1,2-Diphenoxyethane
1,2-DIPHENOXYETHANE · ETHYLENE GLYCOL DIPHENYL ETHER · DIPHENYL GLYCOL · Diphenoxy Ethane · 1,2-Diphenoxyethan · sym-Diphenoxyethane · DIPHENYL CELLOSOLVE · Domiphen Impurity 5
Identifiers & Physical Properties
| CAS No. | 104-66-5 |
|---|---|
| Molecular formula | C14H14O2 |
| Average molar mass | 214.26 g/mol |
| Monoisotopic mass | 214.09937969 g/mol |
| SMILES | c1ccc(OCCOc2ccccc2)cc1 |
| InChIKey | XCSGHNKDXGYELG-UHFFFAOYSA-N |
| PubChem CID | 7713 |
| ChEMBL | CHEMBL1901367 |
| EC No. | 203-224-9 |
| DTXSID | DTXSID5026706 |
Chemical & Physical Properties
| XLogP | 3.8 |
|---|---|
| Topological polar surface area | 18.5 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 5 |
| Heavy atoms | 16 |
| Formal charge | 0 |
| Complexity | 150 |
| Chemical classes | Other Classes -> Other Aromatic CompoundsAntioxidant |
| SpringerMaterials Properties | Chemical shift |
| LogP (partition coefficient) | 3.81 |
| Vapor pressure | 0.000314 [mmHg]0Pa at 25℃ |
| Physical Description | Off-white powder[Alfa Aesar MSDS] |
| Melting point | 94-96 °C (lit.) |
| Boiling point | 185 °C / 12mmHg |
| Density | 1.0781 (rough estimate) |
| Refractive index | 1.5570 (estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | Chloroform (Slightly), Methanol (Slightly)22mg/L at 25℃ |
| Physical state | Solid |
| Color | White to Off-White |
| BRN | 2052248 |
| InChI | 1S/C14H14O2/c1-3-7-13(8-4-1)15-11-12-16-14-9-5-2-6-10-14/h1-10H,11-12H2 |
| InChIKey | XCSGHNKDXGYELG-UHFFFAOYSA-N |
| SMILES | C(COc1ccccc1)Oc2ccccc2 |
| LogP (partition coefficient) | 3.81 at 25℃ |
| CAS DataBase Reference | 104-66-5(CAS DataBase Reference) |
| FDA UNII | V9W31HX4AW |
| EPA Substance Registry System | 2-Phenoxyethyl phenyl ether (104-66-5) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS09 |
| Signal word | Warning |
| GHS hazard statements | H411 |
| GHS precautionary statements | P273-P391-P501 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Risk statements (R) | 51/53 |
| Safety statements (S) | 22-24/25-61-36-29/56 |
| UN transport number | UN 3077 9 / PGIII |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29093090 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Aquatic Chronic 2 |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P273, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 5 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis-Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)FRI - indicates a polymeric substance containing no free-radical initiator in its Inventory name but is considered to cover the designated polymer made with any free-radical initiator regardless of the amount used.REACH registered substance: 1,2-diphenoxyethane (EC: 203-224-9) |
| Other safety information | IMAP assessments - Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis-: Human health tier I assessment |
| Hazards summary | May cause irritation[Alfa Aesar MSDS] See Benzyl ether. |
| Hazard Classes and Categories | Aquatic Chronic 2 (100%) |
| Protective Action Criteria (PAC) | 30 [mg/m3]330 [mg/m3]2000 [mg/m3] |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 3077 9 / PGIII |
| Customs code | 29093090 |
| Risk statements (R) | 51/53 |
| Signal word | Warning |
Applications & Uses
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.
General Description
1,2-Diphenoxyethane is the intermediate formed during sonochemical oxidation of phenoxyacetic acid and chlorophenol.
Preparation & Synthesis
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%.