131-54-4

Basic information

• Product Name: 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
• 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
• CAS NO: 131-54-4
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27
• EINECS: 205-027-3
• 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
• Mol File: 131-54-4.mol

Chemical Properties

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

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-22
• WGK Germany: 3
• RTECS: DJ0900000
• TSCA: Yes
• Hazardous Substances Data: 131-54-4(Hazardous Substances Data)

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.

Synthetic route

2-Hydroxy-4-methoxybenzaldehyde (673-22-3) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

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;	76%

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%

O-methylresorcine (150-19-6) + [(bromodifluoromethyl)sulfanyl]benzene (78031-08-0) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
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) + 4-methoxysalicylic acid (2237-36-7) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate

2,2',4,4'-tetramethoxybenzophenone (3555-85-9) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
With aluminium trichloride; 1,2-dichloro-ethane

2,4-dimethoxybenzoyl chloride (39828-35-8) + 1,3-Dimethoxybenzene (151-10-0) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
With aluminium trichloride; N,N-dimethyl-formamide; chlorobenzene

1,3-Dimethoxybenzene (151-10-0) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
With aluminium trichloride; 1,2-dichloro-ethane unter Zusatz von NaCl und KCl oder ZnCl2;

thiophenol (108-98-5) → bis(2-hydroxy-4-methoxyphenyl)-methanone (131-54-4)

Conditions	Yield
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

Upstream product

• 150-19-6 O-methylresorcine 
• 2237-36-7 4-methoxysalicylic acid 
• 3555-85-9 2,2',4,4'-tetramethoxybenzophenone 
• 39828-35-8 2,4-dimethoxybenzoyl chloride 
• 151-10-0 1,3-Dimethoxybenzene 
• 78031-08-0 [(bromodifluoromethyl)sulfanyl]benzene 
• 108-98-5 thiophenol 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 90-02-8 salicylaldehyde 
• 131-55-5 2,2',4,4'-tetrahydroxybenzophenone 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 4142-51-2 (2-hydroxy-4-methoxyphenyl) (2',4'-dimethoxyphenyl)methanone 
• 143982-77-8 2,2'-dihydroxy-4,4'-dimethoxybenzophenone-5,5'-disulfonic acid 
• 7392-62-3 (2,4-dihydroxyphenyl)(2-hydroxy-4-methoxyphenyl)methanone 
• 1285538-95-5 C₁₈H₂₀O₅ 
• 1285538-97-7 7-methoxy-2-methyl-4-(2-hydroxy-4-methoxyphenyl)-2H-chromene 
• 3555-85-9 2,2',4,4'-tetramethoxybenzophenone 
• 131-55-5 2,2',4,4'-tetrahydroxybenzophenone 
• 81095-44-5 3,4:8,9-bis(4'-methoxybenzo)-5,7-bis(2',4'-dimethoxyphenyl)-1-phenyl-2,6,10,11-tetraoxa-1-phospha(V)tricyclo<5.3.1.0^1,5>undecane 

Relevant articles and documents

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

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

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

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.

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

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