Dibutyl ether

Dibutyl ether
Names
	Preferred IUPAC name 1-Butoxybutane
	Other names Di-n-butyl ether; Butyl ether; n-Butyl ether;
Identifiers
CAS Number	142-96-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	8569;
ECHA InfoCard	100.005.069
PubChem CID	8909;
UNII	PBM2R52P5G ;
CompTox Dashboard (EPA)	DTXSID1022007 ;
	InChI InChI=1S/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYSA-N; InChI=1/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYAH;
	SMILES CCCCOCCCC;
Properties
Chemical formula	C8H18O
Molar mass	130.231 g·mol−1
Appearance	Colorless liquid
Odor	Fruity
Density	0.77 g/cm3 (20 °C)
Melting point	−95 °C (−139 °F; 178 K)
Boiling point	141 °C (286 °F; 414 K)
Solubility in water	0.3 g/L
Refractive index (nD)	1.3992
Viscosity	0.741 cP (15 °C)
Structure
Dipole moment	1.18 D
Hazards
Flash point	25 °C (77 °F; 298 K)
Autoignition; temperature	175 °C (347 °F; 448 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	7400 mg/kg (oral, rat)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dibutyl ether is a chemical compound belonging to the ether family with the molecular formula of C
₈H
₁₈O. It is colorless, volatile, and flammable liquid and has peculiar ethereal smell.

Liquid dibutyl ether is lighter than water. On the other hand, the vapor is heavier than air. It is not soluble in water, but it is soluble in acetone and many other organic solvents. Due to this property, dibutyl ether is used as solvent in various chemical reactions and processes. For example, phenyllithium is commercially available as a ca. 1.8M solution in dibutyl ether.

Because of the formation of peroxides, it should be protected from heat, light and air.

Synthesis

Dibutyl ether is obtained from dehydration of 1-butanol with sulfuric acid as a catalyst and dehydrating agent:

2C
₄H
₉OH → C
₈H
₁₈O + H
₂O

Industrially, dibutyl ether can be obtained by dehydration of 1-butanol on alumina at 300 °C.^{[citation needed]}

Reactions

This compound is generally stable to oxidation, reduction, and base. Strong acids like HI and HBr can cleave this ether. In the presence of oxygen, dibutyl ether is oxidized to a peroxide or hydroperoxide.

Applications

Solvent for Grignard syntheses
Solvent for fats, oils, organic acids, alkaloids, natural and synthetic resins
For manufacturing of pesticides (e.g. cyhexatin)

References

^ ^a ^b ^c ^d ^e ^f ^g ^h Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[GESTIS-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[1]

Names

Preferred IUPAC name 1-Butoxybutane
Other names Di-n-butyl ether Butyl ether n-Butyl ether
Identifiers
CAS Number	142-96-1^Y
3D model (JSmol)	Interactive image
ChemSpider	8569
ECHA InfoCard	100.005.069
PubChem CID	8909
UNII	PBM2R52P5G^Y
CompTox Dashboard (EPA)	DTXSID1022007
InChI InChI=1S/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYSA-N InChI=1/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3 Key: DURPTKYDGMDSBL-UHFFFAOYAH
SMILES CCCCOCCCC
Properties
Chemical formula	C₈H₁₈O
Molar mass	130.231 g·mol⁻¹
Appearance	Colorless liquid^[1]
Odor	Fruity^[1]
Density	0.77 g/cm³ (20 °C)^[1]
Melting point	−95 °C (−139 °F; 178 K)^[1]
Boiling point	141 °C (286 °F; 414 K)^[1]
Solubility in water	0.3 g/L^[1]
Refractive index (n_D)	1.3992
Viscosity	0.741 cP (15 °C)
Structure
Dipole moment	1.18 D
Hazards
Flash point	25 °C (77 °F; 298 K)
Autoignition temperature	175 °C (347 °F; 448 K)^[1]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	7400 mg/kg (oral, rat)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references