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

General Description

4-benzoylphenyl 2-methylprop-2-enoate is an organic compound with the chemical formula C20H18O3. It belongs to the class of benzoylphenyl esters and is commonly used in the field of organic synthesis and pharmaceutical research. 4-benzoylphenyl 2-methylprop-2-enoate is a derivative of benzophenone and is known for its use as a photo-initiator in the production of polymers and coatings. It is also an important intermediate in the synthesis of various pharmaceuticals and agrochemicals. 4-benzoylphenyl 2-methylprop-2-enoate is a versatile chemical that finds applications in a wide range of industries due to its reactivity and unique properties.

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

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

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.

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.

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%.

METHODS OF MAKING (ALK)ACRYLIC ESTERS IN FLOW REACTORS

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