10425-11-3

Basic information

• Product Name: 3,4-Dihydroxybenzophenone
• Synonyms: 3,4-DIHYDROXY-DIPHENYL KETONE;3,4-DIHYDROXYBENZOPHENONE;(3,4-DIHYDROXYPHENYL)(PHENYL)METHANONE;3,4-Dihydroxybenzophenone(Bp-15);3,4-dihydroxybnezophenone;3,4-dihydroxy benzophonone;3,4-DIHYDROXYBENZOPHENONE, 98%%;Methanone, (3,4-dihydroxyphenyl)phenyl-
• CAS NO: 10425-11-3
• Molecular Formula: C₁₃H₁₀O₃
• Molecular Weight: 214.22
• EINECS: 1312995-182-4
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);C13 to C14;Carbonyl Compounds;Ketones
• Mol File: 10425-11-3.mol

Chemical Properties

• Melting Point: 144-148 °C(lit.)
• Boiling Point: 314.35°C (rough estimate)
• Flash Point: 230.3 °C
• Appearance: White to off-white powder
• Density: 1.1956 (rough estimate)
• Vapor Pressure: 3.93E-08mmHg at 25°C
• Refractive Index: 1.5090 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 8.02±0.18(Predicted)
• CAS DataBase Reference: 3,4-Dihydroxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydroxybenzophenone(10425-11-3)
• EPA Substance Registry System: 3,4-Dihydroxybenzophenone(10425-11-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 10425-11-3(Hazardous Substances Data)

Usage

Chemical Properties

cream crystalline powder

Preparation

Preparation by Fries rearrangement of pyrocatechol dibenzoate, in the presence of aluminium chloride in nitrobenzene ? at 100° for 4 h (quantitative yield) or heated on a steam bath for 6 h ]; ? in the presence of Nafion-XR, a H+-form ion exchange resin, at 175° for 4 h under nitrogen (38%).

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 2601, 1994 DOI: 10.1016/S0040-4039(00)77182-6

InChI:InChI=1/C13H10O3/c14-11-7-6-10(8-12(11)15)13(16)9-4-2-1-3-5-9/h1-8,14-15H

Upstream product

• 643-94-7 o-phenylene dibenzoate 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 71-43-2 benzene 
• 120-80-9 benzene-1,2-diol 
• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 
• 119-61-9 benzophenone 
• 13020-57-0 3-hydroxybenzophenone 
• 147644-07-3 (3,4-dihydro-2H-benzo[b]1,4-dioxepin-7-yl)(phenyl)methanone 
• 65-85-0 benzoic acid 
• 1137-42-4 4-Hydroxybenzophenone 
• 93637-87-7 2,3-dihydro-1,4-benzodioxin-6-yl(phenyl)methanone 
• 110851-16-6 2,9,11,12,13-Pentaoxa-tricyclo[8.2.1.0^3,8]trideca-3,5,7-triene 
• 110851-22-4 1,10-Dimethyl-2,9,11,12,13-pentaoxa-tricyclo[8.2.1.0^3,8]trideca-3,5,7-triene 

Downstream Products

• 786705-95-1 3,4-bis-allyloxy-benzophenone 
• 147644-07-3 (3,4-dihydro-2H-benzo[b]1,4-dioxepin-7-yl)(phenyl)methanone 
• 412028-14-9 phenyl([1,1';2',1]terphenyl-4'-yl)methanone 
• 1360171-40-9 [4'-methyl-6-(p-tolylethynyl)biphenyl-3-yl]phenylmethanone 
• 1360171-39-6 3-trifluorosulfonyloxy-4-methylphenylaceylenebenzophenone 
• 1360171-38-5 [3,4-bis(m-tolylethynyl)phenyl]phenylmethanone 
• 1360171-36-3 {3,4-bis[(4-fluorophenyl)ethynyl]phenyl}phenylmethanone 
• 1360171-34-1 [3,4-bis(p-tolylethynyl)phenyl]phenylmethanone 
• 1360171-32-9 {3,4-bis[(3-methoxyphenyl)ethynyl]phenyl}phenylmethanone 
• 1360171-30-7 [3,4-bis(phenylethynyl)phenyl]phenylmethanone 
• 1360171-28-3 {3,4-bis[(4-tert-butylphenyl)ethynyl]phenyl}phenylmethanone 
• 1233541-94-0 4-benzoyl-4'-tert-butylbiphenyl-2-yl trifluoromethanesulfonate 
• 1233541-93-9 4-benzoyl-3',4',5'-trimethoxybiphenyl-2-yl trifluoromethanesulfonate 
• 1233541-92-8 4-benzoyl-4'-methylbiphenyl-2-yl trifluoromethanesulfonate 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

An efficient strategy for protecting dihydroxyl groups of catechols

A novel strategy for protecting dihydroxyl groups of catechols has been developed. Base-mediated cyclizations of catechols with 1,3-dibromopropane provided the corresponding benzo[b]1,4-dioxepans, and herefrom the protecting group was easily cleaved by aluminum chloride. The preparation of the antibacterial and antifungal agent 4-(2-aminothiazol-4-yl)benzene-1,2-diol from catechol reliably verified its availability amenable to various harsh reaction conditions. Georg Thieme Verlag Stuttgart - New York.

Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation

Zn powder is found to catalyze the Friedel-Crafts acylation of aromatic compounds with acyl halides efficiently under microwave irradiation in solvent-free conditions. Activated substrates undergo acylation predominantly at the para-position. The Zn powder can be re-used up to six times after simple washing with diethyl ether and dilute HCl.

HZSM-5 catalysed regiospecific benzoylation of activated aromatic compounds

HZSM-5 has been shown to display a remarkable reaction selectivity in the liquid-phase benzoylation of activated arenes to benzophenones in high yields.

Photolysis of the Ozonide Derived from 1,4-Benzodioxins. Synthesis of Labile o-Benzoquinones

By the photolysis of the ozonide derived from 1,4-benzodioxins, o-benzoquinones were obtained in moderate yields independent of the stability of o-benzoquinones and of the substituent groups, except the nitro group.Through the mechanistic studies, it was indicated that o-benzoquinones were formed through a radical decomposition pathway, while catechols were formed through an ionic decomposition pathway induced by acidic impurities.

LATINONE, A PHENANTHRENE-1,4-QUINONE FROM DALBERGIA LATIFOLIA

Latinone, a substituted phenanthrene-1,4-quinone was isolated from Dalbergia latifolia.The structure was assigned from spectroscopic measurements and a synthesis was carried out using a Diels-Alder reaction to form the ring structure.Key Word Index- Dalbergia latifolia; Leguminosae; latinone; quinone; phenanthrene-1,4-quinone.

Reactions of Benzoyl Peroxide with 4-Hydroxybiphenyl, 4-Hydroxybenzophenone and 2-Hydroxy-5-methylbenzophenone

Interaction of benzoyl peroxide with 4-hydroxybiphenyl (I) and 4-hydroxybenzophenone (IV) leads to ortho-benzoyloxylation, giving 3-benzoyloxylated derivatives.A similar reaction with 2-hydroxy-5-methylbenzophenone (VII) results in dimerisation involving the side methyl group.The phenyl and benzoyl groups, thus do not inhibit benzoyloxylation.The formation of the dimer (VIII) from the ketone (VII) shows that it is difficult to achieve ortho-benzoyloxylation with chelated hydroxyl group.