56467-43-7

Basic information

• Product Name: 4-benzoylphenyl 2-methylprop-2-enoate
• Synonyms: 2-propenoic acid, 2-methyl-, 4-benzoylphenyl ester; 4-Benzoylphenyl methacrylate
• CAS NO: 56467-43-7
• Molecular Formula: C₁₇H₁₄O₃
• Molecular Weight: 266.2913
• Mol File: 56467-43-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 418.2°C at 760 mmHg
• Flash Point: 185.6°C
• Density: 1.142g/cm³
• Vapor Pressure: 3.34E-07mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 4-benzoylphenyl 2-methylprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-benzoylphenyl 2-methylprop-2-enoate(56467-43-7)
• EPA Substance Registry System: 4-benzoylphenyl 2-methylprop-2-enoate(56467-43-7)

Safety Data

• Hazardous Substances Data: 56467-43-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Benzoylphenyl 2-methylprop-2-enoate is utilized as a key intermediate in organic synthesis for the production of a variety of compounds. Its reactivity allows for the creation of new chemical entities that can be used in different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-benzoylphenyl 2-methylprop-2-enoate serves as an important intermediate in the synthesis of various pharmaceuticals. Its unique structure contributes to the development of new drugs with potential therapeutic applications.
Used as a Photo-Initiator in Polymer and Coating Production:
4-Benzoylphenyl 2-methylprop-2-enoate is employed as a photo-initiator in the manufacturing process of polymers and coatings. Its ability to initiate polymerization reactions upon exposure to light makes it a crucial component in the production of these materials, enhancing their properties and performance.
Used in Agrochemical Synthesis:
This versatile chemical is also an intermediate in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products that can improve crop yields and protect plants from pests and diseases.

Synthetic route

methacryloyl anhydride (760-93-0) + 4-Hydroxybenzophenone (1137-42-4) → 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7)

Conditions	Yield
With 2,4-dimethyl-6-tert-butylphenol; sulfuric acid; 4-methoxy-phenol at 90℃; for 6h; Air introduction;	99.4%
With sulfuric acid In methanol at 90℃; for 2h; Temperature; Large scale;	99.7%
With tempol; 2,4-dimethyl-6-tert-butylphenol; 4-methoxy-phenol; magnesium bromide at 90℃; for 6h; Reagent/catalyst;

4-Hydroxybenzophenone (1137-42-4) + Methacryloyl chloride (920-46-7) → 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7)

Conditions	Yield
In acetone at 0℃;	90%
With triethylamine at 0 - 20℃; for 48h;	86%
With triethylamine In dichloromethane at 0 - 20℃; for 19h;	71.9%

methanol (67-56-1) + methacryloyl anhydride (760-93-0) + 4-Hydroxybenzophenone (1137-42-4) → methacrylic acid methyl ester (80-62-6) + 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7)

Conditions	Yield
Stage #1: methacryloyl anhydride; 4-Hydroxybenzophenone With 2,4-dimethyl-6-tert-butylphenol; sulfuric acid; 4-methoxy-phenol at 90℃; for 6h; Air introduction; Stage #2: methanol With sodium hydroxide In water at 60℃; for 1h;

methacrylic acid methyl ester (80-62-6) + 4-Hydroxybenzophenone (1137-42-4) → 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7)

Conditions	Yield
With methacryloyl anhydride; 2,4-dimethyl-6-tert-butylphenol; sodium methylate In methanol at 60 - 90℃; for 6h; Reagent/catalyst;	1320.4 g

N,N-Dimethylacrylamide (2680-03-7) + 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7) → polymer, Mw 155000 Da, Mw/Mn 2.5; monomer(s): N,N-dimethylacrylamide; 4-methacryloyloxybenzophenone

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 15h;

N,N-Dimethylacrylamide (2680-03-7) + 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7) → polymer, Mw 113000 Da, Mw/Mn 3.3; monomer(s): N,N-dimethylacrylamide; 4-methacryloyloxybenzophenone, 1.0 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 15h;

N,N-Dimethylacrylamide (2680-03-7) + 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7) → polymer, Mw 92800 Da, Mw/Mn 3.0; monomer(s): N,N-dimethylacrylamide; 4-methacryloyloxybenzophenone, 3.6 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 15h;

N,N-Dimethylacrylamide (2680-03-7) + 4-hydroxybenzophenone ester of metacrylic acid (56467-43-7) → polymer, Mw 134000 Da, Mw/Mn 5.4; monomer(s): N,N-dimethylacrylamide; 4-methacryloyloxybenzophenone, 14.3 mol percent

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) In N,N-dimethyl-formamide at 60℃; for 15h;

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 1137-42-4 4-Hydroxybenzophenone 
• 67-56-1 methanol 
• 760-93-0 methacryloyl anhydride 
• 920-46-7 Methacryloyl chloride 

Relevant articles and documents

The effect of the Hofmeister series on the deswelling isotherms of poly(N-isopropylacrylamide) and poly(N,N-diethylacrylamide)

The influence of Na2SO4, NaCl, NaBr, and NaI was studied on the deswelling isotherms of thin films of photo-crosslinked poly(N-isopropylacrylamide) and poly(N,N-diethylacrylamide) to help elucidate the mechanisms by which ions of the Hofmeister series affect the solubility of neutral, amide-based polymers. The films were characterized with both ellipsometry and FTIR to determine both water content and the frequency of the CO, N-H, and CH3 vibrations associated with the polymers. When compared at the same water content, the frequency of the N-H bend in poly(NIPAAm) red-shifts in the order I- > Cl- > Br- > SO42-. The red-shift is consistent with disrupted hydrogen bonding of the N-H moiety due to an ion-dipole attraction. The CO stretch on the other hand is insensitive to the ion, suggesting that the ion pairs primarily with the partially positive end of the HN-CO dipole. For poly(DEAAm), which lacks an N-H moiety, the CO stretch is now sensitive to the ion, with the trend following the order of the ion in the Hofmeister series. Both of these findings signify that I- > Cl- > Br- > SO42- with respect to the strength of the ion-dipole interaction. Moreover, the ion-dipole interaction is stronger in poly(NIPAAm) than poly(DEAAm), suggesting that the specificity of the Hofmeister ions arises from the effect of vicinal groups on the amide dipole. The Royal Society of Chemistry 2011.

Polymer Zwitterions for Stabilization of CsPbBr3 Perovskite Nanoparticles and Nanocomposite Films

Functional polymers with sulfobetaine or phosphorylcholine zwitterions as pendent groups are demonstrated as both ligands and host matrices for CsPbBr3 perovskite nanoparticles (PNPs). These polymers produce nanocomposite films with excellent NP dispersion, optical transparency, and impressive resistance to NP degradation upon exposure to water. Multidentate interactions of the zwitterion-containing copolymers with the PNPs induce dispersed or weakly aggregated nanocomposite morphologies, depending on the extent of zwitterionic functionality in the polymer. Incorporating additional functionality into the polymers, such as benzophenone pendent groups, yields lithographically patternable films, while time-resolved photoluminescence measurements provide insight into the electronic impact of PNPs in zwitterionic polymer matrices.

Swelling behavior of thin, surface-attached polymer networks

The swelling behavior of thin, surface-attached cross-linked dimethylacrylamide (DMAAm) films in contact with water has been characterized with multiple-angle nulling ellipsometry and compared to the swelling of nonattached, bulk DMAAm networks. The polymer networks are fabricated by cross-linking thin films of statistical copolymers composed of DMAAm and a photoreactive benzophenone derivative monomer. Covalent attachment of the film to the surface is achieved by means of a benzophenone-based silane monolayer. UV illumination simultaneously cross-links and chemically links the layer and chemically links the layer to the surface, forming stable networks that do not delaminate upon swelling. It is observed that the surface-attached networks swell less than the nonattached, bulk networks at the same cross-link density; however, the swelling of surface-attached networks is larger than that suggested by simple geometric considerations for swelling in one dimension. The results are in qualitative agreement with Flory-Rehner theory extended to one-dimensional swelling.

PREPARATION OF (METH)ACRYLIC ACID ESTERS

The invention relates to a method for preparation of (meth)acrylic acid esters from (meth)acrylic acid anhydrides.

METHOD FOR PREPARING KETO-FUNCTIONALIZED AROMATIC (METH)ACRYLATES

The invention relates to a method for preparing keto-functionalized aromatic (meth)acrylates by reacting keto-functionalized aromatic alcohols or keto-functionalized aromatic amines with (meth)acrylic anhydride having a content of (meth)acrylic acetic anhydride of less than 4.5%.

PHOTOACTIVATABLE FOULING-RESISTANT COPOLYMERS

A photoactivatable fouling-resistant copolymer composed of a photoactivatable monomer and a hydrophilic monomer is disclosed. The photoactivatable monomer includes an aryl ketone derivative having one or more polar groups or alkyl groups.

METHODS OF MAKING (ALK)ACRYLIC ESTERS IN FLOW REACTORS

A method of making an (alk)acrylic ester in a microflow reactor.

METHOD FOR PRODUCING METHACRYLATED BENZOPHENONES

The invention relates to a process for preparing methacrylic esters of hydroxyl-functional benzophenones and to their use. Methacrylated benzophenones (benzophenone (meth)acrylates) can be prepared in high purity by the process of the invention, in a simple way and in a high yield.

COPOLYMERIZABLE PHOTOINITIATORS

Benzophenone derivatives of formula (I) in which X is O, S or NR3, and R3 is H or linear or branched C1-C10 alkyl; R1 is H or methyl, R2 is H, halogen, linear or branched C1-C10 alkoxy, linear or branched C1-C10 alkyl, linear or branched C1-C10 alkylthio or a group NR4R5, wherein R4 and R5 are independently linear or branched C1-C10 alkyl, can be used as copolymerizable photoinitiators and photocrosslinkers.

METHOD FOR PRODUCING METHACRYLATED BENZOPHENONES

The invention relates to a method for producing methacrylated benzophenones and to the uses thereof.