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2,2'-Dihydroxy-4-methoxybenzophenone, also known as benzophenone-8 (dioxybenzone), is a yellow powder with chemical properties that make it an effective compound for various applications, particularly in the field of sunscreen formulations.

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  • 131-53-3 Structure
  • Basic information

    1. Product Name: 2,2'-Dihydroxy-4-methoxybenzophenone
    2. 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
    3. CAS NO:131-53-3
    4. Molecular Formula: C14H12O4
    5. Molecular Weight: 244.24
    6. EINECS: 205-026-8
    7. Product Categories: Industrial/Fine Chemicals;Aromatic Benzophenones & Derivatives (substituted);Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Ketone
    8. Mol File: 131-53-3.mol
  • Chemical Properties

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

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS: DJ1049500
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 131-53-3(Hazardous Substances Data)

131-53-3 Usage

Uses

Used in Sunscreen Industry:
2,2'-Dihydroxy-4-methoxybenzophenone is used as an ultraviolet (UV) screen for its ability to absorb both UVA and UVB harmful rays, providing protection against the damaging effects of sunlight. It is an FDA-approved sunscreen chemical with an approved usage level of 3 percent in the United States.
Used in Cosmetics Industry:
2,2'-Dihydroxy-4-methoxybenzophenone is also used as a protective agent in cosmetics to prevent product degradation arising from UV-light exposure, ensuring the stability and longevity of the products.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2,2'-Dihydroxy-4-methoxybenzophenone may also have potential applications in the pharmaceutical industry, possibly as an intermediate in the synthesis of other compounds or for its light-protective properties in certain medications.

Preparation

preparation by condensation of salicylic acid and m-methoxyphenol.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 131-53-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 1 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 131-53:
(5*1)+(4*3)+(3*1)+(2*5)+(1*3)=33
33 % 10 = 3
So 131-53-3 is a valid CAS Registry Number.

131-53-3 Well-known Company Product Price

  • Brand
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  • CAS number
  • Packaging
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  • Sigma-Aldrich

  • (92841)  Dioxybenzone  analytical standard

  • 131-53-3

  • 92841-100MG

  • 1,437.93CNY

  • Detail
  • USP

  • (1214004)  Dioxybenzone  United States Pharmacopeia (USP) Reference Standard

  • 131-53-3

  • 1214004-150MG

  • 4,662.45CNY

  • Detail
  • Aldrich

  • (323578)  2,2′-Dihydroxy-4-methoxybenzophenone  98%

  • 131-53-3

  • 323578-25G

  • 733.59CNY

  • Detail
  • Aldrich

  • (323578)  2,2′-Dihydroxy-4-methoxybenzophenone  98%

  • 131-53-3

  • 323578-100G

  • 2,461.68CNY

  • Detail

131-53-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,2'-Dihydroxy-4-methoxybenzophenone

1.2 Other means of identification

Product number -
Other names dioxybenzone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:131-53-3 SDS

131-53-3Synthetic route

2,2',4-trimethoxybenzophenone
33077-87-1

2,2',4-trimethoxybenzophenone

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 110℃; Temperature;85%
Benzophenone-3
131-57-7

Benzophenone-3

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
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

2,2',4-Trihydroxybenzophenone

dimethyl sulfate
77-78-1

dimethyl sulfate

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
With sulfolane; sodium carbonate; zinc(II) chloride In toluene at 45℃; for 2h; Solvent;74.43%
2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

salicylaldehyde
90-02-8

salicylaldehyde

A

bis(2-hydroxy-4-methoxyphenyl)-methanone
131-54-4

bis(2-hydroxy-4-methoxyphenyl)-methanone

B

2,2'-dihydroxybenzophenone
835-11-0

2,2'-dihydroxybenzophenone

C

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
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

2,2',4-trimethoxybenzophenone

A

3-hydroxyxanthen-9-one
3722-51-8

3-hydroxyxanthen-9-one

B

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
With pyridine hydrochloride
2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
With aluminium trichloride; chlorobenzene
O-methylresorcine
150-19-6

O-methylresorcine

salicylic acid
69-72-7

salicylic acid

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

2-Methoxybenzoyl chloride
21615-34-9

2-Methoxybenzoyl chloride

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: pyridine hydrochloride
View Scheme
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: pyridine hydrochloride
View Scheme
4-Methoxybenzophenone
611-94-9

4-Methoxybenzophenone

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium diacetate; dipotassium peroxodisulfate / 4 h / 50 °C
2: silica gel / hexane; dichloromethane
View Scheme
C18H10F6O6

C18H10F6O6

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Conditions
ConditionsYield
With silica gel In hexane; dichloromethane
(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone
131-53-3

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

acetylenemagnesium bromide
4301-14-8

acetylenemagnesium bromide

C16H14O4

C16H14O4

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 70℃; for 3h; Grignard Reaction; Inert atmosphere;80%
(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone
131-53-3

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

3-hydroxyxanthen-9-one
3722-51-8

3-hydroxyxanthen-9-one

Conditions
ConditionsYield
With pyridine hydrochloride at 210 - 215℃; for 6h;69%
mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)]
243643-58-5

mer-[(1,4-bis(diphenylphosphino)butane)aquatrichlororuthenium(III)]

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

C42H39Cl2O4P2Ru

C42H39Cl2O4P2Ru

Conditions
ConditionsYield
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

phenylacetic acid

methyl magnesium iodide
917-64-6

methyl magnesium iodide

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

(Z,E)-4-(2-hydroxy-4-methoxyphenyl)-4-(2'-hydroxyphenyl)-2-methyl-3-phenylbut-3-en-2-ol
93097-67-7, 93444-33-8

(Z,E)-4-(2-hydroxy-4-methoxyphenyl)-4-(2'-hydroxyphenyl)-2-methyl-3-phenylbut-3-en-2-ol

Conditions
ConditionsYield
Multistep reaction;
(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone
131-53-3

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

5-<(9-oxoxanthen-3-yl)oxy>valeric acid
161110-86-7

5-<(9-oxoxanthen-3-yl)oxy>valeric acid

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

ethyl 5-<(9-oxoxanthen-3-yl)oxy>valerate
161110-85-6

ethyl 5-<(9-oxoxanthen-3-yl)oxy>valerate

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

5-(xanthen-3-yloxy)valeric acid

5-(xanthen-3-yloxy)valeric acid

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

5-[9-(9H-Fluoren-9-ylmethoxycarbonylamino)-9H-xanthen-3-yloxy]-pentanoic acid

5-[9-(9H-Fluoren-9-ylmethoxycarbonylamino)-9H-xanthen-3-yloxy]-pentanoic acid

Conditions
ConditionsYield
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

dichloro-acetic acid

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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

3-methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylic acid

3-methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylic acid

Conditions
ConditionsYield
With potassium iodide; potassium carbonate In water; ethyl acetate; isopropyl alcohol
(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone
131-53-3

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

2,2',4-Trihydroxybenzophenone
13087-18-8

2,2',4-Trihydroxybenzophenone

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Methacryloyl chloride
920-46-7

Methacryloyl chloride

C22H20O6

C22H20O6

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 12h;
(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone
131-53-3

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

(M,S)-7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

(M,S)-7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

7-butyl-3-methoxy-7,8-dihydro-6H-benzo[2,3]oxocino[5,4-b]benzofuran-6-one

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

3-Methoxy-12H-dibenzo-[d,g][1,3]dioxocin-6-carboxylic Acid
133704-96-8

3-Methoxy-12H-dibenzo-[d,g][1,3]dioxocin-6-carboxylic Acid

Conditions
ConditionsYield
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

(2-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

Methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylate
133704-94-6

Methyl 3-Methoxy-12H-dibenzo[d,g][1,3]dioxocin-12-one-6-carboxylate

Conditions
ConditionsYield
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-hydroxy-4-methoxyphenyl)(2-hydroxyphenyl)-methanone

A

2,2',4-Trihydroxybenzophenone
13087-18-8

2,2',4-Trihydroxybenzophenone

B

(2,4-dihydroxyphenyl)(2-hydroxy-4-methoxyphenyl)methanone
7392-62-3

(2,4-dihydroxyphenyl)(2-hydroxy-4-methoxyphenyl)methanone

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

131-53-3Relevant articles and documents

2. 2' - dihydroxy - 4 - methoxy benzophenone preparation method

-

Paragraph 0028; 0029; 0032; 0033; 0036; 0037; 0040-0045, (2017/08/26)

A preparation method of 2,2'-dihydroxy-4-methoxybenzophenone comprises the following steps: synthesizing 2,2'4-trihydroxybenzophenone from salicylic acid and resorcinol, and carrying out a methylation reaction on 2,2'4-trihydroxybenzophenone and dimethyl sulfate to prepare 2,2'-dihydroxy-4-methoxybenzophenone. The method has the advantages of high purification efficiency, good separation effect of byproducts, high product purity reaching 99.5%, and realization of industrial production requirements of the above product.

Rh-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones

Rao, Maddali L. N.,Ramakrishna, Boddu S.

, p. 75505 - 75511 (2016/08/24)

An efficient rhodium-catalyzed direct synthesis of 2,2′-dihydroxybenzophenones and xanthones was developed from functionalized salicylaldehydes. This approach provides an easy access to various functionalized 2,2′-dihydroxybenzophenone and xanthone core s

A 2, 2 the [...] -dihydroxy-4-methoxy benzophenone synthetic method

-

Paragraph 0028; 0029; 0031, (2017/01/12)

The invention provides a synthetic method of 2,2'-dyhydroxyl-4-methoxyl diphenyl ketone. The method comprises the following steps: (1) reacting m-benzene dimethylether with o-methoxybenzoyl chloride for 1-10 hours at the temperature of 0-80 DEG C under the irradiation of light having specific wavelength to obtain an intermediate product 2,2',4-triethoxy diphenyl ketone; (2) carrying out a selective demethylation reaction on the intermediate product 2,2',4-triethoxy diphenyl ketone obtained in the step (1) and a demethylating reagent for 5-16 hours at a reaction temperature of 40-120 DEG C and then performing water washing, liquid separation and recrystallization after the reaction ends to obtain 2,2'-dyhydroxyl-4-methoxyl diphenyl ketone (II). The method is low in reaction energy consumption, high in raw material recovery rate, simple in aftertreatment and small in environment pollution, so the method satisfies the development of environmental-friendly chemistry.

Cosmetic compositions

-

, (2014/07/08)

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

-

, (2014/10/28)

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.

Pd-catalyzed sp2 C-H hydroxylation with TFA/TFAA via weak coordinations

Rao, Yu

, p. 2472 - 2476 (2013/12/04)

An efficient sp2 C-H hydroxylation has been developed for the synthesis of a wide range of functionalized phenols with aryl ketones, benzoates, benzamides, acetanilides and sulfonamides through palladium(II) catalysis. A trifluoroacetic acid (TFA)/trifluoroacetic anhydride (TFAA) co-solvent system serves as the oxygen source and is the critical factor for weak coordination promoted C-H activation. Georg Thieme Verlag Stuttgart New York.

Broadening the catalyst and reaction scope of regio- and chemoselective C-H oxygenation: A convenient and scalable approach to 2-acylphenols by intriguing Rh(ii) and Ru(ii) catalysis

Shan, Gang,Han, Xuesong,Lin, Yun,Yu, Shanyou,Rao, Yu

supporting information, p. 2318 - 2322 (2013/04/10)

A unique Rh(ii) and Ru(ii) catalyzed C-H oxygenation of aryl ketones and other arenes has been developed for the facile synthesis of diverse functionalized phenols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by gram-scale synthesis of a few different 2-acylphenols. Its utility has been well exemplified in further applications in heterocycle synthesis and direct modifications of drug Fenofibrate.

Synthesis of ortho-acylphenols through the palladium-catalyzed ketone-directed hydroxylation of arenes

Mo, Fanyang,Trzepkowski, Louis J.,Dong, Guangbin

supporting information, p. 13075 - 13079 (2013/02/25)

ortho-Acylphenols are an important structural motif found in a diversity of bioactive molecules ranging from natural products to drugs (Figure 1). Moreover, they also serve as versatile building blocks for the synthesis of various pharmaceuticals, such as warfarin, as well as agrichemicals, flavors, and fragrances. Classic approaches to the synthesis of o-acylphenols generally involve a two-step process: acylation of phenols followed by Fries rearrangement of the resulting phenyl esters (Scheme 1a). On the other hand, direct C-acylation of phenols has also been known under more forcing conditions. Although effective, these approaches are often complicated by the formation of undesired p-substituted products when bulky acyl groups need to be introduced, as well as the limited variety of ketones that can be generated.

Pd-catalyzed C-H oxygenation with TFA/TFAA: Expedient access to oxygen-containing heterocycles and late-stage drug modification

Shan, Gang,Yang, Xinglin,Ma, Linlin,Rao, Yu

supporting information, p. 13070 - 13074 (2013/02/26)

Functionalized phenols are valuable industrial chemicals related to pharmaceuticals, agrochemicals, and polymers. Therefore, the direct catalytic hydroxylation of arenes to produce phenols has attracted much attention. Although tremendous progress has been made in this field, there are still difficult substrates which remain unmet challenges for direct hydroxylation in terms of regio- and chemoselectivity, as well as the practicality of current methods (Scheme 1). For example, 2-hydroxy aromatic ketones are useful synthetic intermediates for the preparation of various oxygen-containing heterocycles such as benzofuranone, chromanone, benzoxazole, and dibenzooxazepine; they also serve as key building blocks for drugs such as celiprolol, acebutolol, and propafenone. Traditional strategies for accessing 2-hydroxy aromatic ketones have mainly involved the oxidation of benzylic alcohols, the hydrolysis of aromatic halides, Fries rearrangement of esters or the demethylation of methyl phenyl ether. These methods generally suffer from one limitation or another, such as tedious reaction procedures, harsh reaction conditions, low yields, or the formation of side products. Hence, direct transformation of readily available aromatic ketones into valuable 2-hydroxylated products by transition metal-catalyzed C-H functionalization is arguably a highly efficient and atom-economic method to access these compounds. Moreover, developing a more general strategy for the regio- and chemoselective C-H oxygenation of a variety of challenging arenes would be especially desirable for phenol synthesis (Scheme 1).

Method of purifying arylphenones

-

, (2008/06/13)

Hydroxy and alkyloxy benzophenones, also known as arylphenones, are efficiently and economically purified by contacting them with inorganic phosphorous compounds in the presence of a non-polar solvent. Best results are obtained when the arylphenone is then treated with an activated carbon and/or activated clay.

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