5173-27-3

Usage

Molecular weight

228.29 g/mol

Appearance

Colorless to white crystalline solid

Solubility

Soluble in organic solvents like ethanol, acetone, and diethyl ether

Melting point

155-156°C

Boiling point

Decomposes before boiling

Density

1.194 g/cm3

Structure

Consists of two phenol groups connected by a carbon-carbon bond

Production

Synthesized from acetone and phenol through a condensation reaction

Applications

Widely used in the production of plastics (polycarbonate) and epoxy resins

Health concerns

Mimics estrogen, linked to reproductive disorders, obesity, and cardiovascular diseases

Presence

Commonly found in food and beverage containers, dental sealants, and thermal receipt papers

Regulations

Many countries have implemented restrictions or bans on the use of BPA in certain products due to potential health risks

Alternatives

Some manufacturers have developed BPA-free alternatives for use in consumer goods

InChI:InChI=1/C14H14O4/c15-11-5-1-9(2-6-11)13(17)14(18)10-3-7-12(16)8-4-10/h1-8,13-18H

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 33288-79-8 4,4'-dihydroxybenzil 
• 556-56-9 allyl iodid 
• 131543-46-9 Glyoxal 
• 108-95-2 phenol 
• 100-52-7 benzaldehyde 

Downstream Products

• 7727-33-5 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane 
• 6052-84-2 4,4'-ethylenediphenol 
• 156176-93-1 3,4,6,7-tetrahydro-3,3,6,6-tetramethyl-9-(4-hydroxyphenyl)acridine-1,8(2H,5H,9H,10H)-dione 
• 123629-41-4 ethyl 4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1752-94-9 4-(4,5-diphenyl-1H-imidazol-2-yl)phenol 

Relevant academic research and scientific papers

BENZOXAZINE-BASED MIXTURE AND USE THEREOF

The present invention relates to a benzoxazine-based mixture and a use thereof and, more specifically, to a benzoxazine-based mixture and a use of a cured product in which the benzoxazine-based mixture is cured, wherein the benzoxazine-based mixture has high dielectric characteristics, heat resistant characteristics, and flame-retardant characteristics by comprising a benzoxazine ring in a molecular structure, and thus can be applied to a sealing material, a molding material, a template material, an adhesive, a material for an electric insulation paint, and the like, which are used for a copper clad laminate or an electronic part, used in a printed circuit board.

Biginelli reaction of vicinal diols: A new route for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives

Background: 3,4-Dihydropyrimidin-2(1H)-one derivatives are an important class of nitrogen heterocycles. These compounds present a wide range of biological activities viz antibacterial, antifungal, and antidiabetic. Although many synthetic methods are available in the literature for the synthesis of these molecules, many of these methods have their own limitations such as use of excess of expensive catalyst and poor yields. Methods: The synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives is developed through the reaction of 1,2-diols, ethyl acetoacetate and urea in the presence of lead tetraacetate in dry ethanol under reflux conditions. Results: A series of 3,4-dihydropyrimidin-2(1H)-one derivatives were synthesized in good yields (82-95%) under reflux for 2-3.5 hours in ethanol solvent. The structural assignments of these compounds were made on the basis of elemental analysis and spectroscopic data. Conclusion: This protocol is an alternative to existing procedure for the synthesis of Biginelli compounds. The present methodology reduces the number of steps in total synthesis.

A convenient synthesis of unsymmetrical pinacols by coupling of structurally similar aromatic aldehydes mediated by low-valent titanium

The one-pot, selective cross pinacol-type couplings between two structurally similar aromatic aldehydes promoted by low-valent titanium generated unsymmetrical pinacols in moderate to good isolated yields in an erythrolthreo ratio of up to 91:9. This synt

METHOD OF PRODUCING DIOL, POLYDIOL, SECONDARY ALCOHOL OR DIKETONE COMPOUND

The invention is a process of using, as a reducing agent, a 12CaO·7Al2O3 electride containing electrons in a number of 1019 cm-3 or more and 2.3 × 1021 cm-3 or less in its cages to subject a carbonyl compound to reductive coupling in a solvent, thereby synthesizing a diol or polydiol. The invention is also a process of reducing a ketone compound in a solvent, thereby synthesizing a secondary alcohol or diketone compound. According to the process of the invention, it is possible to synthesize a diol or polydiol, or a secondary alcohol or diketone compound through simple operations in a short period without using an expensive and harmful metal hydride or metal salt nor limiting the atmosphere for the synthesis to an inert gas atmosphere as in conventional processes.

Zirconocene dichloride-catalyzed pinacol coupling of aromatic aldehydes and ketones

The reductive coupling of aromatic aldehydes and ketones has been achieved using a catalytic amount of zirconocene dichloride in the presence of magnesium metal and chlorotrimethylsilane in THF at room temperature to afford the corresponding 1,2-diols in good yields and diastereoselectivity. Copyright Taylor & Francis Group, LLC.

METHOD FOR PRODUCING TETRAKISPHENOLETHANE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing a tetrakisphenolethane compound represented by formula (3) in a high yield and with a high production efficiency. SOLUTION: The method for producing a tetrakisphenol compound represented by formula (3) (wherein R1, R3, R4, and R6 are each hydrogen, a 1-20C alkyl group, a halogen or the like; R2 and R5 are each hydrogen, a 1-20C alkyl group, a 1-20C alkoxyalkyl group or the like; and R9 and R10 are each hydrogen, a 1-20C alkyl group, a halogen, a 1-20C alkoxy group, a 1-20C haloalkoxy group or the like) comprises reacting a dioxyethane compound represented by formula (1) (wherein R1, R2, R3, R4, R5, and R6 are the same as defined above; and R7 and R8 are each hydrogen, a 1-20C alkyl group, a 1-20C alkoxyalkyl group or the like ) with a phenol represented by formula (2) (wherein R9 and R10 are the same as defined above) in the presence of an acid catalyst. COPYRIGHT: (C)2006,JPOandNCIPI

Reactions of azulenes with 1,2-diaryl-1,2-ethanediols in methanol in the presence of hydrochloric acid: Comparative studies on products, crystal structures, and spectroscopic and electrochemical properties

Although reaction of guaiazulene (1a) with 1,2-diphenyl-1,2-ethanediol (2a) in methanol in the presence of hydrochloric acid at 60°C for 3 h under aerobic conditions gives no product, reaction of 1a with 1,2-bis(4- methoxyphenyl)-1,2-ethanediol (2b) under the same reaction conditions as 2a gives a new ethylene derivative, 2-(3-guaiazulenyl)-1,1-bis(4-methoxyphenyl) ethylene (3), in 97% yield. Similarly, reaction of methyl azulene-1-carboxylate (1b) with 2b under the same reaction conditions as 1a gives no product; however, reactions of 1-chloroazulene (1c) and the parent azulene (1d) with 2b under the same reaction conditions as 1a give 2-[3-(1-chloroazulenyl)]-1,1-bis(4- methoxyphenyl)ethylene (4) (81% yield) and 2-azulenyl-1,1-bis(4-methoxyphenyl) ethylene (5) (15% yield), respectively. Along with the above reactions, reactions of 1a with 1,2-bis(4-hydroxyphenyl)-1,2-ethanediol (2c) and 1-[4-(dimethylamino)phenyl]-2-phenyl-1,2-ethanediol (2d) under the same reaction conditions as 2b give 2-(3-guaiazulenyl)-1,1-bis(4-hydroxyphenyl)ethylene (6) (73% yield) and (Z)-2-[4-(dimethylamino)phenyl]-1-(3-guaiazulenyl)-1- phenylethylene (7) (17% yield), respectively. Comparative studies of the above reaction products and their yields, crystal structures, spectroscopic and electrochemical properties are reported and, further, a plausible reaction pathway for the formation of the products 3-7 is described.

Synthesis of pinacols through electrochemical reduction of carbonyl compounds at platinum cathode in non-aqueous weakly acidic medium

The electrochemical reduction of p-methylacetophenone, m-nitrobenzaldehyde p-dimethylaminobenzaldehyde and p-hydroxybenzaldehyde was carried out at controlled potential in weakly acidic medium (phenol, pKa = 9.98) for the purpose of investigating this type of reduction as a possible synthetic procedure for the preparation of 1,2-diol (or pinacol). The products formed during electrolysis at constant cathode potential are reported here.

Magnesium-mediated carbon-carbon bond formation in aqueous media: Barbier-Grignard allylation and pinacol coupling of aldehydes

Magnesium-mediated Barbier-Grignard type alkylation of aldehydes with alkyl halides was studied in aqueous media. The reaction of aromatic aldehydes with allyl halides is highly effective with either THF or water as the reaction solvent but poor in a mixture of THF/water. It was found that the magnesium-mediated allylation of aldehydes with allyl bromide and iodide proceeds effectively in aqueous 0.1 N HCl or 0.1 N NH4Cl. Aromatic aldehydes reacted chemoselectively in the presence of aliphatic aldehydes. An exclusive selectivity was also observed when both aliphatic and aromatic aldehyde functionalities are present in the same molecule. In the absence of allyl halides, aldehydes and ketones reacted with magnesium in aqueous 0.1 N NH4Cl to form the corresponding pinacol coupling products in high yields. The effectiveness of the pinacol reaction was strongly influenced by the steric environment surrounding the carbonyl group. Aliphatic aldehydes and simple alkyl halides appear inert under the reaction conditions for either alkylation or the pinacol coupling reaction.