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[ CAS No. 87199-15-3 ] {[proInfo.proName]}

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Chemical Structure| 87199-15-3
Chemical Structure| 87199-15-3
Structure of 87199-15-3 * Storage: {[proInfo.prStorage]}
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Product Citations

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon , et al. DOI:

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

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Product Details of [ 87199-15-3 ]

CAS No. :87199-15-3 MDL No. :MFCD01317846
Formula : C7H9BO3 Boiling Point : -
Linear Structure Formula :- InChI Key :HGTDLKXUWVKLQX-UHFFFAOYSA-N
M.W : 151.96 Pubchem ID :2734662
Synonyms :
3-Hydroxymethylbenzeneboronic acid
Chemical Name :3-(Hydroxymethyl)phenylboronic acid

Calculated chemistry of [ 87199-15-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 3.0
Molar Refractivity : 42.4
TPSA : 60.69 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) : -7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.06
Log Po/w (WLOGP) : -1.29
Log Po/w (MLOGP) : -0.27
Log Po/w (SILICOS-IT) : -0.91
Consensus Log Po/w : -0.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.02
Solubility : 14.6 mg/ml ; 0.0964 mol/l
Class : Very soluble
Log S (Ali) : -0.76
Solubility : 26.2 mg/ml ; 0.172 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.1
Solubility : 12.0 mg/ml ; 0.0793 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 87199-15-3 ]

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 [ 87199-15-3 ]

* 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 [ 87199-15-3 ]
  • Downstream synthetic route of [ 87199-15-3 ]

[ 87199-15-3 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 87199-15-3 ]
  • [ 1877-77-6 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
  • 2
  • [ 5419-55-6 ]
  • [ 103978-12-7 ]
  • [ 87199-15-3 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h;
Stage #2: at 20℃; for 2.83 h;
Example 3B: 3 -(Hydroxymethyl)phenylboronic acid j00214j Example 3A (150 mg, 0.49 8 mmol) was dissolved in THF (2.49 mL) and cooled to -78 °C. BuLi (431 .iL, 0.647 mmol) was and the reaction was stirred for 30 mm. After this time, triisopropyl borate (231 jiL, 0.996 mmol) was added and stirring continued for 20 mm, then the reaction was warmed to ambient temperature and allowed to stir for 2.5 h. The reaction mixture was diluted with EtOAc and washed with water,then brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was then dissolved in HPLC solvent B (90:10:0.1 MeCN:H20:TFA) and allowed to stir at ambient temperature for 1 h. The reaction was concentrated in vacuo and the crude material was purified by Prep LC (Axia Luna 5t C18 30x100 mm column, 10 mm gradient from 20 to 100percent B in A, A = 10:90:0.1 MeCN:H20:TFA, B = 90:10:0.1MeCN:H20:TFA) to yield Example 3B (57 mg, 75percent). 1H NMR (400 MHz, ACETONITRILE-d3) ö ppm 7.75 (1 H, s), 7.67 (1 H, d, J=7.28 Hz), 7.40 - 7.48 (1 H, m), 7.30 - 7.40 (1 H, m), 4.60 (2 H, s).
Reference: [1] Patent: WO2014/201073, 2014, A1, . Location in patent: Paragraph 00214
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72
  • 3
  • [ 109-72-8 ]
  • [ 121-43-7 ]
  • [ 15852-73-0 ]
  • [ 87199-15-3 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In tetrahydrofuran; hexane Part A
3-Bromobenzyl alcohol (2.0 g, 10.7 mmol) was dissolved in dry THF (50 ml) in a dry 100 ml flask flushed with nitrogen.
The mixture was chilled in a dry ice/acetone bath. n-Butyl lithium (11 ml of a 2.13M solution in hexane, 23.5 mmol) was added.
The reaction was warmed to room temperature for 1 hour, then cooled in an ice water bath.
Trimethyl borate (1.3 ml, 11.2 mmol) was added and the mixture was stirred at room temperature overnight, then treated with 2N aqueous HCl to pH 2, and stirred for 3 hours.
Brine (15 ml) was added, and the mixture was extracted with ethyl acetate (3*15 ml).
The organic materials were combined, dried (MgSO4) then concentrated under reduced pressure which gave of 3-hydroxymethylbenzeneboronic acid (98percent) as a clear oil.
Reference: [1] Patent: US5444050, 1995, A,
  • 4
  • [ 15852-73-0 ]
  • [ 87199-15-3 ]
Reference: [1] Patent: WO2014/201073, 2014, A1,
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72
  • 5
  • [ 5419-55-6 ]
  • [ 15852-73-0 ]
  • [ 87199-15-3 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 6, p. 741 - 746
  • 6
  • [ 87199-15-3 ]
  • [ 364794-80-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 7
  • [ 87199-15-3 ]
  • [ 883738-27-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
  • 8
  • [ 76-09-5 ]
  • [ 87199-15-3 ]
  • [ 443776-76-9 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 18, p. 4850 - 4853
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