22535-49-5

Basic information

• Product Name: 2-Propenoic acid,4-benzoylphenyl ester
• Synonyms: 2-Propenoic acid, 4-benzoylphenyl ester;2-Propenoic acid,4-benzoylphenyl ester;4-Acryloyloxybenzophenone;4-Acryloxybenzophenone;4-Benzoylphenyl acrylate
• CAS NO: 22535-49-5
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.26
• Mol File: 22535-49-5.mol

Chemical Properties

• Melting Point: 48.5 °C(Solv: hexane (110-54-3))
• Boiling Point: 407.043 °C at 760 mmHg
• Flash Point: 181.355 °C
• Appearance: /
• Density: 1.164 g/cm³
• Vapor Pressure: 7.77E-07mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Propenoic acid,4-benzoylphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid,4-benzoylphenyl ester(22535-49-5)
• EPA Substance Registry System: 2-Propenoic acid,4-benzoylphenyl ester(22535-49-5)

Safety Data

• Hazardous Substances Data: 22535-49-5(Hazardous Substances Data)

Usage

Uses

Used in Sunscreen and Personal Care Products:
2-Propenoic acid, 4-benzoylphenyl ester is used as a UV filter for its ability to absorb and reflect the sun's rays, providing effective sun protection to the skin. It is commonly included in sunscreen formulations due to its efficacy in blocking harmful UV radiation.
Used in Cosmetic Industry:
In the cosmetic industry, benzophenone-4 is used as an ingredient in various personal care products to enhance their sun protection capabilities. Its inclusion in formulations helps to prevent skin damage caused by exposure to the sun, making it a valuable component in skincare products.
Despite the concerns regarding its safety, benzophenone-4 remains a widely used chemical in the cosmetic and personal care industry due to its effectiveness in providing sun protection. However, it is essential to continue researching and monitoring its potential risks to ensure the safety and well-being of consumers.

InChI:InChI=1/C16H12O3/c1-2-15(17)19-14-10-8-13(9-11-14)16(18)12-6-4-3-5-7-12/h2-11H,1H2

Synthetic route

acryloyl chloride (814-68-6) + 4-Hydroxybenzophenone (1137-42-4) → acrylic acid 4-benzoylphenyl ester (22535-49-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	80%
With triethylamine In dichloromethane; water Flow reactor;
With triethylamine; sodium hydroxide In water; ethyl acetate

3-chloro-propionic acid 4-benzoylphenyl ester (1159136-25-0) → acrylic acid 4-benzoylphenyl ester (22535-49-5)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate In acetone for 2h; Heating / reflux;

4-Hydroxybenzophenone (1137-42-4) + Methacryloyl chloride (920-46-7) → acrylic acid 4-benzoylphenyl ester (22535-49-5)

Conditions	Yield
In water; butanone

2-chloropropionyl chloride (625-36-5) + 4-Hydroxybenzophenone (1137-42-4) → acrylic acid 4-benzoylphenyl ester (22535-49-5)

Conditions	Yield
With triethylamine In dichloromethane; water Temperature; Flow reactor;

acrylic acid 4-benzoylphenyl ester (22535-49-5) + phenol (108-95-2) → 4-benzoylphenyl (E)-3-(2-hydroxyphenyl)acrylate

Conditions	Yield
With dipotassium peroxodisulfate; bis(acetylacetonato)palladium(II); silver(I) acetate; acetic acid In water at 60℃; Schlenk technique;	53%

acrylic acid 4-benzoylphenyl ester (22535-49-5) + 2,2'-iminobis[ethanol] (111-42-2) → 3-[bis(2-hydroxyethyl)amino]-propionic acid 4-benzoylphenyl ester (947609-92-9)

Conditions	Yield
In ethanol at 20 - 35℃; for 4.5h;

Upstream product

• 1159136-25-0 3-chloro-propionic acid 4-benzoylphenyl ester 
• 814-68-6 acryloyl chloride 
• 1137-42-4 4-Hydroxybenzophenone 
• 920-46-7 Methacryloyl chloride 
• 625-36-5 2-chloropropionyl chloride 

Relevant articles and documents

Photopolymerization and photophysical properties of amine linked benzophenone photoinitiator for free radical polymerization

Synthesis of amine linked type II photoinitiator (BPDEA) was achieved in high yields and photopolymerization of mono and multiacrylate monomers was performed with this photoinitiator in the absence of a coinitiator. BPDEA is more effective than benzophenone (BP) with the coinitiator (MDEA) system under inert atmosphere in photoinduced free radical polymerization of acrylates.

METHODS OF MAKING BENZOPHENONYL(ALK)ACRYLIC ESTERS AND SUBSTITUTED BENZOPHENONYL(ALK)ACRYLIC ESTERS IN FLOW REACTORS

A method of making a benzophenonyl (alk)acrylic ester comprising adding to a mixing chamber of a microflow reactor a benzophenone alcohol, a benzophenone alcohol or substituted benzophenone alcohol comprising at least one hydroxy moiety, one or more bases, a polar liquid, an (alk)acryloyl halide or 3-haloalkylcarboxyl halide, and an organic liquid that is immiscible with the polar liquid; and producing a product stream comprising one or more benzophenonyl (alk)acrylie esters and one or more salts of the one or more bases; wherein the product stream has an organic portion and a polar portion, the organic portion of the product stream comprising the benzophenonyl (alk)acrylic ester, unreacted benzophenone alcohol or substituted benzophenone alcohol, and organic byproducts in the product stream; and further wherein either (a) the organic liquid comprises a compound of Formula (I); or (b) the method further comprises adding a compound of Formula (I) to the product stream; or (c) the organic liquid comprises a compound of Formula (I) and the method further comprises adding a compound of Formula (I) to the product stream (I) wherein R1 is H or C1 to C4 alkyl; and R2 is C1 to C12 alkyl optionally interrupted by one or more O atoms.

METHODS OF MAKING (ALK)ACRYLIC ESTERS IN FLOW REACTORS

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

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.

Preparation method of copolymerizable photoinitiators

An intermediate for preparing (meth)acrylated photoinitiators according to Formula (I): wherein: R1 is selected from the group consisting of hydrogen and a methyl group; A represents a group comprising at least one photoinitiating moiety; L represents a n+o-valent linking group comprising at least one carbon atom; n and o each independently represent an integer from 1 to 4; p is equal to 0 or 1; X represents a group selected from the group consisting of Cl, Br, I and R2SO3; and R2 represents an optionally substituted group selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alkaryl group , an aralkyl group, an aryl group and a heteroaryl group. A method for the preparation of (meth)acrylated photoinitiators by β-elimination of HX from the intermediate according to Formula (I) is also disclosed.