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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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Modulation of Host-Guest Complexation of Pfas with Ph Ionizable Β-Cyclodextrin Derivatives
O' ; Shea, KE ; Restrepo-Osorio, Rodrigo ;
Abstract: Poly- and perfluoroalkyl substances (PFAS) are pollutants of serious concern due to their adverse health effects, widespread use, and resistance to degradation. β-cyclodextrins (β-CDs) form strong β-CD:PFAS complexes with a wide variety of PFAS. We report herein the incorporation of ionizable functional groups on the primary rim of β-CD, to control the complexation of PFAS as a function of solution pH. The binding constants (KCD:PFAS) of short-chain and long-chain PFAS by amino-β-CDs and thiol-β-CDs decrease by 56 to 98 % with a change in solution pH from neutral to alkaline conditions. The observed reduction in binding constants (KCD:PFAS) with increased pH is assigned to the increased electrostatic repulsion between negatively charged functional group amended to the β-CD (host) and negatively charged PFAS polar head group (guest) under alkaline conditions. The inclusion of two pH-dependent ionizable functional groups to the host was achieved by employing 6-(3-hydroxybenzylamino)-6-deoxy-β- cyclodextrin [(3-OH)BnNHβ-CD]. The phenol functionality is converted from a neutral to an anionic species while the benzyl-amino group is cationic under neutral pH and converted to neutral charge under alkaline conditions, thus the β-CD host can be converted from a positive charge to a negative charge by varying solution pH. The (3-OH)BnNHβ-CD exhibits strong pH-modulated binding with long-chain perfluorocarboxylic acids (PFCAs), evidenced in an 88 % decrease in the association constant with PFOA 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 binding. 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.
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Keywords: Host-guest complexation ; PFAS ; cyclodextrin ; remediation: pH
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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Tags: 2-(Aminomethyl)phenol | 2-Hydroxybenzylamine | Amines | ROS | Organic Building Blocks | Tumor Metabolism | Immunology/Inflammation | Parkinson'S Disease and Alzheimer'S Disease | PPAR Signaling Pathway | Endoplasmic Reticulum Stress | 932-30-9
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P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
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P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
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P405 | Store locked up. |
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H201 | Explosive; mass explosion hazard |
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H203 | Explosive; fire, blast or projection hazard |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
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H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
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H260 | In contact with water releases flammable gases which may ignite spontaneously |
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H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
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H318 | Causes serious eye damage |
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H401 | Toxic to aquatic life |
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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