Home Cart Sign in  
Chemical Structure| 81644-55-5 Chemical Structure| 81644-55-5

Structure of 81644-55-5

Chemical Structure| 81644-55-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Restrepo-Osorio, Rodrigo A ; O’Shea, Kevin E ;

Abstract: Poly- and perfluoroalkyl substances (PFAS) are organic pollutants whose widespread use, resistance to degradation, and adverse health effects have raised significant environmental and public health concerns. The ability of β-cyclodextrin (β-CD) to form strong inclusion complexes with PFAS has led to its incorporation in adsorbents for treating PFAS-contaminated water. Regenerating these PFAS-laden materials often remains challenging. We report herein the functionalization of β-CD with ionizable groups to control host-guest complexation with PFAS in response to pH changes. Adjusting the solution pH from neutral to alkaline led to a 56 to 98 % reduction in the binding constants (KCD:PFAS) of short- and long-chain PFAS with amino- and thiol-functionalized β-CDs. The observed reduction in binding constants under alkaline conditions is attributed to enhanced electrostatic repulsion between negatively charged functional groups attached to β-CD (host) and the anionic PFAS polar head group (guest). Incorporation of two pH-dependent ionizable functional groups, phenol and benzylamino, into β-CD to yield 6-(3-hydroxybenzylamino)-6-deoxy-β-cyclodextrin [(3-OH)BnNHβ-CD] enables the β-CD host to transition from a positive to a negative charge as the solution pH increases from neutral to alkaline. Consequently, (3-OH)BnNHβ-CD exhibits a pronounced pH-modulated complexation of PFOA, with an 88 % decrease in the association constant under alkaline conditions. The association constant for (3-OH)BnNHβ-CD with hexafluoropropylene oxide dimer acid (HFPO-DA), a branched perfluoroether carboxylic acid (PFECA), however, decreases by nearly 50 % under alkaline conditions compared to an 81 % and 98 % decrease observed for mono-thiol and mono-amino β-CDs, respectively. A 95 % decrease in binding in PFOA is observed for mono-thiol-β-CD, while heptakis-(6-mercapto-6-deoxy)-β-cyclodextrin, with seven ionizable thiol groups, leads to a modest 23 % decrease for complexation of PFOA with change from neutral to alkaline pH. Steric effects due to chain branching within PFAS in combination with size and number of substituents on the β-CD reduce the impact of pH effects on the complexation. This study demonstrates derivatization of β-CD with pH ionizable functional groups can be used to control the β-CD binding of PFAS as a possible strategy for the removal and recovery of PFAS from contaminated water streams.

Keywords: Host-guest complexation ; PFAS ; β-cyclodextrin ; Remediation ; pH

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 81644-55-5 ]

CAS No. :81644-55-5
Formula : C42H70O34S
M.W : 1151.05
SMILES Code : OC[C@@H]1[C@]2([H])[C@@H]([C@@H](O)[C@](O[C@]3([H])[C@H](O[C@@](O[C@]4([H])[C@H](O[C@@](O[C@]5([H])[C@H](O[C@@](O[C@@]6([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]6CO)([H])O[C@@]7([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]7CO)([H])O[C@@]8([H])[C@H](O)[C@@H](O)[C@@](O[C@@H]8CO)([H])O2)([H])[C@H](O)[C@H]5O)CS)([H])[C@H](O)[C@H]4O)CO)([H])[C@H](O)[C@H]3O)CO)([H])O1)O
MDL No. :MFCD31537208
InChI Key :KBQFCFNGXZCYMC-FOUAGVGXSA-N
Pubchem ID :10931212

Safety of [ 81644-55-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 81644-55-5 ]

* 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 [ 81644-55-5 ]

[ 81644-55-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 67217-55-4 ]
  • [ 81644-55-5 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With sodium hydroxide; thiourea In water at 80℃; for 9 h;
Stage #2: With hydrogenchloride In water at 20℃;
A 50 mL round bottom flask with a magnetic stirbar and a Schlenk adapter was charged with 1.00 g (0.776 mmol) of 19, 0.59 g (7.75 mmol) of thiourea (Aldrich) and 7.8 mL of 0.1N NaOH solution. The resulting mixture was heated at 80 °C for 6 hours under nitrogen. Next, 0.62g (15.5 mmol) of sodium hydroxide was added and the reaction mixture was heated at 80 °C under nitrogen for another hour. The reaction was allowed to cool to room temperature before it was brought to pH 4.0 with 10percent HCl. The total solution volume was brought to 20 mL and then was cooled in an ice bath before 0.8 mL of tetrachloroethylene was added. The reaction mixture was stirred vigorously at 0 °C for 0.5 h before the precipitated solid was collected in a fine glass frit. The solid was pumped down overnight to yield 0.60 g (67percent) of a white amorphous solid.
References: [1] Chemistry - A European Journal, 2014, vol. 20, # 35, p. 10944 - 10952.
[2] Patent: EP1133318, 2007, B1, . Location in patent: Page/Page column 32-33.
[3] Chinese Journal of Chemistry, 2017, vol. 35, # 7, p. 1125 - 1132.
[4] Chemical Communications, 2011, vol. 47, # 45, p. 12388 - 12390.
[5] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 450 - 454.
[6] Journal of the American Chemical Society, 1996, vol. 118, # 21, p. 5039 - 5046.
[7] Journal of the American Chemical Society, 2009, vol. 131, p. 1386 - 1387.
[8] Chemical Communications, 2010, vol. 46, # 23, p. 4094 - 4096.
[9] Journal of Materials Chemistry A, 2014, vol. 2, # 25, p. 9587 - 9593.
[10] New Journal of Chemistry, 2018, vol. 42, # 5, p. 3593 - 3601.
[11] ChemPhysChem, 2019, vol. 20, # 7, p. 984 - 990.
  • 2
  • [ 67217-55-4 ]
  • [ 17356-08-0 ]
  • [ 81644-55-5 ]
References: [1] Tetrahedron Letters, 2007, vol. 48, # 52, p. 9185 - 9189.
[2] Chemistry - A European Journal, 2013, vol. 19, # 32, p. 10526 - 10535.
[3] Chemical Communications, 2015, vol. 51, # 30, p. 6512 - 6514.
[4] Tetrahedron Letters, 1994, vol. 35, # 25, p. 4275 - 4278.
  • 3
  • [ 7585-39-9 ]
  • [ 81644-55-5 ]
References: [1] New Journal of Chemistry, 2015, vol. 39, # 1, p. 555 - 565.
 

Historical Records

Categories