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
• Article Data: 5

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

General Description

2-Propenoic acid, 4-benzoylphenyl ester, also known as benzophenone-4, is a chemical compound commonly used in the production of sunscreens and personal care products. It is a UV filter that helps to protect the skin from the harmful effects of UV radiation by absorbing and reflecting the sun's rays. Benzophenone-4 is considered to be an effective ingredient for sun protection and is commonly included in sunscreen formulations. However, there have been concerns raised regarding its safety and potential risk of skin irritation or allergic reactions in some individuals. Despite this, it remains a widely used chemical in the cosmetic and personal care industry.

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 (ALK)ACRYLIC ESTERS IN FLOW REACTORS

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

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.