• Name

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

• EINECS 205-027-3
• CAS No. 131-54-4
• Article Data16
• CAS DataBase
• Density 1.291 g/cm³
• 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
• Appearance Yellow crystalline powder
• Safety 26-37/39-22
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• 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;
• PSA 75.99000
• LogP 2.34600

Synthetic route

673-22-3

2-Hydroxy-4-methoxybenzaldehyde

131-54-4

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

Conditions

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%

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

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%

...Expand

150-19-6

O-methylresorcine

78031-08-0

[(bromodifluoromethyl)sulfanyl]benzene

131-54-4

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

Conditions

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%

150-19-6

O-methylresorcine

2237-36-7

4-methoxysalicylic acid

131-54-4

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

Conditions

Conditions	Yield
With zinc(II) chloride; trichlorophosphate

3555-85-9

2,2',4,4'-tetramethoxybenzophenone

131-54-4

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

Conditions

Conditions	Yield
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

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

151-10-0

1,3-Dimethoxybenzene

131-54-4

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

Conditions

Conditions	Yield
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

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

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

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.