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[ CAS No. 867333-43-5 ] {[proInfo.proName]}

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Chemical Structure| 867333-43-5
Chemical Structure| 867333-43-5
Structure of 867333-43-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 867333-43-5 ]

CAS No. :867333-43-5 MDL No. :MFCD17015778
Formula : C8H8BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :IPDZHWUWADJUMR-UHFFFAOYSA-N
M.W : 160.97 Pubchem ID :53216743
Synonyms :

Calculated chemistry of [ 867333-43-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.95
TPSA : 64.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.91
Log Po/w (WLOGP) : -0.45
Log Po/w (MLOGP) : -0.03
Log Po/w (SILICOS-IT) : -0.32
Consensus Log Po/w : 0.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.72
Solubility : 3.1 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (Ali) : -1.84
Solubility : 2.3 mg/ml ; 0.0143 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.75
Solubility : 2.86 mg/ml ; 0.0178 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.96

Safety of [ 867333-43-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 867333-43-5 ]

* 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 [ 867333-43-5 ]
  • Downstream synthetic route of [ 867333-43-5 ]

[ 867333-43-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 121-43-7 ]
  • [ 42872-74-2 ]
  • [ 867333-43-5 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 20 h; Inert atmosphere
Step 1 : Synthesis of 5-cyano-2-methylphenylboronic acid First, 9.5 g (50 mmol) of 3-bromo-4-methylbenzonitrile was put into a 500 mL three-neck flask, and the atmosphere in the flask was replaced with nitrogen. Then, 250 mL of tetrahydrofuran (THF) was added, and the mixture was stirred at -78 °C for 30 minutes. Into this mixed solution, 34 mL (55 mmol) of a 1.63M hexane solution of -butyllithium (-BuLi) was dropped, followed by stirring at -78 °C for 1.5 hours. After that, 7.3 mL (65 mmol) of trimethyl borate was added to the mixture and this solution was stirred for 20 hours while the temperature was raised to room temperature. To this solution was added 100 mL of 1M hydrochloric acid and stirring was performed for 30 minutes. The obtained mixture was separated to an aqueous layer and an organic layer, and the aqueous layer was subjected to extraction with ethyl acetate. The organic layer and a solution of the extract were combined, and washed with saturated saline. Anhydrous magnesium sulfate was added to the obtained solution for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was washed with toluene and hexane, so that 4.3 g of a white solid was obtained in a yield of 53 percent. The obtained white solid was identified as 5-cyano-2-methylphenylboronic acid by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-10) below.
Reference: [1] Patent: WO2016/203350, 2016, A1, . Location in patent: Paragraph 1195
[2] Journal of the American Chemical Society, 2002, vol. 124, # 31, p. 9014 - 9015
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