9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE Chemical Properties

Melting point:

158.0 to 162.0 °C

Boiling point:

634.9±48.0 °C(Predicted)

Density 

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

storage temp. 

Sealed in dry,Room Temperature

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C24H32O6P2/c1-5-27-31(25,28-6-2)17-23-19-13-9-11-15-21(19)24(22-16-12-10-14-20(22)23)18-32(26,29-7-3)30-8-4/h9-16H,5-8,17-18H2,1-4H3

InChIKey

PKLFGXZSNISEOV-UHFFFAOYSA-N

SMILES

C(C1C2=CC=CC=C2C(CP(=O)(OCC)OCC)=C2C=CC=CC=12)P(=O)(OCC)OCC

Safety Information

HS Code 

2931.90.6000

9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE Usage And Synthesis

Uses

9,10-bis(Diethylphosphonomethyl)anthracene is used in the synthesis of compounds with imaging applications.

Synthesis

General procedure for the synthesis of 9,10-bis(diethylphosphinomethyl)anthracene from 9,10-bis(chloromethyl)anthracene and triethyl phosphite: 9,10-bis(chloromethyl)anthracene (7.8 g, 28.3 mmol) was mixed with triethyl phosphite (30 mL), and the reaction mixture was vigorously stirred under mild reflux conditions overnight. Upon completion of the reaction, the excess triethyl phosphite was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:1, v/v) as eluent. A yellow solid product (10.4 g, 76.8% yield) was finally obtained. The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 8.32 (d, 4H), 7.53 (d, 4H), 4.21 (d, 8H), 3.78 (d, 4H), 1.11 ppm (t, 12H).

References

[1] Molecular Crystals and Liquid Crystals, 2004, vol. 424, p. 119 - 126
[2] Molecular Crystals and Liquid Crystals, 2011, vol. 550, p. 233 - 239
[3] Journal of Materials Chemistry C, 2018, vol. 6, # 16, p. 4384 - 4388
[4] Journal of Materials Chemistry C, 2013, vol. 1, # 10, p. 2028 - 2035
[5] Dyes and Pigments, 2013, vol. 99, # 3, p. 833 - 838

9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE(60974-92-7)Related Product Information

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• DIETHYL 4-METHYLBENZYLPHOSPHONATE
• P-XYLYLENEDIPHOSPHONIC ACID TETRAETHYL ESTER
• 9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE
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