1,4-Dioxane

Not to be confused with 1,4-Dioxin.
"Dioxane" redirects here. For other uses, see Dioxane (compounds).

1,4-Dioxane
Chemical structure of dioxane
Chemical structure of dioxane
1,4-dioxane
1,4-dioxane
Names
Preferred IUPAC name
1,4-Dioxane
Systematic IUPAC name
1,4-Dioxacyclohexane
Other names
[1,4]Dioxane
p-Dioxane
[6]-crown-2
Diethylene dioxide
Diethylene ether
Dioxane solvent
Identifiers
3D model (JSmol)
102551
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.239 Edit this at Wikidata
EC Number
  • 204-661-8
KEGG
RTECS number
  • JG8225000
UNII
UN number 1165
  • InChI=1S/C4H8O2/c1-2-6-4-3-5-1/h1-4H2 checkY
    Key: RYHBNJHYFVUHQT-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O2/c1-2-6-4-3-5-1/h1-4H2
    Key: RYHBNJHYFVUHQT-UHFFFAOYAN
  • O1CCOCC1
Properties
C4H8O2
Molar mass 88.106 g·mol−1
Appearance Colorless liquid[1]
Odor Mild, diethyl ether-like[1]
Density 1.033 g/mL
Melting point 11.8 °C (53.2 °F; 284.9 K)
Boiling point 101.1 °C (214.0 °F; 374.2 K)
Miscible
Vapor pressure 29 mmHg (20 °C)[1]
−52.16·10−6 cm3/mol
Thermochemistry
196.6 J/K·mol
−354 kJ/mol
−2363 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Suspected human carcinogen[1]
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225, H302, H305, H315, H319, H332, H336, H351, H370, H372, H373
P201, P202, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P281, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
3
1
Flash point 12 °C (54 °F; 285 K)
180 °C (356 °F; 453 K)
Explosive limits 2.0–22%[1]
Lethal dose or concentration (LD, LC):
  • 5 g/kg (mouse, oral)
  • 4 g/kg (rat, oral)
  • 3 g/kg (guinea pig, oral)
  • 7.6 g/kg (rabbit, dermal)
  • 10,109 ppm (mouse, 2 hr)
  • 12,568 ppm (rat, 2 hr)[2]
1000–3000 ppm (guinea pig, 3 hr)

12,022 ppm (cat, 7 hr)
2085 ppm (mouse, 8 hr)[2]

NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 100 ppm (360 mg/m3) [skin][1]
REL (Recommended)
 Ca C 1 ppm (3.6 mg/m3) [30-minute][1]
IDLH (Immediate danger)
 Ca [500 ppm][1]
Related compounds
Related compounds
 Oxane
Trioxane
Tetroxane
Pentoxane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,4-Dioxane (/daɪˈɒkseɪn/) is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.

Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminium containers.[3]

  1. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0237". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Dioxane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Wisconsin Department of Health Services (2013) 1,4-Dioxane Fact Sheet Archived 16 October 2020 at the Wayback Machine. Publication 00514. Accessed 2016-11-12.