131-53-3

Basic information

• Product Name: 2,2'-Dihydroxy-4-methoxybenzophenone
• Synonyms: (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanon;(2-Hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)methanone;(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-Methanone;2,2’-dihydroxy-4-methoxy-benzophenon;Advastab 47;advastab47;Benzophenone, 2,2'-dihydroxy-4-methoxy-;component of Solaquin
• CAS NO: 131-53-3
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• EINECS: 205-026-8
• Product Categories: Industrial/Fine Chemicals;Aromatic Benzophenones & Derivatives (substituted);Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Ketone
• Mol File: 131-53-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 73-75 °C(lit.)
• Boiling Point: 170-175 °C1 mm Hg(lit.)
• Flash Point: 146 °C
• Appearance: yellow powder
• Density: 1.2379 (rough estimate)
• Vapor Pressure: 0-0Pa at 20-25℃
• Refractive Index: 1.5389 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.11±0.35(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,3303
• CAS DataBase Reference: 2,2'-Dihydroxy-4-methoxybenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dihydroxy-4-methoxybenzophenone(131-53-3)
• EPA Substance Registry System: 2,2'-Dihydroxy-4-methoxybenzophenone(131-53-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DJ1049500
• Hazardous Substances Data: 131-53-3(Hazardous Substances Data)

Usage

Chemical Properties

yellow powder

Uses

Different sources of media describe the Uses of 131-53-3 differently. You can refer to the following data:
1. ultraviolet screen
2. benzophenone-8 (dioxybenzone) is an FDA-approved sunscreen chemical with uVA-absorption capabilities. It also can protect product degradation arising from uV-light exposure. It has an approved usage level of 3 percent in the united States.
3. Dioxybenzone is a compound used in sunscreen formulations to block out UVB and UVA harmful rays.

Preparation

preparation by condensation of salicylic acid and m-methoxyphenol.

General Description

Yellow powder.

Reactivity Profile

An alcohol and a ketone. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

Flash point data for 2,2'-Dihydroxy-4-methoxybenzophenone are not available. 2,2'-Dihydroxy-4-methoxybenzophenone is probably combustible.

Synthetic route

2,2',4-trimethoxybenzophenone (33077-87-1) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With hydrogen bromide; acetic acid at 110℃; Temperature;	85%

Benzophenone-3 (131-57-7) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; trifluoroacetic anhydride at 25 - 30℃; for 48h; regioselective reaction;	82%
With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; trifluoroacetic anhydride at 20℃; regioselective reaction;	82%
With dipotassium peroxodisulfate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; trifluoroacetic acid; trifluoroacetic anhydride at 80℃; for 20h; Sealed tube; regioselective reaction;	51%

2,2',4-Trihydroxybenzophenone (13087-18-8) + dimethyl sulfate (77-78-1) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With sulfolane; sodium carbonate; zinc(II) chloride In toluene at 45℃; for 2h; Solvent;	74.43%

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) + salicylaldehyde (90-02-8) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4) + 2,2'-dihydroxybenzophenone (835-11-0) + (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With dicarbonyl(acetylacotonato)rhodium(I); copper(II) acetate monohydrate; sodium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Schlenk technique; Inert atmosphere;	A 30% B 41% C 27%

2,2',4-trimethoxybenzophenone (33077-87-1) → 3-hydroxyxanthen-9-one (3722-51-8) + (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With pyridine hydrochloride

2-Methoxybenzoyl chloride (21615-34-9) + 1,3-Dimethoxybenzene (151-10-0) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With aluminium trichloride; chlorobenzene

O-methylresorcine (150-19-6) + salicylic acid (69-72-7) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

2-Methoxybenzoyl chloride (21615-34-9) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: pyridine hydrochloride View Scheme

1,3-Dimethoxybenzene (151-10-0) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: pyridine hydrochloride View Scheme

4-Methoxybenzophenone (611-94-9) → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; dipotassium peroxodisulfate / 4 h / 50 °C 2: silica gel / hexane; dichloromethane View Scheme

C18H10F6O6 → (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3)

Conditions	Yield
With silica gel In hexane; dichloromethane

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) + acetylenemagnesium bromide (4301-14-8) → C16H14O4

Conditions	Yield
In tetrahydrofuran at 0 - 70℃; for 3h; Grignard Reaction; Inert atmosphere;	80%

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 3-hydroxyxanthen-9-one (3722-51-8)

Conditions	Yield
With pyridine hydrochloride at 210 - 215℃; for 6h;	69%

mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)] (243643-58-5) + (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → C42H39Cl2O4P2Ru

Conditions	Yield
Stage #1: (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone With sodium hydroxide In methanol pH=9; Stage #2: mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)] In methanol	24%

phenylacetic acid (103-82-2) + methyl magnesium iodide (917-64-6) + (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → (Z,E)-4-(2-hydroxy-4-methoxyphenyl)-4-(2'-hydroxyphenyl)-2-methyl-3-phenylbut-3-en-2-ol (93097-67-7, 93444-33-8)

Conditions	Yield
Multistep reaction;

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 5-<(9-oxoxanthen-3-yl)oxy>valeric acid (161110-86-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → ethyl 5-<(9-oxoxanthen-3-yl)oxy>valerate (161110-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 5-(xanthen-3-yloxy)valeric acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. 4: 1.) NaBH4, NaOH, 2.) NaHCO3 / 1.) H2O, 50-55 deg C, 3 h, pH 8.0-8.5, 2.) 10 deg C, 1 h. View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 5-[9-(9H-Fluoren-9-ylmethoxycarbonylamino)-9H-xanthen-3-yloxy]-pentanoic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 69 percent / Py*HCl / 6 h / 210 - 215 °C 2: 86 percent / K2CO3 / acetone / 8 h / Heating 3: 1.) NaOH, 2.) HCl / 1.) EtOH, H2O, 25 deg C, 4 h, 2.) H2O, pH 3.5. 4: 1.) NaOH, Zn, 2.) TFA / 1.) aq. EtOH, reflux, 6 h, 2.) 1,2-dimethoxyethane, 25 deg C, 4 h. View Scheme

dichloro-acetic acid (79-43-6) + (2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 3-methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylic acid

Conditions	Yield
With potassium iodide; potassium carbonate In water; ethyl acetate; isopropyl alcohol

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 2,2',4-Trihydroxybenzophenone (13087-18-8)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃;
With boron tribromide In dichloromethane for 48h; Inert atmosphere;

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) + Methacryloyl chloride (920-46-7) → C22H20O6

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 12h;

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → (M,S)-7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; (5aR,10bS)-2-mesityl-5a,10b-dihydro-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazin-2-ium tetrafluoroborate / dichloromethane / 36 h / 24 °C / Molecular sieve; Inert atmosphere View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 3 h / 0 - 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; BF4(1-)*C21H22N3O(1+) / dichloromethane / 36 h / 24 °C / Molecular sieve; Inert atmosphere View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane 3: hydrogen; acetic acid / palladium / ethanol; hexane; water; ethyl acetate View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 3-Methoxy-12H-dibenzo-[d,g][1,3]dioxocin-6-carboxylic Acid (133704-96-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane 3: hydrogen; acetic acid / palladium / ethanol; hexane; water; ethyl acetate 4: sodium hydroxide / tetrahydrofuran; water View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → Methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylate (133704-94-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / water; ethyl acetate; isopropyl alcohol 2: methanol; hexane View Scheme

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone (131-53-3) → 2,2',4-Trihydroxybenzophenone (13087-18-8) + (2,4-dihydroxyphenyl)(2-hydroxy-4-methoxyphenyl)methanone (7392-62-3)

Conditions	Yield
With water; NADPH In aq. phosphate buffer at 37℃; for 2.5h; pH=7.4; Microbiological reaction;

Upstream product

• 33077-87-1 2,2',4-trimethoxybenzophenone 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 151-10-0 1,3-Dimethoxybenzene 
• 13087-18-8 2,2',4-Trihydroxybenzophenone 
• 77-78-1 dimethyl sulfate 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 90-02-8 salicylaldehyde 
• 131-57-7 Benzophenone-3 
• 611-94-9 4-Methoxybenzophenone 
• 150-19-6 O-methylresorcine 
• 69-72-7 salicylic acid 

Downstream Products

• 3722-51-8 3-hydroxyxanthen-9-one 
• 13087-18-8 2,2',4-Trihydroxybenzophenone 
• 7392-62-3 (2,4-dihydroxyphenyl)(2-hydroxy-4-methoxyphenyl)methanone 

Relevant articles and documents

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