90-96-0

Basic information

• Product Name: 4,4'-Dimethoxybenzophenone
• Synonyms: P,P'-DIMETHOXYBENZOPHENONE;LABOTEST-BB LT00160175;BIS(P-METHOXYPHENYL)-KETONE;4,4'-DIMETHOXYBENZOPHENONE;Benzophenone, 4,4'-dimethoxy-;Bis(4-anisyl) ketone;Bis(4-methoxyphenyl)methanone;Bis(p-anisyl) ketone
• CAS NO: 90-96-0
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27
• EINECS: 202-028-0
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;C15 to C38;Carbonyl Compounds;Ketones;Pyridines
• Mol File: 90-96-0.mol
• Article Data: 312

Chemical Properties

• Melting Point: 90-93 °C(lit.)
• Boiling Point: 200 °C17 mm Hg(lit.)
• Flash Point: 182 °C
• Appearance: Slightly beige to yellow/Powder
• Density: 1.1515 (rough estimate)
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: It is insoluble in water, soluble in ethanol.
• BRN: 1878026
• CAS DataBase Reference: 4,4'-Dimethoxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethoxybenzophenone(90-96-0)
• EPA Substance Registry System: 4,4'-Dimethoxybenzophenone(90-96-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 90-96-0(Hazardous Substances Data)

Usage

Description

4,4'-Dimethoxybenzophenone is a white to light yellow crystal powder that exhibits photoreactivity with 2-aminobenzimidazole. It is an ultraviolet absorbing additive in plastic products, making it a versatile compound with applications across various industries.

Uses

Used in Organic Synthesis:
4,4'-Dimethoxybenzophenone is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for the creation of a wide range of molecules, making it an essential component in the synthesis process.
Used in Pharmaceutical Industry:
4,4'-Dimethoxybenzophenone is used as a pharmaceutical intermediate, playing a crucial role in the development and production of various medications. Its properties enable it to be incorporated into drug molecules, contributing to their efficacy and safety.
Used in Agrochemicals:
In the agrochemical industry, 4,4'-Dimethoxybenzophenone is used as a raw material and intermediate for the synthesis of various agrochemical products. Its involvement in the production of these substances helps to ensure the development of effective and safe agricultural solutions.
Used in Dyestuff Industry:
4,4'-Dimethoxybenzophenone is also utilized in the dyestuff industry, where it serves as an important raw material and intermediate for the production of dyes and pigments. Its presence in these products contributes to their colorfastness and stability.
Overall, 4,4'-Dimethoxybenzophenone is a multifaceted compound with a diverse range of applications across various industries, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuff. Its unique properties and versatility make it an indispensable component in the development and production of numerous products.

Preparation

btained by photocatalytic oxidation of 4,4–′-dimethoxybenzhydrol (m.p. 69–71°) catalyzed by H3PW12O40/SiO2 in acetonitrile under oxygen atmosphere at r.t. for 1 h (90%).

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 3037, 1969 DOI: 10.1021/ja01039a036Tetrahedron Letters, 30, p. 1277, 1989 DOI: 10.1016/S0040-4039(00)72735-3

Purification Methods

Crystallise the ketone from absolute EtOH, aqueous EtOH or EtOH/AcOH. The 2,4-dinitrophenylhydrazone has m 199-200o. [Beilstein 8 H 317, 8 I 641, 8 II 355, 8 III 2649, 8 IV 2453.]

Upstream product

• 56-23-5 tetrachloromethane 
• 100-66-3 methoxybenzene 
• 75-44-5 phosgene 
• 57045-26-8 4-Ethoxycarbonyloxybenzoyl chloride 
• 728-87-0 4,4'-Dimethoxybenzhydrol 
• 76-03-9 trichloroacetic acid 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 509-14-8 tetranitromethane 
• 26957-36-8 2-methyl-1,1-(4,4-dimethoxydiphenyl)-1-propene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 124-38-9 carbon dioxide 
• 35861-33-7 4,4'-dimethoxybenzophenone radical 

Downstream Products

• 100-09-4 4-methoxybenzoic acid 
• 110663-65-5 1,1-bis-(4-methoxy-phenyl)-2-[2]pyridyl-ethanol 
• 4356-69-8 1,1-bis-(4-methoxyphenyl)ethylene 
• 500698-71-5 1,1-bis(4-methoxyphenyl)-2,2-diphenylethan-1-ol 
• 109723-66-2 4-hydroxy-4,4-bis-(4-methoxy-phenyl)-but-2-ynoic acid amide 
• 121816-51-1 1,1-bis-(4-methoxy-phenyl)-5,5-diphenyl-pentane-1,4-dien-3-one 
• 18499-68-8 1,4-bis-[3-hydroxy-3,3-bis-(4-methoxy-phenyl)-prop-1-ynyl]-benzene 
• 18499-71-3 9,10-bis-[3-hydroxy-3,3-bis-(4-methoxy-phenyl)-prop-1-ynyl]-anthracene 
• 31067-02-4 1,1-Bis(p-methoxyphenyl)ethan-1-ol 
• 4663-13-2 1,1-bis(4-methoxyphenyl)propene 
• 26957-36-8 2-methyl-1,1-(4,4-dimethoxydiphenyl)-1-propene 
• 26642-57-9 1,1-bis(4-methoxyphenyl)-2-phenylethene 
• 20114-55-0 4,4'-dimethoxybenzophenone hydrazone 
• 611-99-4 4,4'-Dihydroxybenzophenone 

Relevant articles and documents

Chemical capture of an unprecedented oxatetramethyleneethane radical cation with a through-space electronic coupling

A photoinduced electron-transfer reaction of 2,2-dianisyl-4-isopropylidene- 3,3-dimethylcyclobutanone (5) in acetonitrile containing molecular oxygen or water gave 4,4′-dimethoxybenzophenone (7) and 2,2-dianisyl-4- isopropylidene-5,5-dimethylhydrofuran-3-one (8), demonstrating the chemical capture of an unprecedented oxatetramethyleneethane-type radical cation intermediate (6?+). A density functional theory calculation suggests through-space electronic coupling between the tetramethylallyl and joined dianisylmethyl carbonyl subunits in 6?+.

Preparation, redox properties, and x-ray structures of electrochromic 11,11,12,12-tetraarylanthraquinodimethane and its bianthraquinodimethane analogue: Drastic geometrical changes upon interconversion with dicationic dyes

Tetrakis(4-methoxyphenyl)anthraquinodimethane 1(b) with a bent geometry undergoes reversible redox interconversion with twisted dication 1(t) 2+ exhibiting a vivid change in color (electrochromism) accompanied by a drastic structural change. Electrochemical oxidation of bianthraquinodimethane 2(b) with a doubly bent structure to bianthrylidene-type twisted dication 2(t)2+ proceeded smoothly, whereas the reverse conversion was less effective because 2(t)2 generated upon reduction of 2(t)2+ is a long-lived species to undergo side reactions.

Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide

A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).

Method for preparing aldehyde ketone compound through olefin oxidation

The invention provides a method for preparing an aldehyde ketone compound by olefin oxidation, which relates to an olefin oxidative cracking reaction in which oxygen participates. The method comprises the following specific steps: in the presence of a solvent and an oxidant, carrying out oxidative cracking on an olefin raw material to obtain a corresponding aldehyde ketone product. Compared with the traditional method, the method does not need to add any catalyst or ligand, does not need to use high-pressure oxygen, has the advantages of simple and mild reaction conditions, environment friendliness, low cost, high atom economy and the like, is wide in substrate application range and high in yield, and has a wide application prospect in the aspects of synthesis of aldehyde ketone medical intermediates and chemical raw materials.

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.