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Chemical Structure| 932-30-9 Chemical Structure| 932-30-9
Chemical Structure| 932-30-9

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2-(Aminomethyl)phenol is a selective dicarbonyl scavenger with antioxidant and free radical scavenging capabilities, used in studies of inflammation and cardiovascular diseases.

Synonyms: 2-Hydroxybenzylamine; o-Hydroxybenzylamine; NSC 127870

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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

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Product Details of 2-(Aminomethyl)phenol

CAS No. :932-30-9
Formula : C7H9NO
M.W : 123.15
SMILES Code : OC1=CC=CC=C1CN
Synonyms :
2-Hydroxybenzylamine; o-Hydroxybenzylamine; NSC 127870
MDL No. :MFCD00870498
InChI Key :KPRZOPQOBJRYSW-UHFFFAOYSA-N
Pubchem ID :70267

Safety of 2-(Aminomethyl)phenol

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

Application In Synthesis of 2-(Aminomethyl)phenol

* 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 [ 932-30-9 ]

[ 932-30-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 932-30-9 ]
  • [ 112811-71-9 ]
  • C23H23FN2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 120℃; for 6h; Three-necked flask was charged with 100 g of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate,Adding 600mL of acetonitrile, stirring, adding 2-hydroxybenzylamine 37mL, heating to 120 C for 6h, cooling, pouring the reaction solution into 1mol / L dilute hydrochloric acid, stirring, adding 500mLEA extraction,The aqueous phase was extracted with EA 300 mL × 2 and the organic layers were combined, dried and evaporated to dryness to give 92.3 g of the yellow product which was used in the next step without further purification.
  • 2
  • [ 1206675-01-5 ]
  • [ 932-30-9 ]
  • 3
  • [ 932-30-9 ]
  • [ 64-19-7 ]
  • [ 1206675-01-5 ]
YieldReaction ConditionsOperation in experiment
35.4 g 9. The dried solid was dissolved in 420 g of glacial acetic acid and stirred for 16-24 hours.10. To the reaction system, 932 g of methyl tert-butyl ether was added, and the mixture was stirred and crystallized at 0 to 10 C for 4 to 6 hours.11. Centrifuge the system, centrifuge the solids with 250 ml of 85% ethanol and centrifuge again.12. Centrifuge the solid at 40-50 C to dry, to obtain the final product 35.4g, white.
 

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