Bisphenoxyethanolfluorene

Bisphenoxyethanolfluorene Property

Melting point:

117-120 °C(lit.)

Boiling point:

610.7±55.0 °C(Predicted)

Density 

1.248±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

Water Solubility 

Insoluble in water

form 

powder to crystal

pka

13.95±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C29H26O4/c30-17-19-32-23-13-9-21(10-14-23)29(22-11-15-24(16-12-22)33-20-18-31)27-7-3-1-5-25(27)26-6-2-4-8-28(26)29/h1-16,30-31H,17-20H2

InChIKey

NQXNYVAALXGLQT-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(OCCO)C=C2)(C2=CC=C(OCCO)C=C2)C2=C(C=CC=C2)C2=C1C=CC=C2

CAS DataBase Reference

117344-32-8(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

37

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29094990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P330Rinse mouth.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

Bisphenoxyethanolfluorene Chemical Properties,Usage,Production

Chemical Properties

White powder

Uses

4,4′-(9-Fluorenylidene)bis(2-phenoxyethanol) may be used for the following syntheses:

• poly-(carbotetramethyldisiloxane)s, containing poly[oxy{4,4′-(9-fluorenylidene)bis(2-phenoxyethylene)}oxytetramethyldisiloxane] (a fluorescent aromatic chromophore group)
• poly[oxy(arylene)oxy(tetramethyldisilylene)]s, containing fluorescent aromatic chromophore groups in the polymer main chain, via melt copolymerization reaction with 1,2-bis(diethylamino)tetramethyldisilane

General Description

4,4′-(9-Fluorenylidene)bis(2-phenoxyethanol) is an aryldiol.

Synthesis

The general procedure of Example 12 was as follows:(a) In a glass reactor equipped with a stirrer, a nitrogen introduction tube, a thermometer and a T-tube, 80.0 g (0.444 mol) of 9-fluorenone, 613.5 g (4.44 mol) of 2-phenoxyethanol and 2.0 g of tungstophosphoric acid catalyst [(H3PW12O40).nH2O] were added. (b) The mixture was reacted at 130°C for 4 hours under reduced pressure of 2.0 x 1.03 Pa. Upon completion of the reaction, the amount of polymers in the reaction mixture was 3.9%. To the reaction mixture was added 800.0 g of toluene, neutralized with aqueous sodium hydroxide and washed with water to separate the organic phase. Toluene and excess 2-phenoxyethanol were removed from the organic phase by concentration under reduced pressure. To the concentrate was added 560.0 g of toluene, and the mixture was heated and stirred at 80 °C for 1 hour, then cooled to 70 °C. 0.4 g of 9,9-bis[(4-(2-hydroxyethoxy)phenyl)]fluorene was added as a crystalline species, and the mixture was held at 70°C for 2 hours and then cooled to 20°C. The precipitated crystals were filtered and dried to give 78.0 g of white crystals 9,9-bis[(4-(2-hydroxyethoxy)phenyl)]fluorene (yield: 90.2%, purity: 99.2%). The melting point of the resulting product was 163 °C.

References

[1] Patent: US2012/29244, 2012, A1. Location in patent: Page/Page column 15
[2] Patent: JP6139508, 2017, B2. Location in patent: Paragraph 0024
[3] Patent: EP2123625, 2009, A1. Location in patent: Page/Page column 6
[4] Chemistry Letters, 1998, # 10, p. 1055 - 1056
[5] Chemistry Letters, 1998, # 10, p. 1055 - 1056