2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE Property

Melting point:

99-102°C

Boiling point:

345.09°C (rough estimate)

Density 

1.1515 (rough estimate)

refractive index 

1.5570 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly, Heated), Methanol (Slightly, Heated)

pka

7.35±0.35(Predicted)

form 

Solid

color 

Pale Yellow to Light Yellow

Merck 

14,6167

BRN 

1972646

LogP

4.100 (est)

CAS DataBase Reference

1641-17-4(CAS DataBase Reference)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazardous Substances Data

1641-17-4(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P501Dispose of contents/container to..…

2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE Chemical Properties,Usage,Production

Originator

Uvistat-L,Ward Blenkinsop,UK,1960

Uses

2-Hydroxy-4-methoxy-4'-methyl-benzophenone is an UV absorbing agent in sunscreen cosmetic creams, lotions, lipstieks, sun oils, etc.

Preparation

Preparation by Friedel–Crafts acylation of m-methoxy-phenol with p-toluoyl chloride,
in the presence of boron trichloride in benzene first at ?10°, then at reflux for 10 h under nitrogen (80%)
in the presence of titanium tetrachloride in benzene first at ?10°, then at reflux for 14 h under nitrogen (73%) or in chlorobenzene for 1 h at 120° (79%).

Definition

ChEBI: Mexenone is a member of benzophenones.

Manufacturing Process

p-Toluoyl chloride is the starting material. To this is added chlorobenzene and 1,3-dimethoxybenzene. The reaction mixture is cooled to 12°C in an ice bath and aluminum chloride is added gradually, keeping the reaction below 30°C. The reaction is then gradually heated to 115°C with the evolution of hydrogen chloride gas. As the temperature increases, the reaction mixture becomes thicker. At 105°C, dimethyl formamide is added slowly. The reaction is heated at 115°C for a short time and is then poured into concentrated hydrochloric acid. The reaction mixture pours very easily and very cleanly. The acid mixture is heated with steam to dissolve all the material which had not hydrolyzed and the mixture is filtered. The red chlorobenzene layer is separated and washed twice with hot water.
To the chlorobenzene solution is then added sodium hydroxide dissolved in water and the chlorobenzene is removed by a steam distillation. After all of the chlorobenzene is removed, the precipitate which forms during the distillation is removed by filtration and discarded. The solution is cooled and acidified with hydrochloric acid, precipitating a tan solid. This is removed by filtration and washed acid-free. It is then treated with sodium bicarbonate solution to remove any acid present and is then washed with water to remove all traces of bicarbonate. After drying approximately a 75% yield of mexenone is obtained.

Therapeutic Function

Sunscreen agent

Contact allergens

BZP-10 is exceptionally positive in ketoprofen-photosensitive patients.