N-Butyl glycidyl ether

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.^[4]

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 Y
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

Synthesis

n-Butyl alcohol and epichlorohydrin react to form a halohydrin. This is followed by a caustic dehydrochlorination, to form n-butyl glycidyl ether.^[5]

Metabolism

n-Butyl glycidyl ether is metabolized renally to butoxyacetic acid, 3-butoxy-2-hydroxypropionic acid and 3-butoxy-2-acetylaminopropionic acid.^[5][6]

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.^[7]

Uses

As an Epoxy modifier it is classed as an epoxy reactive diluent.^[8] It is also used to synthesize other molecules.^[9] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[10][11] It has been used to simultaneously increase cryogenic strength, ductility and impact resistance of epoxy resins.^[12]