n-Butyl glycidyl ether

n-Butyl glycidyl ether
Names
	Preferred IUPAC name 2-(Butoxymethyl)oxirane
	Other names 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 (JSmol)	Interactive image;
ChemSpider	16149;
ECHA InfoCard	100.017.616
PubChem CID	17049;
RTECS number	TX4200000;
UNII	M03777A62S ;
UN number	1993
CompTox Dashboard (EPA)	DTXSID9024691 ;
	InChI InChI=1S/C7H14O2/c1-2-3-4-8-5-7-6-9-7/h7H,2-6H2,1H3 Key: YSUQLAYJZDEMOT-UHFFFAOYSA-N;
	SMILES CCCCOCC1CO1;
Properties
Chemical formula	C7H14O2
Molar mass	130.187 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]
	NIOSH (US health exposure limits):
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 to form a halohydrin. This is 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]

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References

NIOSH Pocket Guide to Chemical Hazards. "#0081". National Institute for Occupational Safety and Health (NIOSH).
"Propane, 1-Butoxy-2,3-epoxy". CDC/NIOSH.
"{{{2}}}". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
CID 17049 from PubChem
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. 15 (7): 579–89. doi:10.3109/00498258509045887. PMID 4049898.
International Chemical Safety Card 0115

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[NPG-1] NIOSH Pocket Guide to Chemical Hazards. "#0081". National Institute for Occupational Safety and Health (NIOSH).

[RTECS-2] "Propane, 1-Butoxy-2,3-epoxy". CDC/NIOSH.

[IDLH-3] "{{{2}}}". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PubChem-4] 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. 15 (7): 579–89. doi:10.3109/00498258509045887. PMID 4049898.

[ICSC-6] International Chemical Safety Card 0115