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[ CAS No. 158429-38-0 ] {[proInfo.proName]}

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Chemical Structure| 158429-38-0
Chemical Structure| 158429-38-0
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Product Details of [ 158429-38-0 ]

CAS No. :158429-38-0 MDL No. :MFCD16036117
Formula : C9H11BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :MOBGLFACQCDFEQ-UHFFFAOYSA-N
M.W : 193.99 Pubchem ID :22171419
Synonyms :

Calculated chemistry of [ 158429-38-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.51
TPSA : 66.76 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 : No
Log Kp (skin permeation) : -6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.04
Log Po/w (WLOGP) : -0.54
Log Po/w (MLOGP) : 0.52
Log Po/w (SILICOS-IT) : -0.39
Consensus Log Po/w : 0.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.82
Solubility : 2.96 mg/ml ; 0.0152 mol/l
Class : Very soluble
Log S (Ali) : -2.03
Solubility : 1.8 mg/ml ; 0.00928 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.75
Solubility : 3.41 mg/ml ; 0.0176 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 158429-38-0 ]

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 [ 158429-38-0 ]

* 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 [ 158429-38-0 ]
  • Downstream synthetic route of [ 158429-38-0 ]

[ 158429-38-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 5471-81-8 ]
  • [ 158429-38-0 ]
YieldReaction ConditionsOperation in experiment
91%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at -25 - -10℃; for 1.41667 h;
Stage #2: With Trimethyl borate In tetrahydrofuran at -20 - 0℃; for 1.05 h;
Stage #3: With phosphoric acid; water In tetrahydrofuran at -20 - 20℃;
Boronic Acid 9; A 3 -Liter round bottom flask equipped with a mechanical stirrer, thermocouple, and addition funnel was charged with 100 g of solid 4-iodo-3-methylbenzoic acid methyl ester and 1.0 L of dry THF. The mixture was cooled to -25 °C, and 218 mL of i-PrMgCl (2M in THF) was added dropwise over 25 min while the internal temperature was maintained at <-15 0C. The batch was kept at <-10 °C for 1 hr after the addition of the Grignard reagent. Analysis of a hydrolyzed aliquot showed greater than 97percent deiodination.The batch was then cooled to about -20 °C and quenched with trimethyl borate(77 g). The trimethyl borate reaction is exothermic. The temperature increased to about -4 °C during the addition of the trimethyl borate over 3 min. The resulting solution was aged for 1 h at <0 °C. The batch was then recooled to about -20 °C and further quenched with 1.0 L of IMH3PO4. This quench was also exothermic, raising the temperature to 3 °C by the end of the quench. The batch was aged at room temperature overnight.The THF was then removed by distillation at < 45 °C at reduced pressure. The product slurry was allowed to cool to room temperature, and then was filtered. The cake was washed with water (3 X 500 ml) and toluene (2 X 250 mL) and dried under vacuum with nitrogen sweep for 18 h to give the boronic acid 9 (64.3 g, 91percent) as an off-white crystalline solid.
Reference: [1] Patent: WO2008/82567, 2008, A1, . Location in patent: Page/Page column 6
[2] Patent: WO2007/79186, 2007, A2, . Location in patent: Page/Page column 63; 64
  • 2
  • [ 67-56-1 ]
  • [ 158429-66-4 ]
  • [ 158429-38-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3909 - 3913[2] Angew. Chem., 2016, p. 3977 - 3981,5
[3] Chemistry - A European Journal, 2004, vol. 10, # 1, p. 92 - 100
  • 3
  • [ 473596-87-1 ]
  • [ 158429-38-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1925 - 1944
  • 4
  • [ 7697-28-1 ]
  • [ 158429-38-0 ]
Reference: [1] Chemistry - A European Journal, 2004, vol. 10, # 1, p. 92 - 100
  • 5
  • [ 631-61-8 ]
  • [ 148547-19-7 ]
  • [ 73183-34-3 ]
  • [ 158429-38-0 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 87, p. 13261 - 13264
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