Di-n-propyl ether

Dipropyl ether is the symmetrical ether of two n-propyl groups. It is a colorless, flammable liquid with a sweet odor typical of ethers.

Di-n-propyl ether

Names
Preferred IUPAC name 1-Propoxypropane
Other names Propyl ether, di- Dipropyl ether, normal isomer Di-n-propyl ether
Identifiers
CAS Number	111-43-3 Y
3D model (JSmol)	Interactive image
ChemSpider	7823
ECHA InfoCard	100.003.518
PubChem CID	8114
UNII	42Q250HS4G Y
CompTox Dashboard (EPA)	DTXSID8042343
InChI InChI=1S/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3 Key: POLCUAVZOMRGSN-UHFFFAOYSA-N InChI=1/C6H14O/c1-3-5-7-6-4-2/h3-6H2,1-2H3 Key: POLCUAVZOMRGSN-UHFFFAOYAT
SMILES O(CCC)CCC
Properties
Chemical formula	C6H14O
Molar mass	102.177 g·mol−1
Appearance	Colorless liquid
Density	0.75 g/cm3[1]
Melting point	−122 °C (−188 °F; 151 K)[1]
Boiling point	90 °C (194 °F; 363 K)[1]
Solubility in water	3 g/L (20 °C)
Hazards
NFPA 704 (fire diamond)	1 3 1
Flash point	−18 °C (0 °F; 255 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Preparation

Acid catalyzed ether synthesis

Dipropyl ether can be synthesized by reacting two molecules of n-propanol in the presence of p-toluenesulfonic acid (a strong acid) and heat, in the same way other symmetrical ethers may be formed.^[2]

Williamson ether synthesis

This ether may also be prepared by way of the Williamson ether synthesis in which n-propoxide, the conjugate base of n-propanol, is reacted with an n-propyl halide:^[3]

Safety

As is typical of ethers, dipropyl ether may slowly form explosive organic peroxides over long periods in storage.^[2] Antioxidants such as butylated hydroxytoluene are often added to ethers to prevent this process.^[4]

Due to the shock and light sensitive nature of organic peroxides, dipropyl ether should never be boiled or evaporated to dryness. This concentrates peroxides that may be present, which can then detonate unexpectedly destroying the vessel in which they have deposited or igniting nearby flammable liquids.^[5]

See also

• Diisopropyl ether