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[ CAS No. 262-12-4 ] {[proInfo.proName]}

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Chemical Structure| 262-12-4
Chemical Structure| 262-12-4
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Product Citations

Product Citations

Gustavo Mu?oz ; Kari M. Chamberlain ; Maxim E. Solovyev , et al. DOI:

Abstract: Since the seminal work presented by Olah in 1966 on fluorinated carbocations, several strategies have been presented to introduce fluorinated moieties in polymer backbones via carbocation chemistry. The hexafluoroisopropylidene (6F) group is well known for its ability to enhance thermal properties and processability of polymers. However, its direct electrophilic incorporation into polymers has been largely ignored due to the challenges posed by activating hexafluoroacetone monomer for electrophilic aromatic substitution (EAS). In this article, we review the role of fluorinated carbocations from 1966 up to our recent versatile fluoroalkylation strategy to directly enchain the 6F group in polymers. Via EAS interfacial polymerization we reacted hexafluoroacetone trihydrate (HFAH) with aromatic monomers in triflic anhydride (Tf2O) and 1,2-dichloroethane (DCE) with Aliquat? 336. In addition, the polymerization of dibenzo-1,4-dioxin with HFAH is presented. A semi-fluorinated diol, 4,4′-bis(2-hydroxyhexafluoroisopropyl)diphenyl ether, was synthesized by this method and used to prepare the first reported polycarbonate with hexafluoroisopropoxy groups –C(CF3)2O– incorporated in the main chain via polycondensation. Polysilyl ethers were also prepared from this diol. Additionally, we briefly mention Carraher’s legacy in the synthesis of metal-containing polymers via reactions of group IVB metallocene dichloride with dinucleophiles (diamines, diol, dicarboxylic acids, and dithiols) in solution and interfacial conditions in terms of electrophilic vs nucleophilic polycondensation. The new acidic, sterically hindered semi-fluorinated diol and bisphenol AF were reacted with group IVB metallocene dichloride in attempts to form metallocene condensation polymers with improved solubility.

Keywords: Semi-fluorinated polyaryl ether ; Electrophilic polymerization ; Fluorinated diol ; Fluorinated metallopolymer ; Hexafluoroacetone trihydrate ; High-performance polymer

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Product Details of [ 262-12-4 ]

CAS No. :262-12-4 MDL No. :MFCD00022282
Formula : C12H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NFBOHOGPQUYFRF-UHFFFAOYSA-N
M.W : 184.19 Pubchem ID :9216
Synonyms :

Calculated chemistry of [ 262-12-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.03
TPSA : 18.46 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.53
Log Po/w (XLOGP3) : 4.3
Log Po/w (WLOGP) : 3.58
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 3.02
Consensus Log Po/w : 3.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.33
Solubility : 0.00871 mg/ml ; 0.0000473 mol/l
Class : Moderately soluble
Log S (Ali) : -4.4
Solubility : 0.00732 mg/ml ; 0.0000397 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.39
Solubility : 0.00754 mg/ml ; 0.0000409 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.55

Safety of [ 262-12-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312+P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 262-12-4 ]

* 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 [ 262-12-4 ]

[ 262-12-4 ] Synthesis Path-Downstream   1~1

  • 1
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  • [ 39073-07-9 ]
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