3-Benzenediol, 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-1 Chemical Properties

Melting point:

203.0 to 207.0 °C

Boiling point:

659.1±65.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

8.58±0.40(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C25H23N3O2/c1-14-5-8-19(16(3)11-14)23-26-24(20-9-6-15(2)12-17(20)4)28-25(27-23)21-10-7-18(29)13-22(21)30/h5-13,29-30H,1-4H3

InChIKey

FROCQMFXPIROOK-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(C2=NC(C3=CC=C(C)C=C3C)=NC(C3=CC=C(C)C=C3C)=N2)C(O)=C1

EPA Substance Registry System

1,3-Benzenediol, 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]- (1668-53-7)

Safety Information

HS Code 

2933.69.6050

3-Benzenediol, 4-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-1 Usage And Synthesis

Synthesis

The general procedure for the synthesis of 4-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)benzene-1,3-diol from 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)benzene-1,3-diol using 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl and resorcinol was carried out as follows: in a 50 mL three-necked flask protected by a dry nitrogen gas, 2-chloro-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-1,3,5-triazin-2-yl (1.6 mmol) and 2-chloro-4,6 -bis(2,4-dimethylphenyl)-1,3,5-triazine (1.6 mmol) and anhydrous aluminum trichloride (0.32 g, 2.4 mmol) to anhydrous chlorobenzene (15 mL), and the reaction mixture was stirred for 0.5 hours at 25 °C. Subsequently, resorcinol (0.24 g, 2.2 mmol) was added and the reaction mixture was warmed up to 85 °C for continued stirring for 5 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched by the slow addition of ice water (10 mL), followed by evaporation under reduced pressure to remove the chlorobenzene. The mixture was filtered and the resulting solid was washed with water (3 x 10 mL) and finally recrystallized from ethyl acetate to afford the target product 4-(4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl)benzene-1,3-diol and its derivatives.

References

[1] Journal of Fluorescence, 2018, vol. 28, # 2, p. 707 - 723
[2] Patent: US6242598, 2001, B1