1,2-Diphenoxyethane Property

Melting point:

94-96 °C (lit.)

Boiling point:

185 °C / 12mmHg

Density 

1.0781 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

1.5570 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

Water Solubility 

22mg/L at 25℃

BRN 

2052248

InChIKey

XCSGHNKDXGYELG-UHFFFAOYSA-N

LogP

3.81 at 25℃

CAS DataBase Reference

104-66-5(CAS DataBase Reference)

EPA Substance Registry System

2-Phenoxyethyl phenyl ether (104-66-5)

Safety

Risk Statements 

51/53

Safety Statements 

22-24/25-61-36-29/56

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

TSCA 

Yes

HS Code 

29093090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

1,2-Diphenoxyethane Chemical Properties,Usage,Production

Structure

The homo-bichromophoric system 1,2-diphenoxyethane possesses two conformational isomers, which differ in the central O–C–C–O dihedral angle. One, which shows C2 symmetry, can be described as a trans-gauche-trans (tgt) conformer, the other with C2h symmetry as a trans-trans-trans (ttt) conformer. 1,2-diphenoxyethane (C6H5–O–CH2–CH2–O–C6H5) can be viewed as composed of two anisole (C6H5–O–CH2) radical moieties. The excitonic splitting arises from the transition dipole moments (TDM) interaction in the two individual moieties. The excitonic splitting of the two different rotamers of 1,2-diphenoxyethane is different, due to (i) different symmetry, (ii) different distance of the chromophores, and (iii) different orientation of the chromophores. However, the TDM of the individual chromophores is the same for both rotamers. The interaction energy of the two transition dipole moments in 1,2-diphenoxyethane is one wavenumber or less, which is much smaller than the reorganization energy. Vibronic coupling, therefore, is treated as weak coupling[1].

Chemical Properties

Off-white Crystals

Uses

1,2-Diphenoxyethane is a reagent that is used in the production and use of activatable delivery compounds containing drugs or a detectable moiety and singlet oxygen-labile linkers.

Preparation

The preparation of Ethylene glycol diphenyl ether is as follows:A three-necked flask was charged with 15.7 g of bromobenzene (100 mmol) and 47 ml of DMF, and stirred. 12.7 g of sodium carbonate (120 mmol, 1.2 eq.), 1.9 g of cuprous iodide (10 mmol, 0.1 eq.), 1.87 g of 2,2'-bipyridine (12 mmol, 0.1 eq.) and 7.4 g of ethylene glycol (120 mmol, 1.2 equivalent), the reaction mixture was stirred at 100 ° C overnight. After recovering DMF under reduced pressure, 100 ml of water and 100 ml of toluene were added, and the aqueous phase was extracted three times with 300 ml of toluene, and the organic layers were combined. Washed sequentially with 5% sodium carbonate. The organic phase was dried over anhydrous sodium sulfate, filtered, and then filtered and evaporated,The crude product was recrystallized from isopropanol and dried in vacuo to give 19.5 g of product, yield 91%, purity over 99%.

Application

Ethylene glycol diphenyl ether can be used as a new heat-sensitive material sensitizer and a potential polyolefin catalyst additive.

General Description

1,2-Diphenoxyethane is the intermediate formed during sonochemical oxidation of phenoxyacetic acid and chlorophenol.

Flammability and Explosibility

Non flammable

References

[1] Jascha Martini . “Structural changes of 1,2-diphenoxyethane upon electronic excitation from a combined Franck-Condon/rotational constants fit.” Journal of Molecular Structure 1270 (2022): Article 133896.