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2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
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Name

2,2'-Dihydroxy-4,4'-dimethoxybenzophenone

 EINECS 205-027-3
CAS No. 131-54-4 Density 1.291 g/cm3
PSA 75.99000 LogP 2.34600
Solubility solubility in water is negligible Melting Point 133-136 ºC
Formula C15H14O5 Boiling Point 439.3 ºC at 760 mmHg
Molecular Weight 274.273 Flash Point 164.4 ºC
Transport Information N/A Appearance Yellow crystalline powder
Safety 26-37/39-22 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 131-54-4 (2,2'-Dihydroxy-4,4'-dimethoxybenzophenone) Hazard Symbols IrritantXi
Synonyms

Benzophenone,2,2'-dihydroxy-4,4'-dimethoxy- (6CI,8CI);4,4'-Dimethoxy-2,2'-dihydroxybenzophenone;Benzophenone 6;Cyasorb UV 12;NSC 40149;Seesorb 107;Uvinul 3049;Uvinul D 49;Bis(2-hydroxy-4-methoxyphenyl)methanone;

Article Data 16

2,2'-Dihydroxy-4,4'-dimethoxybenzophenone Synthetic route

673-22-3

2-Hydroxy-4-methoxybenzaldehyde

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%
673-22-3

2-Hydroxy-4-methoxybenzaldehyde

90-02-8

salicylaldehyde

A

131-54-4

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

B

835-11-0

2,2'-dihydroxybenzophenone

C

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%
150-19-6

O-methylresorcine

78031-08-0

[(bromodifluoromethyl)sulfanyl]benzene

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%
150-19-6

O-methylresorcine

2237-36-7

4-methoxysalicylic acid

131-54-4

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

Conditions
ConditionsYield
With zinc(II) chloride; trichlorophosphate
3555-85-9

2,2',4,4'-tetramethoxybenzophenone

131-54-4

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

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

2,4-dimethoxybenzoyl chloride

151-10-0

1,3-Dimethoxybenzene

131-54-4

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

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

1,3-Dimethoxybenzene

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;
108-98-5

thiophenol

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

2,2'-Dihydroxy-4,4'-dimethoxybenzophenone Consensus Reports

Reported in EPA TSCA Inventory.

2,2'-Dihydroxy-4,4'-dimethoxybenzophenone Specification

1. Introduction of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
2,2'-Dihydroxy-4,4'-dimethoxybenzophenone is one kind of Yellow crystalline powder. Its IUPAC Name is Bis(2-hydroxy-4-methoxyphenyl)methanone. It can solubility in water is negligible. 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone belongs to 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. Classification Code: Mutation data.

2. Properties of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
Physical properties about 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone are:
(1)Melting point: 133-136 °C; (2)Index of Refraction: 1.605; (3)Molar Refractivity: 73.16 cm3; (4)Molar Volume: 212.4 cm3; (5)Surface Tension: 51.9 dyne/cm; (6)Density: 1.291 g/cm3; (7)Flash Point: 164.4 °C; (8)Enthalpy of Vaporization: 72.31 kJ/mol; (9)Boiling Point: 439.3 °C at 760 mmHg; (10)Vapour Pressure: 2.49E-08 mmHg at 25°C.

3. Structure Descriptors of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
(1)SMILES: O=C(c1ccc(OC)cc1O)c2ccc(OC)cc2O;
(2)Std. InChI: InChI=1S/C15H14O5/c1-19-9-3-5-11(13(16)7-9)15(18)12-6-4-10(20-2)8-14(12)17/h3-8,16-17H,1-2H3;
(3)Std. InChIKey: SODJJEXAWOSSON-UHFFFAOYSA-N.

4. Physical Properties of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone

Physical Property Value Units Temp (deg C) Source
Melting Point 139.5 deg C   EXP
log P (octanol-water) 3.900 (none)   EST
Atmospheric OH Rate Constant 2.02E-10 cm3/molecule-sec 25 EST

5. Toxicity of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone

1.    

mma-sat 10 µg/plate

     JACTDZ    Journal of the American College of Toxicology. 2 (5)(1983),35.

6. Safety Information of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
Hazard Codes:Xi  
Risk Statements:36/37/38
Irritating to eyes, respiratory system and skin 
Safety Statements:26-37/39-22
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37/39:Wear suitable gloves and eye/face protection
22:Do not breathe dust     
WGK Germany:3
RTECS:DJ0900000
Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.

7. Applications of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
Bis(2-hydroxy-4-methoxyphenyl)methanone (CAS NO.131-54-4) is a kind of light stabilizer benzophenone used to be ultraviolet absorbent.

2,2'-dihydroxy-4,4'-dimethoxy-benzophenone and carbonochloridic acid methyl ester can be used to manufacture 6,6'-carbonylbis(3-methoxy-6,1-phenylene) dimethyl dicarbonate. it is Et3N tetrahydrofuran 0 °C to room temp., 0.5 to 1 h.


 

8. Production of 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone
After the condensation reaction of chloroformyl chloride and m-Dimethyl bengene,the product is hydrolyzed and acidulated to get Bis(2-hydroxy-4-methoxyphenyl)methanone.

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