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[ CAS No. 4923-87-9 ] {[proInfo.proName]}

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Chemical Structure| 4923-87-9
Chemical Structure| 4923-87-9
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Product Details of [ 4923-87-9 ]

CAS No. :4923-87-9 MDL No. :MFCD03069318
Formula : C8H5BrS Boiling Point : -
Linear Structure Formula :- InChI Key :RDSIMGKJEYNNLF-UHFFFAOYSA-N
M.W : 213.09 Pubchem ID :2776578
Synonyms :

Calculated chemistry of [ 4923-87-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.53
TPSA : 28.24 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 3.78
Log Po/w (WLOGP) : 3.66
Log Po/w (MLOGP) : 3.38
Log Po/w (SILICOS-IT) : 4.37
Consensus Log Po/w : 3.52

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.21
Solubility : 0.0132 mg/ml ; 0.0000619 mol/l
Class : Moderately soluble
Log S (Ali) : -4.07
Solubility : 0.0183 mg/ml ; 0.0000858 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.2
Solubility : 0.0134 mg/ml ; 0.000063 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.89

Safety of [ 4923-87-9 ]

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 [ 4923-87-9 ]

* 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 [ 4923-87-9 ]
  • Downstream synthetic route of [ 4923-87-9 ]

[ 4923-87-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 4923-87-9 ]
  • [ 20532-28-9 ]
Reference: [1] Organometallics, 2018, vol. 37, # 18, p. 2941 - 2944
[2] Advanced Synthesis and Catalysis, 2013, vol. 355, # 4, p. 627 - 631
  • 2
  • [ 4923-87-9 ]
  • [ 19301-35-0 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 7, p. 1968 - 1972[3] Angew. Chem., 2018, vol. 130, p. 1986 - 1990,5
  • 3
  • [ 4923-87-9 ]
  • [ 20532-34-7 ]
Reference: [1] Patent: US2014/243349, 2014, A1,
  • 4
  • [ 4923-87-9 ]
  • [ 73183-34-3 ]
  • [ 501945-71-7 ]
YieldReaction ConditionsOperation in experiment
86% With potassium acetate In dimethyl sulfoxide at 20 - 80℃; for 3 h; Dissolve 5-bromo-benzo [b] thiophene (J. Mater. Chem., 10: 2069-2081,2000 ; 49 g, 7.0 mmol) in DMSO (40 mL). Add bis (pinacolato) diboron (7 mmol), PdCl2 (dppf)-CH2Cl2 (0.33 mmol), and KOAc (20 mmol). Flush the flask with N2, and then heat the reaction mixture to 80°C with stirring. Continue to heat the reaction mixture for 3 hours, and then cool to room temperature. Add water (66 mL) and extract the aqueous layer with EtOAc (3 x 66 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 0-5percent Et20/pentane) to give 1.56 g of the title compound (86percent).
64% With potassium acetate In dimethyl sulfoxide at 85℃; for 1.5 h; Step E: Bis(pinacolato)diboron (1.3 g, 5.12 mmol), dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane (0.1 g, 0.14 mmol) and potassium acetate (1.4 g, 14.26 mmol) were charged in a 100 ml 3 neck round-bottomed flask which had been dried with a heat gun under vacuum and cooled under nitrogen prior to use. The mixture was degassed with nitrogen three times. A solution of 5-bromothiophene (1.0 g, 4.69 mmol) in dimethyl sulfoxide (20 ml) was added, the mixture was degassed again three times and was stirred at 85° C. for 1.5 hours. After cooling to room temperature, the mixture was filtered through diatomaceous earth and rinsed with water and ethyl acetate. Additional water was added to the filtrate which was extracted with ethyl acetate three times. The combined organic extracts were washed with brine once and dried over sodium sulfate to give the desired material (0.8 g, 64percent, 100percent AUC GC) after chromatography (9:1 to 5:1 heptane/ethyl acetate): 1H NMR (300 MHz, CDCl3) δ 8.24 (s, 1H), 7.81 (d, J=8.1 Hz, 1H), 7.68 (dd, J=8.1, 0.6 Hz, 1H), 7.34 (d, J=5.4 Hz, 1H), 7.28 (dd, J=5.4, 0.6 Hz, 1H), 1.30 (s, 12H).
Reference: [1] Patent: WO2004/9086, 2004, A1, . Location in patent: Page/Page column 49
[2] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 104
[3] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[5] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[6] Patent: US2008/45539, 2008, A1, . Location in patent: Page/Page column 18
[7] Patent: JP2015/531758, 2015, A, . Location in patent: Paragraph 0046; 0102
[8] ChemMedChem, 2018, vol. 13, # 9, p. 957 - 967
  • 5
  • [ 4923-87-9 ]
  • [ 185990-03-8 ]
  • [ 501945-71-7 ]
Reference: [1] Chemical Science, 2015, vol. 6, # 5, p. 2943 - 2951
  • 6
  • [ 4923-87-9 ]
  • [ 501945-71-7 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 6, p. 1167 - 1174
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