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[ CAS No. 224311-51-7 ] {[proInfo.proName]}

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Chemical Structure| 224311-51-7
Chemical Structure| 224311-51-7
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Product Citations

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Sims, C.B. ; Chandler, E.T. ; Espitia Armenta, H. , et al. DOI:

Abstract: The development, analysis, characterization, and solvent preference of photo-responsive hybrid 4,4’-divinylazobenzene and octa(dimethylsiloxy)silsesquioxane (Q8M8 H) networks were investigated. The dynamic gel systems are formed through hydrosilylation chemistry and react to visible and UV light to expand and contract, giving them sponge-like properties. Their solvent preference and loading capabilities are analyzed and compared to an analogous system, and general characteristics are illustrated through FTIR, TGA, DMA, and SEM imaging. We find that using a shorter, more rigid azobenzene results in a comparable photo-responsive sponge with a higher initial shrinkage response.

Keywords: 4,4’-Divinylazobenzene ; Photoactuatable ; Smart-gels ; Sponge ; Azobenzene

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Cory Blake Sims ;

Abstract: The development of hybrid organosilicon materials as both rapid curing coatings and photo-responsive sponges has been conducted utilizing silsesquioxane (SQ) based chemistries for the robustness they provide in the final materials. Additional research was conducted on the formation of sulfur-based SQ analogs. Chapter I will provide background about the synthesis of silsesquioxanes, their properties, and the favorability for three-dimensional material formation using these molecules. Additional information will include challenges and histories of siloxane based protective coatings and the use of both photo-radical and photo-acid-generating initiators in them, along with a brief explanation of photo-switches, specifically azobenzene and its derivatives and their use in sol-gels. Chapter II will discuss protective coatings for monuments and the specific needs associated with these materials. A history of the types of materials used and their faults will detail the desire for new materials aimed at this application. The development of a coating with three distinct curing methods (including photo-radical and photo-acid generating processes) which forms a protective layer with a mixture of partially formed polisilsesquioxane and oligosilsesquioxane structures as the backbone of the network. Findings and properties of the resulting coating formulations, modifiability, and alternative functionalities will be discussed in detail. Chapter III will discuss the use of photo-switches as crosslinkers in silicon-based networks. Previous work utilized Q-type silsesquioxanes (Q8M8H) and 4,4’-diallyloxyazobenzene (DAA) to develop photodynamic sponges. The modification process of these sponge materials, through both in-situ and post-polymerization functionalization, will be described. The effects on solvent preference resulting from the modifications will describe “sponge” uptake and swell-ability in various environmental pollutants. Chapter IV discusses the synthesis, characterization, and overall performance of an analog Q8M8H sponge system using 4,4’-divinylazobenzne (DVA), in place of 4,4’-diallyloxyazobenzene. Analysis of the resulting changes in swelling efficiency and solvent preference will be provided. Chapter V will describe the investigation into new species of organosilicon compounds. This chapter will detail early work on synthesizing novel silicon-sulfur silsesquioxane analogs, including the methods, challenges, and findings in this underdeveloped field. Chapter VI will provide an overview of the results, findings, and lessons learned through the research above.

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Product Details of [ 224311-51-7 ]

CAS No. :224311-51-7 MDL No. :MFCD01862440
Formula : C20H27P Boiling Point : No data available
Linear Structure Formula :C12H9P(C(CH3)3)2 InChI Key :CNXMDTWQWLGCPE-UHFFFAOYSA-N
M.W : 298.40 Pubchem ID :2734215
Synonyms :
Chemical Name :2-(Di-tert-Butylphosphino)biphenyl

Calculated chemistry of [ 224311-51-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.4
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 99.08
TPSA : 13.59 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.76
Log Po/w (XLOGP3) : 5.09
Log Po/w (WLOGP) : 6.06
Log Po/w (MLOGP) : 5.86
Log Po/w (SILICOS-IT) : 6.47
Consensus Log Po/w : 5.45

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.06
Solubility : 0.00263 mg/ml ; 0.0000088 mol/l
Class : Moderately soluble
Log S (Ali) : -5.12
Solubility : 0.00227 mg/ml ; 0.00000761 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.43
Solubility : 0.000011 mg/ml ; 0.0000000367 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.93

Safety of [ 224311-51-7 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319-H413 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 224311-51-7 ]

* 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.

  • Downstream synthetic route of [ 224311-51-7 ]

[ 224311-51-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 13716-10-4 ]
  • [ 2052-07-5 ]
  • [ 224311-51-7 ]
YieldReaction ConditionsOperation in experiment
95.7% Under nitrogen protection,1L three bottles,From 40 g of 2-bromobiphenyl,5 g of magnesium turnings and 400 ml of anhydrousTHF to produce Grignard reagent,Refluxed for 2 hours,Down to room temperature,2 g of tetrakis (triphenylphosphine) palladium was added,Stirred for 30 minutes,33 g of di-tert-butylphosphonium chloride was added dropwise at room temperature,The reaction was refluxed for 2 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched,Liquid separation,The organic phase is dissolved,Add methanol crystallization,Filtration gave 49 g of white 2- (di-tert-butylphosphine) biphenyl, and the yield was 95.7percent.
  • 2
  • [ 622391-65-5 ]
  • [ 224311-51-7 ]
  • [ 622391-71-3 ]
YieldReaction ConditionsOperation in experiment
17% palladium diacetate; In hexane; toluene; Part J. Preparation of 1-cyclopropyl-4-{4-[3-fluoro-4-(4,4,4-trifluoro-butyl)-phenyl]-piperazine-1-sulfonyl}-piperidine-4-carboxylic Acid tert-butyl Ester A mixture of the product of Part I (2.78 g, 6.22 mmol), the product of Part C (1.80 g, 7.48 mmol), palladium(II) acetate (0.070 g, 0.312 mmol), sodium t-butoxide (0.836 g, 8.69 mmol), and 2-(di-t-butylphosphino)biphenyl (0.185, 0.621 mmol) in toluene was heated at 90° C. for 18 hr. The mixture was then diluted with water (350 mL) and extracted with ethyl acetate (3*100 mL). The organic layer was filtered through celite, washed with water (2*100 mL) and brine (100 mL), dried over MgSO4, and concentrated in vacuo to afford a yellow oil. The oil was purified on silica gel (70 g), eluding with 0-100percent ethyl acetate in hexane, to afford 0.638 g (17percent yield) of the desired compound in the form of a yellow oil. MS: m/z=578 (M+H).
  • 3
  • [ 224311-51-7 ]
  • 2-(di(tert-butyl)phosphinyl)biphenyl [ No CAS ]
  • 4
  • [ 224311-51-7 ]
  • [ 719275-59-9 ]
YieldReaction ConditionsOperation in experiment
80% With copper(ll) bromide; In methanol; for 0.25h;Heating / reflux; 50 ml entgastes, wasserfreies Methanol wurde auf Rueckflusstemperatur erhitzt, 2,36 g (7,9 mmol) 2-(Di-tert.-butylphosphino)biphenyl wurde langsam dem Methanol zugegeben, bis die Phosphin-Verbindung vollstaendig geloest war. Anschliessend wurde 0,59 g (2,6 mmol) Kupfer(II)-bromid portionsweise der Loesung zugegeben. Nach Zugabe des Kupferbromids wurde die Loesung noch weitere 15 min lang auf Rueckflusstemperatur erhitzt und danach die Loesung abgekuehlt. Nach Abkuehlen der Loesung fiel ein Feststoff aus, der abfiltriert wurde und mit wenig Ethanol und Diethylether gewaschen und anschliessend getrocknet wurde. Man erhielt 0,93 g (1,1 mmol) der oben genannten Verbindung. Die Ausbeute betrug 80 percent d. Th.
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