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2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is an organic compound characterized by its yellow crystalline powder form. It is known for its ability to absorb ultraviolet light, making it a valuable additive in various industries.

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  • 131-54-4 Structure
  • Basic information

    1. Product Name: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
    2. Synonyms: Benzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-;bis(2-hydroxy-4-methoxyphenyl)-methanon;Cyasorb UV 12;cyasorbuv12;Methanone, bis(2-hydroxy-4-methoxyphenyl)-;Methanone,bis(2-hydroxy-4-methoxyphenyl)-;2.2''-DIHYD[CL]ROXY-4.4''-DIMETHY1[E]BENZOPHENONE;Cyasorb UV
    3. CAS NO:131-54-4
    4. Molecular Formula: C15H14O5
    5. Molecular Weight: 274.27
    6. EINECS: 205-027-3
    7. Product Categories: INORGANIC & ORGANIC CHEMICALS;Aromatic Benzophenones & Derivatives (substituted);Benzophenones (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Polymer Additives;Polymer Science;Stabilizers
    8. Mol File: 131-54-4.mol
  • Chemical Properties

    1. Melting Point: 133-136 °C(lit.)
    2. Boiling Point: 377.26°C (rough estimate)
    3. Flash Point: 164.4 ºC
    4. Appearance: Yellow crystalline powder
    5. Density: 1.2662 (rough estimate)
    6. Refractive Index: 1.5000 (estimate)
    7. Storage Temp.: 2-8°C(protect from light)
    8. Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
    9. PKA: 6.81±0.35(Predicted)
    10. Water Solubility: negligible
    11. Merck: 14,1099
    12. BRN: 1887087
    13. CAS DataBase Reference: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone(CAS DataBase Reference)
    14. NIST Chemistry Reference: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone(131-54-4)
    15. EPA Substance Registry System: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone(131-54-4)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-37/39-22
    4. WGK Germany: 3
    5. RTECS: DJ0900000
    6. TSCA: Yes
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 131-54-4(Hazardous Substances Data)

131-54-4 Usage

Uses

Used in Paint Industry:
2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is used as an ultraviolet light absorber for protecting paint coatings from the harmful effects of UV radiation. This helps to prevent fading, discoloration, and degradation of the paint, thereby enhancing its durability and longevity.
Used in Plastics Industry:
In the plastics industry, 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is utilized as an additive to shield plastics from the damaging effects of ultraviolet light. This is particularly important for plastics that are exposed to sunlight or other sources of UV radiation, as it helps to maintain their physical properties, color, and appearance over time.

Preparation

preparation by reaction of 2-hydroxy-4-methoxy-benzoic acid with resorcinol monomethyl ether in the presence of zinc chloride and phosphorous oxychloride at 7075° for 2.

Check Digit Verification of cas no

The CAS Registry Mumber 131-54-4 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 4 respectively.
Calculate Digit Verification of CAS Registry Number 131-54:
(5*1)+(4*3)+(3*1)+(2*5)+(1*4)=34
34 % 10 = 4
So 131-54-4 is a valid CAS Registry Number.

131-54-4SDS

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-4,4'-dimethoxybenzophenone

1.2 Other means of identification

Product number -
Other names 4,4'-di-methoxy,2,2'-di-ol-benzophenone

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:131-54-4 SDS

131-54-4Synthetic route

2-Hydroxy-4-methoxybenzaldehyde
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

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

bis(2-hydroxy-4-methoxyphenyl)-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;76%
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%
O-methylresorcine
150-19-6

O-methylresorcine

[(bromodifluoromethyl)sulfanyl]benzene
78031-08-0

[(bromodifluoromethyl)sulfanyl]benzene

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

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

Conditions
ConditionsYield
Stage #1: [(bromodifluoromethyl)sulfanyl]benzene With titanium tetrachloride In dichloromethane at 20℃; for 0.25h; Friedel Crafts type alkylation; Inert atmosphere;
Stage #2: O-methylresorcine In dichloromethane at 20℃; for 16h; Friedel Crafts type alkylation; Inert atmosphere;
10%
O-methylresorcine
150-19-6

O-methylresorcine

4-methoxysalicylic acid
2237-36-7

4-methoxysalicylic acid

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

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

Conditions
ConditionsYield
With zinc(II) chloride; trichlorophosphate
2,2',4,4'-tetramethoxybenzophenone
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

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

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

Conditions
ConditionsYield
With aluminium trichloride; 1,2-dichloro-ethane
2,4-dimethoxybenzoyl chloride
39828-35-8

2,4-dimethoxybenzoyl chloride

1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

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

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

Conditions
ConditionsYield
With aluminium trichloride; N,N-dimethyl-formamide; chlorobenzene
1,3-Dimethoxybenzene
151-10-0

1,3-Dimethoxybenzene

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

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

Conditions
ConditionsYield
With aluminium trichloride; 1,2-dichloro-ethane unter Zusatz von NaCl und KCl oder ZnCl2;
thiophenol
108-98-5

thiophenol

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere
1.2: 3 h / -60 °C / Inert atmosphere
2.1: titanium tetrachloride / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
2.2: 16 h / 20 °C / Inert atmosphere
View Scheme

131-54-4Relevant articles and documents

Water-soluble ultraviolet absorbent BP-9 method for the synthesis of (by machine translation)

-

Paragraph 0006; 0025; 0026, (2017/01/17)

The invention discloses a synthetic method of a water soluble ultraviolet light absorber BP-9. The method mainly comprises the following process steps: (1) carrying out methylation on the main raw materials of 2, 2', 4, 4'-tetrahydroxyl benzophenone, a transition metal salt catalyst and a mixed solvent which is prepared from dichloroethane and anhydrous ethanol in equal parts by weight to obtain 2, 2'-dihydroxyl-4, 4'-dimethoxyl benzophenone; (2) carrying out sulfonation reaction on the main raw materials of methylate, sulfamic acid and C1-C3 halohydrocarbon to obtain 2, 2'-dihydroxyl-4, 4'-dimethoxyl benzophenone-5, 5'-disulfonic acid; and (3) carrying out neutral reaction on the main raw materials of sulfonated product, inorganic base and ethanol water to finally obtain the BP-9 product. The synthetic method disclosed by the invention is few in reaction step, low in cost, high in product purity and stable in quality, and raw materials are easily available.

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

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.

Friedel-crafts-type alkylation with bromodifluoro(phenylsulfanyl)methane through α-fluorocarbocations: Syntheses of thioesters, benzophenones and xanthones

Kuhakarn, Chutima,Surapanich, Nakin,Kamtonwong, Siriporn,Pohmakotr, Manat,Reutrakul, Vichai

, p. 5911 - 5918 (2011/12/05)

Bromodifluoro(phenylsulfanyl)methane undergoes a Friedel-Crafts-type alkylation, through α-fluorocarbocations, with activated aromatic compounds yielding thioesters and/or benzophenones. The methodology has been applied to the synthesis of naturally occurring xanthone derivatives.

SUNSCREEN COMPOSITIONS

-

, (2008/06/13)

The present invention relates to improved sunscreen compositions, more preferably to improved sunscreen compositions containing at least one sunscreening agent (sunscreen) and a silicone-polyamide copolymer.

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.

Transparent cosmetic composition that reflects infrared radiation and its use for protecting the human epidermis against infrared radiation

-

, (2008/06/13)

Transparent cosmetic composition that reflects infrared radiation and its use for protecting the human epidermis against infrared radiation. The invention relates to a transparent cosmetic composition comprising, by way of an agent that reflects infrared radiation for protecting the human epidermis, a substance which is dispersible in the cosmetic medium used, possessing a reflectance (R) of infrared radiation equal to at least 45%, and of which a 2% strength dispersion in vaseline possesses an optical transmission in the visible of at least 85%, chosen from a diatom of particle size less than 100 microns, hollow glass microspheres of size less than 100 microns, a bismuth oxychloride of particle size less than 75 microns and zirconium powder covered ceramic microparticles of particle size less than 8 microns. This cosmetic composition can also contain 0.5 to 20% by weight of UV-A, UV-B or broad-band screening agents.

Light-stable screening cosmetic composition containing bixin combined with a lipid-soluble UV filter and its use for protecting the human epidermis against ultra-violet radiation

-

, (2008/06/13)

The invention relates to a light-stable cosmetic composition for protecting the human epidermis against UV radiation, containing at least 0.0025% by weight of bixin combined with at least 1% by weight of one or more lipid-soluble agents screening UV radiation, chosen from 3-benzylidene-dl-camphor, its derivatives and benzophenone derivatives, in a cosmetically acceptable vehicle comprising at least one fatty phase. The bixin takes the form of an oily extract of annatto containing at least 0.1% by weight of bixin.

High molecular weight piperidine derivatives as UV stabilizers

-

, (2008/06/13)

Substituted high molecular weight hindered spiropiperidine compounds and polymer compositions stabilized by these compounds. The spiropiperidine compounds are prepared by reacting hindered 4-piperidinone hydrochloride with an activated benzene, such as resorcinol, in an acid medium.

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