 5344 - 5347
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671
  • 5
  • [ 201852-49-5 ]
  • [ 6783-05-7 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7364 - 7369
  • 6
  • [ 7732-18-5 ]
  • [ 536-74-3 ]
  • [ 274-07-7 ]
  • [ 6783-05-7 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 7, p. 1906 - 1909
  • 7
  • [ 536-74-3 ]
  • [ 274-07-7 ]
  • [ 6783-05-7 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 23, p. 5812 - 5815
  • 8
  • [ 13826-27-2 ]
  • [ 536-74-3 ]
  • [ 6783-05-7 ]
Reference: [1] Journal of Organometallic Chemistry, 1996, vol. 507, # 1-2, p. 207 - 214
  • 9
  • [ 6688-97-7 ]
  • [ 6783-05-7 ]
Reference: [1] Journal of Organometallic Chemistry, 1966, vol. 5, p. 506 - 519
[2] Journal of Organometallic Chemistry, 1966, vol. 5, p. 506 - 519
[3] , Gmelin Handbook: B: B-Verb.9, 5.2.6, page 205 - 215,
  • 10
  • [ 59278-44-3 ]
  • [ 100-52-7 ]
  • [ 6783-05-7 ]
Reference: [1] Journal of the American Chemical Society, 1975, vol. 97, # 19, p. 5608 - 5609
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