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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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Quality Control of [ 87199-15-3 ]

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Product Citations

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

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; 128796-39-4 ; ; ;

Product Details of [ 87199-15-3 ]

CAS No. :87199-15-3 MDL No. :MFCD01317846
Formula : C7H9BO3 Boiling Point : -
Linear Structure Formula :OHCH2C6H4B(OH)2 InChI Key :HGTDLKXUWVKLQX-UHFFFAOYSA-N
M.W : 151.96 Pubchem ID :2734662
Synonyms :
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 ?2

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.

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

[ 87199-15-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 87199-15-3 ]
  • [ 342777-09-7 ]
  • [ 939-57-1 ]
  • (E)-3-[2-(3-Hydroxymethyl-benzyl)-phenyl]-acrylic acid [ No CAS ]
  • 2
  • [ 104-21-2 ]
  • [ 87199-15-3 ]
  • {3-(4-methoxybenzyl)phenyl}methanol [ No CAS ]
  • 3
  • [ 108-86-1 ]
  • [ 87199-15-3 ]
  • [ 69605-90-9 ]
YieldReaction ConditionsOperation in experiment
89% With C44H32Cl4I2N4P2Pd2; tetrabutylammomium bromide; caesium carbonate; In water; at 100℃; for 12h;Inert atmosphere; General procedure: A Schlenk tube was charged with the prescribed amount of catalyst, aryl halide (1.0 mmol), 3-(hydroxymethyl)phenylboronicacid (1.5 mmol), TBAB (1.0 mmol), the selected base (3.0 mmol), and water under nitrogen atmosphere. The reaction mixture was heated at 100 C for 12 h. After cooling,the mixture was extracted with CH2Cl2, the solvent was evaporated,and the product was separated by passing through a silica gel column with CH2Cl2/ethyl acetate (5:1) aseluent. The products 2f, 2j, 2l, and 2o were new compounds and were determined by 1H and C13 NMR. Other products were characterized by comparison with data in the literature.
  • 5
  • [ 76-09-5 ]
  • [ 87199-15-3 ]
  • [ 443776-76-9 ]
  • 6
  • [ 87199-15-3 ]
  • [ 364794-80-9 ]
  • 7
  • [ 878207-92-2 ]
  • [ 87199-15-3 ]
  • methyl 6-[3-(hydroxymethyl)phenyl]-3-methyl-pyridine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51.4% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 110℃; for 2h;Inert atmosphere; To a solution of methyl 6-chloro-3-methyl-pyridine-2- carboxylate (1.0 g, 5.39 mmol) in 1,4-dioxane (17.9 ml) and H20 (2.9 ml) is added (3- (hydroxymethyl)phenyl)boronic acid (0.982 g, 6.47 mmol) followed by K2C03 (1.86 g, 13.47 mmol) and PdCl2(dppf)*CH2Cl2 (131.9 mg, 0.13 mmol). The reaction mixture is purged with argon for 5 minutes and then heated at 110C. After 2 hours, the reaction is cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated. The residue is purified by silica gel flash chromatography using 70% EtOAc in hexane to afford methyl 6-[3-(hydroxymethyl)phenyl]-3-metliyl-pyridine-2-carboxylate (0.713 g, 51.4%). Mass spectrum (m/z): 258.0 (M+l)+.
  • 8
  • [ 16932-45-9 ]
  • [ 87199-15-3 ]
  • (2',6'-dimethoxybiphenyl-3-yl)methanol [ No CAS ]
  • 9
  • [ 16932-45-9 ]
  • [ 87199-15-3 ]
  • 2,6-dimethoxy-2'-hydroxymethylbiphenyl [ No CAS ]
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