Ethyl ether

Diethyl ether

Names
IUPAC name Ethoxyethane
Other names Diethyl ether; Dether; Ethyl ether; Ethyl oxide; 3-Oxapentane; Ethoxyethane; Diethyl oxide; Solvent ether; Sulfuric ether
Identifiers
CAS Number	60-29-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:35702 Y
ChEMBL	ChEMBL16264 Y
ChemSpider	3168 Y
ECHA InfoCard	100.000.425
KEGG	D01772 Y
PubChem	3283
RTECS number	KI5775000
UNII	0F5N573A2Y Y
InChI InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Y Key: RTZKZFJDLAIYFH-UHFFFAOYSA-N Y InChI=1/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3 Key: RTZKZFJDLAIYFH-UHFFFAOYAB
SMILES CCOCC
Properties
Chemical formula	C4H10O
Molar mass	74.12 g·mol−1
Appearance	Colorless liquid
Odor	pungent, sweetish odor
Density	0.7134 g/cm3, liquid
Melting point	−116.3 °C (−177.3 °F; 156.8 K)
Boiling point	34.6 °C (94.3 °F; 307.8 K)
Solubility in water	69 g/L (20 °C)
Vapor pressure	440 mmHg (20°C)
Magnetic susceptibility (χ)	-55.1·10−6 cm3/mol
Refractive index (nD)	1.353 (20 °C)
Viscosity	0.224 cP (25 °C)
Structure
Dipole moment	1.15 D (gas)
Thermochemistry
Specific heat capacity (C)	172.5 J/mol·K
Std molar entropy (So298)	253.5 J/mol·K
Std enthalpy of formation (ΔfHo298)	-271.2 ± 1.9 kJ/mol
Std enthalpy of combustion (ΔcHo298)	-2732.1 ± 1.9 kJ/mol
Pharmacology
ATC code	N01AA01 (WHO)
Hazards
Main hazards	Extremely Flammable, harmful to skin, decomposes to explosive peroxides in air and light
Safety data sheet	See: data page External MSDS
R-phrases	R12 R19 R20/22 R66 R67
S-phrases	S9 S16 S29 S33
NFPA 704	4 2 1
Flash point	−45 °C (−49 °F; 228 K)
Autoignition temperature	160 °C (320 °F; 433 K)
Explosive limits	1.9-48.0%
Lethal dose or concentration (LD, LC):
LC50 (median concentration)	73,000 ppm (rat, 2 hr) 6500 ppm (mouse, 1.65 hr)
LCLo (lowest published)	106,000 ppm (rabbit) 76,000 ppm (dog)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 400 ppm (1200 mg/m3)
REL (Recommended)	No established REL
IDLH (Immediate danger)	1900 ppm
Related compounds
Related Ethers	Dimethyl ether Methoxypropane
Related compounds	Diethyl sulfide Butanols (isomer)
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Diethyl ether or simply ether, is an organic compound in the ether class with the formula (C
2H
5)
2O. It is a colorless, highly volatile flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

The compound may have been created by either Jābir ibn Hayyān in the 8th century or Ramon Llull in 1275, although there is no contemporary evidence of this. It was first synthesized in 1540 by Valerius Cordus, who called it "sweet oil of vitriol" (oleum dulce vitrioli) — the name reflects the fact that it is obtained by distilling a mixture of ethanol and sulfuric acid (then known as oil of vitriol) — and noted some of its medicinal properties. At about the same time, Paracelsus discovered ether's analgesic properties in chickens. The name ether was given to the substance in 1729 by August Sigmund Frobenius.