1641-17-4

Basic information

• Product Name: 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE
• Synonyms: 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE;LABOTEST-BB LT00455260;MEXENONE;''MEXENONE'';BENZOPHENONE-10;benzophenone-10,2-hydroxy-4-methoxy-4’-methylbenzophenone;(2-Hydroxy-4-methoxyphenyl)(4-methylphenyl)methanone;HYDROXYMETHOXYMETHYLBENZOPHENONE
• CAS NO: 1641-17-4
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27
• EINECS: 216-688-2
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);UVISTAT
• Mol File: 1641-17-4.mol

Chemical Properties

• Melting Point: 99-102°C
• Boiling Point: 345.09°C (rough estimate)
• Flash Point: 150.2 ºC
• Appearance: White or yellow powder
• Density: 1.1515 (rough estimate)
• Vapor Pressure: 5.65E-07mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: 7.35±0.35(Predicted)
• Merck: 14,6167
• BRN: 1972646
• CAS DataBase Reference: 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE(1641-17-4)
• EPA Substance Registry System: 2-HYDROXY-4-METHOXY-4'-METHYLBENZOPHENONE(1641-17-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 1641-17-4(Hazardous Substances Data)

Usage

Originator

Uvistat-L,Ward Blenkinsop,UK,1960

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%).

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.

InChI:InChI=1/C15H14O3/c1-10-3-5-11(6-4-10)15(17)13-8-7-12(18-2)9-14(13)16/h3-9,16H,1-2H3

Upstream product

• 150-19-6 O-methylresorcine 
• 874-60-2 4-methyl-benzoyl chloride 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 42059-56-3 7-methoxy-3-formylchromone 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 151-10-0 1,3-Dimethoxybenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 329235-36-1 2-formyl-5-methoxyphenyl 4-methylbenzenesulfonate 

Relevant articles and documents

Eco-friendly organocatalyst- And reagent-controlled selective construction of diverse and multifunctionalized 2-hydroxybenzophenone frameworks for potent UV-A/B filters by cascade benzannulation

The organocatalyst- and reagent-controlled highly selective synthesis of diversely functionalized novel 2-hydroxybenzophenone frameworks, such as 2-hydroxy-3′-formylbenzophenones, 7-(2′-hydroxybenzoyl)-2-naphthaldehydes, and 2-hydroxybenzophenones, under green conditions, for the development of potent UV-A/B filters is described. The organocatalyzed benzannulation reactions proceed individually via [3 + 3] cycloaddition for the synthesis of 2-hydroxy-3′-formylbenzophenones and [4 + 2] cycloaddition for 2-hydroxybenzophenones. With this methodology, an unprecedented double benzannulation allows one-pot construction of diverse 7-(2′-hydroxybenzoyl)-2-naphthaldehydes via [3 + 3 + 4] cycloaddition. This protocol features a broad substrate scope, high functional-group tolerance, and operational simplicity in an environmentally benign green solvent. The synthesized compounds are successfully utilized for further transformations and well characterized as potent UV-A/B filters.

Operationally Simple and Selective One-Pot Synthesis of Hydroxyphenones: A Facile Access to SNARF Dyes

High selectivity is observed during a Friedel-Crafts acylation/demethylation cascade. In contrast to this cascade, oxygen-containing acylating reagents do not undergo the demethylation step. By the methodology elaborated here, an access is provided to important intermediates for the total synthesis of seminaphthorhodafluor (SNARF) dyes.

Synthesis of 2-acylphenol and flavene derivatives from the ruthenium-catalyzed oxidative c-h acylation of phenols with aldehydes

The cationic ruthenium hydride complex [(C6H6)(PCy3)(CO)RuH]+BF4- has been found to be an effective catalyst for the oxidative C-H coupling reaction of phenols with aldehydes to give 2-acylphenol compounds. The coupling of phenols with α,β-unsaturated aldehydes selectively gives the flavene derivatives. The catalytic method mediates direct oxidative C-H coupling of phenol and aldehyde substrates without using any metal oxidants or forming wasteful byproducts. A cationic ruthenium hydride complex catalyzes the oxidative C-H coupling of phenols with aldehydes to form 2-acylphenol and flavene derivatives.

Cosmetic compositions

Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.

A composition for lightening skin and hair

Suggested is a composition comprising (a) sclareolide and (b1) at least one tyrosinase inhibitor; and/or (b2) at least one sun protection factor; and/or (b3) at least one anti-oxidants; and/or (b4) at least one anti-inflammatory agent; and/or (b5) at least one desquamating agent.

A concise approach to the preparation of 2-hydroxydiarylketones by an intramolecular acyl radical ipso substitution

Substituted 2-hydroxydiarylketones have been simply prepared using an intramolecular acyl radical [1,6] ipso substitution reaction. (C) 2000 Elsevier Science Ltd.

Light-stable screening cosmetic composition containing bixin combined with a lipid-soluble UV filter and its use for protecting the human epidermis against ultra-violet radiation

The invention relates to a light-stable cosmetic composition for protecting the human epidermis against UV radiation, containing at least 0.0025% by weight of bixin combined with at least 1% by weight of one or more lipid-soluble agents screening UV radiation, chosen from 3-benzylidene-dl-camphor, its derivatives and benzophenone derivatives, in a cosmetically acceptable vehicle comprising at least one fatty phase. The bixin takes the form of an oily extract of annatto containing at least 0.1% by weight of bixin.

BORON TRICHLORIDE CATALYZED ORTHO CARBONYLATION OF PHENOLS: SYNTHESIS OF 2-HYDROXY-ARYL-CARBOXYAMIDES AND -KETONES.

In the presence of equimolar quantity of BCl3, phenols 1 react with isocyanates and acyl chlorides to give, usually with good-excellent yields, 2-hydroxy-aryl-carboxy-amides 2 and 2-hydroxy-aryl-ketones 3 respectively.A distinctive behaviour of BCl3 in comparison with other Lewis acids is observed.

Infrared study of polysubstitution effects in benzophenones and acetophenones: contribution of inter and intracycle interaction mechanisms

The carbonyl stretching frequencies of substituted 2-Me, 2,6-diMe, 2-MeO benzophenones and 2-Me, 2-MeO acetophenones have been measured in diluted CCl4 solutions.Two interaction mechanisms are observed.In X, Y substituted benzophenones with X on the same cycle as the ortho group and Y on the other cycle, it is shown that for X=Y, the effect of Y is greater than that of X except for very strong electron-releasing substituents.In this last case, the observed enhancement is attributed to the joint effects of intercycle interactions excercised on X and Y and of intracycle interaction on X.These results are corroborated by the study of substituted acetophenones in which only the intracycle mechanism can play a role.

Method of treating inflammation

A method of treating inflammation and inhibiting prostaglandin synthesis employing 2-hydroxybenzophenone and substituted 2-hydroxybenzophenones.