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[ CAS No. 402-43-7 ] {[proInfo.proName]}

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Chemical Structure| 402-43-7
Chemical Structure| 402-43-7
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Product Citations

Product Citations      Expand+

Qiao Lin ; Ethan H. Spielvogel ; Tianning Diao DOI:

Abstract: The capture of carbon-centered radicals at a nickel(II) center is commonly featured in recent cross-coupling and metallaphotoredox catalytic reactions. Despite its widespread application in catalysis, this fundamental step lacks experimental characterization. This report portrays radical capture at catalytically relevant nickel(II) centers from several aspects, including the structure-activity relationships of the ligands, the mechanism, the kinetics, and the stereoselectivity. Spectroscopic data provide evidence for the formation of a nickel(III) intermediate. Strikingly different reactivity between nickel-aryl and nickel-alkyl complexes implies different rate-determining steps for C(sp3)–C(sp3) and C(sp2)–C(sp3) bond formation. Kinetic data benchmark the capture rates on the scale of 10[7] M?1s?1 and 10[6] M?1s?1 for primary and secondary radicals, respectively. Overall, the activation energy is higher than that of previous computational estimations. Finally, stoichiometric experiments with well-defined chiral nickel complexes demonstrate that the radical trapping step can confer diastereoselectivity and enantioselectivity with a drastic ligand effect.

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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 [ 402-43-7 ]

CAS No. :402-43-7 MDL No. :MFCD00000398
Formula : C7H4BrF3 Boiling Point : -
Linear Structure Formula :(F3C)C6H4Br InChI Key :XLQSXGGDTHANLN-UHFFFAOYSA-N
M.W : 225.01 Pubchem ID :67872
Synonyms :
Chemical Name :1-Bromo-4-(trifluoromethyl)benzene

Calculated chemistry of [ 402-43-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.14
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 4.62
Log Po/w (MLOGP) : 4.1
Log Po/w (SILICOS-IT) : 3.51
Consensus Log Po/w : 3.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.94
Solubility : 0.0257 mg/ml ; 0.000114 mol/l
Class : Soluble
Log S (Ali) : -3.45
Solubility : 0.0793 mg/ml ; 0.000352 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0162 mg/ml ; 0.0000719 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.16

Safety of [ 402-43-7 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P235-P501 UN#:1993
Hazard Statements:H225-H315-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 402-43-7 ]

* 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 [ 402-43-7 ]
  • Downstream synthetic route of [ 402-43-7 ]

[ 402-43-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 402-43-7 ]
  • [ 75927-49-0 ]
  • [ 1242770-50-8 ]
Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 8, p. 3172 - 3176
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