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[ CAS No. 858855-11-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 858855-11-5
Chemical Structure| 858855-11-5
Chemical Structure| 858855-11-5
Structure of 858855-11-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 858855-11-5 ]

CAS No. :858855-11-5 MDL No. :MFCD16999931
Formula : C6H4BrIO Boiling Point : -
Linear Structure Formula :- InChI Key :KGVIGGKRRGGQMM-UHFFFAOYSA-N
M.W : 298.90 Pubchem ID :69399669
Synonyms :

Calculated chemistry of [ 858855-11-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.88
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 2.91
Log Po/w (WLOGP) : 2.76
Log Po/w (MLOGP) : 3.15
Log Po/w (SILICOS-IT) : 3.03
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.02
Solubility : 0.0286 mg/ml ; 0.0000955 mol/l
Class : Moderately soluble
Log S (Ali) : -3.0
Solubility : 0.302 mg/ml ; 0.00101 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0727 mg/ml ; 0.000243 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.19

Safety of [ 858855-11-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 858855-11-5 ]

* 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 [ 858855-11-5 ]
  • Downstream synthetic route of [ 858855-11-5 ]

[ 858855-11-5 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 858855-11-5 ]
  • [ 292638-85-8 ]
  • [ 19063-56-0 ]
Reference: [1] Heterocyclic Communications, 2010, vol. 16, # 2-3, p. 113 - 120
  • 2
  • [ 38191-34-3 ]
  • [ 858855-11-5 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With boron trifluoride diethyl etherate In tetrahydrofuran at -40 - -30℃; for 0.166667 h; Inert atmosphere
Stage #2: With tert.-butylnitrite In tetrahydrofuran at -30 - 20℃; for 1.5 h; Inert atmosphere
Stage #3: With iodine; potassium iodide In acetonitrile at 20℃; for 4 h; Inert atmosphere
To a solution of 1 (2.50 g, 13.30 mmol) in dry THF (12 mL) at -30 to -40 °C in a dry ice- MeCN bath was added boron trifluoride diethyl etherate (BF3 Et20, 4.92 mL, 39.90 mmol) dropwise under N2. After the mixture was stirred at -30 °C for 10 min, lBuONO (2.39 mL, 19.94 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 1.5 h to give a suspension. Petroleum ether (50 mL) was added to give more precipitate. The supernatant was removed by decantation and the solid left was washed with petroleum ether to afford a white solid. This solid was dissolved in dry MeCN (20 mL) and cooled in an ice bath. KI (11.00 g, 66.26 mmol) and I2 (6.00 g, 23.64 mmol) were added. The reaction mixture was stirred at room temperature for 4 h before saturated Na2S203 solution (50 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate three times. The combined organic extracts were washed with water followed by brine, dried over anhydrous Na2S04, and filtered through a pad of Celite. The solvent was removed and the resultant residue was purified by silica gel column chromatography using a mixture of ethyl acetate and petroleum ether (v/v 1 :9) as eluent to give 2 as a pale solid (2.83 g, 71percent); 1H NMR (CDC13) δ 7.50 (d, J= 8.5 Hz, 1H), 7.16 (d, J= 2.2 Hz, 1H), 6.84 (dd, J = 2.2, 8.5 Hz, 1H), 5.39 (s, 1H) ppm.
Reference: [1] Patent: WO2015/23355, 2015, A1, . Location in patent: Page/Page column 162
[2] Journal of the Chemical Society, 1934, p. 137
  • 3
  • [ 591-20-8 ]
  • [ 858855-11-5 ]
YieldReaction ConditionsOperation in experiment
47% With potassium iodate; sulfuric acid; potassium iodide In water at 20℃; for 18 h; KI (3.32 g, 20 mmol) and KIO3 (1.86 g, 8.7 mmol) were added to a stirred suspension of 3-bromophenol (5.00 g, 28.9 mmol) in a mixed solvent of H2O (120 mL) and H2SO4 (3 mL),and the mixture was stirred at r.t. After 18 h, the reaction was quenched with Na2S2O4 aq. and filtrated with Celite. The solution was extracted with EtOAc, and the organic layer was washed with brine and NaHCO3 aq., dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel(hexane) and preparative SEC using CHCl3 as the eluent, to give 2 as a white solid (4.08 g,47percent).
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2800 - 2808
  • 4
  • [ 791642-68-7 ]
  • [ 858855-11-5 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 8, p. 4824 - 4830
  • 5
  • [ 858855-11-5 ]
  • [ 74-88-4 ]
  • [ 791642-68-7 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In acetone at 20℃; for 12 h; To a solution of 5-bromo-2-iodo-phenol (1.00 g, 3.35 mmol) in acetone (10.0 mL) was added iodomethane (951 mg, 6.70 mmol) and anhydrous potassium carbonate (926 mg, 6.70 mmol) at it. The reaction mixture was stirred at it for 12 hrs. On completion, the reaction mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether) to give the title compound (1.00 g, 96percent yield). MR (400MHz, CDC13) δ = 7.61 (d, J =8.4 Hz, 1H), 6.95 (d, J =1.8 Hz, 1H), 6.87 (dd, J =8.4 Hz, 1.8 Hz, 1H), 3.89 (s, 3H).
Reference: [1] Patent: WO2017/156165, 2017, A1, . Location in patent: Paragraph 00704; 00705
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