937-41-7|Phenyl acrylate| Ambeed

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Quality Control of [ 937-41-7 ] Purity: 97% (stabilized with BHT) SDS Specification

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Anion exchange membranes based on (3-acrylamidopropyl) trimethylammonium chloride (APTA) and phenyl Acrylate: Impact of crosslinker and crosslinker content on physiochemical properties and transport behavior of acetate and formate

Lin, Yi-hung ; Clinch, McKenna F ; Beckingham, Bryan S ;

DOI: 10.1016/j.eurpolymj.2025.114035 Eur. Polym. J.,2025,114035.

Abstract: CO₂ reduction cells are innovative devices that convert CO₂ into valuable chemicals, such as formate (OFm^-) and acetate (OAc^-), at the cathode. One of the key challenges in these devices is the development of ion exchange membranes that enable the transport of charge carriers between electrodes while minimizing the transfer of CO₂ reduction products. This study focuses on the preparation and characterization of crosslinked anion exchange membranes (AEMs) made of phenyl acrylate (PA) and (3-acrylamidopropyl) trimethylammonium chloride (APTA), crosslinked with either poly(ethylene glycol) diacrylate (PEGDA) or N,N’-methylenebisacrylamide (MBAA). The membranes are characterized to understand their physiochemical properties and corresponding transport behavior through characterization of water volume fraction, mechanical properties, ionic conductivity, ion exchange capacity, water contact angle, glass transition temperature as well as their permeability and solubility to formate and acetate. MBAA crosslinked membranes exhibit higher Young’s modulus and lower strain at break compared to PEGDA-crosslinked membranes, which is attributed to their shorter chain length. Within a series of membranes of varied comonomer content, for either PEGDA or MBAA as crosslinker, permeabilities generally follow free volume theory (increasing permeability with increasing water content where water content increases with decreasing crosslinker content). Interestingly, for membranes with different crosslinkers but analogous water volume fraction significant differences (∼2 orders of magnitude) in permeability are observed which we attribute to differences in chain mobility as characterized through the glass transition temperature.

Purchased from AmBeed: 937-41-7

Development of Structure–Property Relationships for Ammonium Transport through Charged Organogels

Adam L. Bachmann ; Brock Hunter ; Bryan S. Beckingham ;

DOI: 10.3390/membranes14030071 Membranes,2024,14(3):71.

Abstract: Ammonia is a promising carbon-free fuel, but current methods to produce ammonia are energy intensive. New methods are thereby needed, with one promising method being electrochemical nitrogen reduction cells. Efficient cell operation requires robust catalysts but also efficient membrane separators that permit the selective transport of ions while minimizing the transport of the products across the cell. Commercial membranes have an unknown morphology which makes designing improved cells challenging. To address this problem, we synthesized a series of membranes with controlled crosslinking density and chemical composition to understand their impact on ammonium transport. Higher crosslinking density led to lower ammonium permeability. At the highest crosslinking density, similar ammonium permeability was observed independent of the water volume fraction and hydrophobicity of the monomers. These results suggest new directions to develop membranes with reduced ammonium crossover to improve the efficiency of these electrochemical cells.

Keywords: cation exchange membrane ; sulfonic acid ; nitrogen reduction

Purchased from AmBeed: 937-41-7

Salt Transport in Crosslinked Hydrogel Membranes Containing Zwitterionic Sulfobetaine Methacrylate and Hydrophobic Phenyl Acrylate

Lin, Yi-hung ; Kim, Jung Min ; Beckingham, Bryan S. ;

DOI: 10.3390/polym15061387 PubMed ID: 36987167 Polymers,2023,15(6):1387.

Abstract: Produced water is a byproduct of industrial operations, such as hydraulic fracturing for increased oil recovery, that causes environmental issues since it includes different metal ions (e.g., Li+, K+, Ni2+, Mg2+, etc.) that need to be extracted or collected before disposal. To remove these substances using either selective transport behavior or absorption-swing processes employing membrane-bound ligands, membrane separation procedures are promising unit operations. This study investigates the transport of a series of salts in crosslinked polymer membranes synthesized using a hydrophobic monomer (Ph acrylate, PA), a zwitterionic hydrophilic monomer (sulfobetaine methacrylate, SBMA), and a crosslinker (methylenebisacrylamide, MBAA). Membranes are characterized according to their thermomech. properties, where an increased SBMA content leads to decreased water uptake due to structural differences within the films and to more ionic interactions between the ammonium and sulfonate moieties, resulting in a decreased water volume fraction, and Young′s modulus increases with increasing MBAA or PA content. Permeabilities, solubilities, and diffusivities of membranes to LiCl, NaCl, KCl, CaCl2, MgCl2, and NiCl2 are determined by diffusion cell experiments, sorption-desorption experiments, and the solution-diffusion relationship, resp. Permeability to these metal ions generally decreases with an increasing SBMA content or MBAA content due to the corresponding decreasing water volume fraction, and the permeabilities are in the order of K+ > Na+ > Li+ > Ni2+ > Ca2+ > Mg2+ presumably due to the differences in the hydration diameter

Keywords: zwitterionic membranes ; salt transport ; phenyl acrylate ; crosslinked

Purchased from AmBeed: 937-41-7

Improved Structural Stability of Charged Hydrogels under Organic CO2 Reduction Products: Effect of Acrylate and Methacrylate Backbone Linkages

Kim, Jung Min ; Lin, Yi-hung ; Bannon, Sean M. ; Geise, Geoffrey M. ; Beckingham, Bryan S. ;

DOI: 10.1021/acs.jpcc.3c01854 J. Phys. Chem. C,2023,127(22):10826-10832.

Abstract: Understanding the mixed solute transport behavior of CO2 reduction products (methanol and formate) in ion exchange membranes (IEMs) is of interest for CO2 reduction cells (CO2RCs). The role of an IEM in a typical CO2RC is to suppress the crossover of all CO2 reduction products while allowing the transport of electrolytes. Tuning the polymer rigidity of the membrane is a key contributor to such highly controlled transport of organic solutes in a dense hydrated membrane. Here, we study the mixed solute transport behavior of methanol and formate in a series of tough Ph acrylate-based cross-linked IEMs. We then study the effects of a structural modification on mixed solute transport behavior by introducing quaternary carbons within the membrane. We measured the relative permittivity properties of swollen films to determine if the water hydrogen bonding environment within the IEMs, which is related to maintaining selective ion transport within the membrane (electrolytes over CO2 reduction products), was impacted by various organic solutes. We observed films with methacrylate backbone linkages have effectively constant relative permittivities when exposed to solutions containing methanol, formate, and a mix thereof. These findings may assist in designing membranes for applications, including CO2 reduction cells and water-organic separation

Purchased from AmBeed: 937-41-7

Alcohol-carboxylate transport in phenyl-based membranes of varying chain length transport

Membrane science ; Polymer chemistry ; Ion exchange membranes ; Multi-solute transport ; Charge screening ; Crosslinked membranes

Abstract: As global climate change is a major concern which is accelerated by CO2 emissions, we need to reduce CO2 emissions from the environment. In order to do that, researchers conceptualized CO2 reduction cells which electrochemically convert CO2 to other chemicals such as CO or methanol. A major problem faced by such devices is the crossover of the CO2 reduction products (i.e. methanol (MeOH), formate (OFm-), and acetate (OAc-)) through ion exchange membranes (IEM) which reduces the efficiency of the cell. Therefore, it is critical to design IEMs that suppress the transport of CO2 reduction products. Towards this goal, our group has been investigating the transport behavior of these products in crosslinked PEGDA-based IEMs, where we observed the diffusivities of cation exchange membranes to OFm- and OAc- increased in co-diffusion with MeOH, which is a concerning behavior. Here, we prepared analogous films with a series of phenyl- containing comonomers of different chain lengths [i.e. phenyl acrylate (PA, n = 0), phenyl ether acrylate (PEA, n = 1), and poly(ethylene glycol) phenyl ether acrylate (PEGPEA, n = 3)]. We then measured the permeabilities of these films toto OFm- and OAc-, where we observed the permeabilities of films with the shorter chain length [PEGDA-PA (n = 0)] to be lower than films with longer comonomer chain lengths. This work lays the foundation for further understanding of transport in these films, where in the future we will measure permeabilities to MeOH, cotransport MeOH-OFm-, and MeOH-OAc- as well as the solubilities of these species within the films.

Purchased from AmBeed: 937-41-7

Fabrication and Characterization of Cross-Linked Phenyl-Acrylate-Based Ion Exchange Membranes and Performance in a Direct Urea Fuel Cell

Jung Min Kim ; Yuyang Wang ; Yi-hung Lin ; Jaesik Yoon ; Tina Huang ; Dong-Joo Kim , et al.

DOI: 10.1021/acs.iecr.1c02798 Ind. Eng. Chem. Res.,2021,60(41):14856-14867.

Abstract: Ion exchange membranes (IEMs) are crucial for direct fuel cells, including direct methanol and direct urea fuel cells (DUFCs). While commercially available IEMs (e.g., FAA-3-50) show decent power density in direct fuel cells, they experience considerable methanol or urea crossover, reducing device performance and motivating design of IEMs that suppress fuel crossover. Here, we prepare cross-linked IEMs with high mechanical toughness utilizing a cross-linker (methylenebis(acrylamide)), hydrophobic monomer (phenyl acrylate (PA) or phenyl methacrylate (PMA)), and charged monomer (2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) for cation exchange or methacroylcholine chloride (MACC) for anion exchange). To validate these membranes in a fuel cell application, we perform DUFC experiments utilizing a PA/MACC AEM and observe good power density compared to FAA-3-50. To understand the role of urea crossover in DUFC performance, permeabilities of both membranes to urea are measured by diffusion cells with in situ ATR-FTIR spectroscopy, where our PA/MACC exhibited lower urea permeability than FAA-3-50.

Purchased from AmBeed: 937-41-7

Emergent Transport in Ion Exchange Membranes

Kim, Jung Min ;

Abstract: The ion exchange membrane (IEM) is a crucial part of various applications from water purification (i.e. electrodialysis) to energy conversion (i.e. photoelectrochemical CO2 reduction cells (PEC-CRC) and direct urea fuel cells (DUFC)). Theoretically, these approaches are more profitable and eco-friendly than their alternatives, such as distillation and fossil fuels. However, a major drawback of these applications is the selectivity of existing IEMs not being adequate (i.e. crossover of undesired solutes). Moreover, each application requires a different membrane specification. For instance, membranes for PEC-CRCs should be minimizing the crossover of CO2 reduction products (i.e. methanol (MeOH), ethanol (EtOH), formate (OFm-), acetate (OAc-)), while allowing the permeation of electrolytes (i.e. bicarbonate (HCO3-)). In the case of DUFC, membranes should minimize the crossover of urea to avoid catalyst sweeping effect. To design target-specific membranes, we took three series of investigations, which are (1) understanding alcohol-carboxylate co-transport behavior in IEMs, (2) analyzing the impact of charge-neutral comonomers in cation exchange membranes (CEM), and (3) introducing a new class of IEMs. From the first series, we conjectured a charge screening behavior based on the carboxylate diffusivity of CEMs being increased and that of anion exchange membranes (AEM) being decreased in co-diffusion with an alcohol. From the second series, we conjectured the interaction between different two dissimilar pendant groups on polymer network can offset the charge screening behavior in CEMs, where the carboxylate diffusivity in CEMs with sulfopropyl groups and poly(ethylene glycol) phenyl ether (PEGPE) groups being consistent in co-diffusion with alcohol. From the third series, we introduced a new class of crosslinked IEMs with phenyl acrylate (hydrophobic monomer). More findings from each series of investigations will be discussed in corresponding sections.

Keywords: Membrane science ; Polymer chemistry ; Ion exchange membranes ; Multi-solute transport ; Charge screening ; Crosslinked membranes

Purchased from AmBeed: 937-41-7

Product Details of [ 937-41-7 ]

CAS No. :	937-41-7
Formula :	C₉H₈O₂
M.W :	148.16
SMILES Code :	C=CC(OC1=CC=CC=C1)=O
MDL No. :	MFCD00048145
InChI Key :	WRAQQYDMVSCOTE-UHFFFAOYSA-N
Pubchem ID :	61242

Safety of [ 937-41-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H319-H372-H410
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330
Class:	9
UN#:	3082
Packing Group:	Ⅲ

Computational Chemistry of [ 937-41-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	42.27
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.04
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.08
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.78
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.16
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.02
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.02

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.27
Solubility	0.787 mg/ml ; 0.00531 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.26
Solubility	0.811 mg/ml ; 0.00547 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.51
Solubility	0.456 mg/ml ; 0.00308 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.73 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.47

Application In Synthesis of [ 937-41-7 ]

* 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 [ 937-41-7 ]

[ 937-41-7 ] Synthesis Path-Downstream 1~1

1
[ 19012-02-3 ]
[ 937-41-7 ]
phenyl (E)-3-(3-acetyl-1-methyl-1H-indol-2-yl)acrylate [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 5496 - 5499.

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 937-41-7 ]

Esters

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A633660 [73839-82-4]

Di(naphthalen-(Z)-2-yl) maleate

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A525305 [2177-70-0]

Phenyl methacrylate

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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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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CAS No.: 937-41-7

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