n-Butyl glycidyl ether

n-Butyl glycidyl ether

Names
IUPAC name 2-(Butoxymethyl)oxirane
Other names BGE, 1,2-Epoxy-3-butoxypropane, 2,3-Epoxypropyl butyl ether, (Butoxymethyl)oxirane, 1-Butoxy-2,3-epoxypropane
Identifiers
CAS Number	2426-08-6
3D model (Jmol)	Interactive image
ECHA InfoCard	100.017.616
PubChem	17049
RTECS number	TX4200000
UNII	M03777A62S Y
UN number	1993
InChI InChI=1S/C7H14O2/c1-2-3-4-8-5-7-6-9-7/h7H,2-6H2,1H3
SMILES CCCCOCC1CO1
Properties
Chemical formula	C7H14O2
Molar mass	130.19 g·mol−1
Appearance	Colorless liquid[1]
Odor	Irritating[1]
Density	0.91 g/cm3[1]
Boiling point	164 °C; 327 °F; 437 K [1]
Solubility in water	2% (20° C)[1]
Vapor pressure	3 mmHg (25°C)[1]
Hazards
Flash point	130 °F[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	260 mg/m3 (inhalation, mouse)[2] 1030 ppm (inhalation, rat, 8 hours)[2] 700 mg/kg (intraperitoneal, mouse)[2] 1140 mg/kg (intraperitoneal, rat)[2] 1530 mg/kg (oral, mouse)[2] 1660 mg/kg (oral, rat)[2] 2520 µL/kg (skin, rabbit)[2] >2150 mg/kg (skin, rat)[2] 2050 mg/kg (oral, rat)[3]
LC50 (median concentration)	>3500 ppm (mouse, 4 hr)[3] 1030 ppm (rat, 8 hr)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 50 ppm (270 mg/m3)[1]
REL (Recommended)	5.6 ppm (30 mg/m3) [15 min][1]
IDLH (Immediate danger)	250 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive.

Synthesis

n-Butyl alcohol and epichlorohydrin react in a condensation reaction, followed by a caustic dehydrochlorination, to form n-butyl glycidyl ether.^[4]

Metabolism

n-Butyl glycidyl ether is metabolized renally to butoxyacetic acid, 3-butoxy-2-hydroxypropionic acid and 3-butoxy-2-acetylaminopropionic acid.^[4][5]

Safety

Exposure to n-butyl glycidyl ether through inhalation, eye contact, or skin exposure can cause a cough, sore throat, eye and skin redness, and pain. It is flammable and reacts with strong oxidants, strong bases, strong acids, and amines.^[6]

References

1. 1 2 3 4 5 6 7 8 9 10 "NIOSH Pocket Guide to Chemical Hazards #0081". National Institute for Occupational Safety and Health (NIOSH). 
2. 1 2 3 4 5 6 7 8 "Propane, 1-Butoxy-2,3-epoxy". CDC/NIOSH. 
3. 1 2 3 "{{{2}}}". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
4. 1 2 CID 17049 from PubChem
5. ↑ Eadsforth, C. V.; Hutson, D. H.; Logan, C. J.; Morrison, B. J. (1985). "The metabolism of n-butyl glycidyl ether in the rat and rabbit". Xenobiotica; the fate of foreign compounds in biological systems. 15 (7): 579–89. PMID 4049898. 
6. ↑ International Chemical Safety Card 0115