Basic information
- CAS
104-66-5- Standard SMILES
c1ccc(OCCOc2ccccc2)cc1- InChIKey
XCSGHNKDXGYELG-UHFFFAOYSA-N- Molecular formula
- C14H14O2
- Average molar mass
- 214.26 g/mol
- Monoisotopic mass
- 214.09937969
Overview
structure in first source
Names & identifiers
- Preferred name
- 1,2-Diphenoxyethane
- IUPAC
- 2-phenoxyethoxybenzene
- English name
- 1,2-Diphenoxyethane
- Molecular formula
- C14H14O2
- Molecular weight
- 214.26
Names & synonyms
1,2-DIPHENOXYETHANE104-66-5Ethylene glycol diphenyl etherEthane, 1,2-diphenoxy-2-Phenoxyethyl phenyl etherBenzene, 1,1'-[1,2-ethanediylbis(oxy)]bis-Benzene, 1,1'-(1,2-ethanediylbis(oxy))bis-DTXSID5026706NSC-6794V9W31HX4AWDTXCID406706RefChem:906752
Show more names
Diphenoxy Ethane1,2-Diphenoxyethansym-DiphenoxyethaneDomiphen Impurity 5Diphenoxyethane (DPE)Ethane,1,2-diphenoxy-
203-224-92-phenoxyethoxybenzeneDiphenyl GlycolDiphenyl Cellosolve(2-Phenoxyethoxy)benzenediphenoxyethaneMFCD00003039NSC 6794
Database identifiers
- CAS
104-66-5、25852-90-8- PubChem CID
- 7713
- DTXSID
DTXSID5026706- ChEMBL
CHEMBL1901367- UNII
- V9W31HX4AW
- EC Number
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 150
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Other Aromatic Compounds
Antioxidant
SpringerMaterials PropertiesChemical shift
LogP3.81
Vapor Pressure0.000314 [mmHg]
Physical DescriptionOff-white powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 94 · 94-96 °C (lit.)
- Boiling point
- 185 °C · 185 °C / 12mmHg
- Density
- 1.0781 · 1.0781 (rough estimate)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 1.557 · 1.5570 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
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 InformationIMAP assessments - Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis-: Human health tier I assessment
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS] See Benzyl ether.
Hazard Classes and CategoriesAquatic Chronic 2 (100%)
Safety & protection
Protective Action Criteria (PAC)
30 [mg/m3]
330 [mg/m3]
Chemistry & industry
Uses & manufacturing
U.S. Production2020: 66,469 lb
General Manufacturing Information
Benzene, 1,1'-[1,2-ethanediylbis(oxy)]bis-: ACTIVE
Poly(oxy-1,2-ethanediyl), .alpha.-phenyl-.omega.-phenoxy-: INACTIVE
Applications
Uses1,2-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 Description1,2-Diphenoxyethane is the intermediate formed during sonochemical oxidation of phenoxyacetic acid and chlorophenol.
Preparation methods
PreparationThe 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%.
Upstream & downstream products
Upstream raw materials
Related reactions
4 records
Compound notes
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