2,3,4,4'-Tetrahydroxybenzophenone Chemical Properties

Melting point:

199-204°C

Boiling point:

519.0±50.0 °C(Predicted)

Density 

1.526±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

7.38±0.40(Predicted)

color 

Light yellow to Amber to Dark green

Water Solubility 

15.07g/L(24.99 ºC)

InChI

InChI=1S/C13H10O5/c14-8-3-1-7(2-4-8)11(16)9-5-6-10(15)13(18)12(9)17/h1-6,14-15,17-18H

InChIKey

ZRDYULMDEGRWRC-UHFFFAOYSA-N

SMILES

C(C1=CC=C(O)C=C1)(C1=CC=C(O)C(O)=C1O)=O

CAS DataBase Reference

31127-54-5(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2914500090

2,3,4,4'-Tetrahydroxybenzophenone Usage And Synthesis

Chemical Properties

Yellow powder

Uses

2,3,4,4'-Tetrahydroxybenzophenone can be used for positive resist composition.

Preparation

Preparation by benzoylation of pyrogallol with p-hydroxybenzoic acid in the presence of Amberlyst-15 in refluxing toluene for 21 h under azeotropical removal of water (86%).

Synthesis

General procedure for the synthesis of (4-hydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone from o-hydroxybenzenetriol and p-hydroxybenzoic acid: 0.11 moles of p-hydroxybenzoic acid and 0.1 moles of pyrophosphoric acid as an acylating agent as well as 0.015 moles of concentrated sulfuric acid were added in a reactor and mixed well. An inert gas was passed for 10 minutes to remove air. After increasing the system temperature to 70-80°C, the reactor was closed, the temperature was adjusted to 110-130°C, the pressure was maintained at 0.1-5 MPa and the reaction was carried out for 3 hours. Upon completion of the reaction, the reaction mixture was cooled to 50-60 °C and held at this temperature for 1.5 hours. Subsequently, 200 ml of 20% ethanol solution was added and crystallized at 0-5°C. The crystals were collected by filtration and dried to give the target product (4-hydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone. The molar yield of this step was 78.16% and the purity was ≥98.5% by HPLC.

References

[1] Patent: CN106349036, 2017, A. Location in patent: Paragraph 0032-0037
[2] Patent: CN106365961, 2017, A. Location in patent: Paragraph 0030; 0031; 0032; 0033; 0034; 0035
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 2, p. 482
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 2, p. 483
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 2, p. 483

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