Dioxane

Other Names:

1,4-Dioxane

p-Dioxane

General Information:

Structure:

CAS Number: 123-91-1

Molecular Weight: 88.11 g/mol

Appearance: Colorless liquid

Melting Point: 10-12 C

Boiling Point: 100-102 C

Density: 1.034 g/mL

Dioxane is a common aprotic solvent in organic chemistry. It is an ethereal solvent which is miscible with water. Dioxane can sometimes be a useful alternative to THF when a higher boiling point is desired. Commercially available 4M HCl in dioxane is one of the most frequently encountered applications of dioxane as a solvent. The use of 4M HCl in dioxane is common for boc deprotections.

Common Uses:

Solvent for reactions

Procedure excerpt:

. . . the SM (1.0 equiv), KOAc (3.0 equiv), bis(pinacolato)diboron (2.0 equiv), tricyclohexylphosphine (0.8 equiv), and Pd2(dba)3 (0.2 equiv) in dioxane (0.06 M) was . . .

[full procedure]

Safety:

Dioxane is irritating to the eyes and respiratory tract but has a low acute toxicity. It is considered by the EPA to be a probable human carcinogen. Dioxane is a flammable liquid.

References:

1) Patent Reference: WO2010026121, page 36, (3.6 MB)

2) Wikipedia: 1,4-Dioxane (link)

3) www.sigmaaldrich.com: 1,4-Dioxane (link)