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271020

Sigma-Aldrich

1,3-Dioxolane

anhydrous, contains ~75 ppm BHT as inhibitor, 99.8%

Synonym(s):

Ethylene glycol methylene ether, Formaldehyde ethylene acetal

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About This Item

Empirical Formula (Hill Notation):
C3H6O2
CAS Number:
Molecular Weight:
74.08
Beilstein:
102453
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.21

grade

anhydrous

Quality Level

vapor density

2.6 (vs air)

vapor pressure

70 mmHg ( 20 °C)

Assay

99.8%

form

liquid

autoignition temp.

525 °F

contains

~75 ppm BHT as inhibitor

impurities

<0.003% water
<0.005% water (100 mL pkg)

evapn. residue

<0.0005%

refractive index

n20/D 1.401 (lit.)

bp

75-76 °C/1.013 hPa

mp

−95 °C (lit.)

density

1.06 g/mL at 25 °C (lit.)

SMILES string

C1COCO1

InChI

1S/C3H6O2/c1-2-5-3-4-1/h1-3H2

InChI key

WNXJIVFYUVYPPR-UHFFFAOYSA-N

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General description

1,3-dioxolane is a heterocyclic acetal that is commonly used as a green solvent in formulations and production processes. It is also used as a reactant in organic synthesis. Long-term storage of 1,3-dioxolane forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for peroxide formation.

Application

1,3-dioxolane can be used as a solvent:      
  • For the extraction of biodegradable poly(3-hydroxybutyrate) (PHB) from biomass.     
  • To produce stable dispersions of multiwalled carbon nanotubes (MWCNTs) for the synthesis of modified glassy carbon electrodes.
  • To synthesize copolymers (polyoxymethylene) by cationic copolymerization of 1,3,5-trioxane in the presence of maghnite-H+ as a catalyst.

It is also used as a reactant to prepare quasi-solid-state poly(1,3-dioxolane) electrolyte by Sc(OTf)3 catalyzed ring-opening polymerization reactions.
      

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Repr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

26.6 °F - closed cup

Flash Point(C)

-3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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1, 3-Dioxolane: A green solvent for the preparation of carbon nanotube-modified electrodes.
Moscoso R, et al.
Electrochemical Communications, 48, 69-72 (2014)
1, 3-Dioxolane, tetrahydrofuran, acetylacetone and dimethyl sulfoxide as solvents for non-aqueous vanadium acetylacetonate redox-flow-batteries.
Herr T, et al.
Electrochimica Acta, 113, 127-133 (2013)
Binary electrolyte based on tetra (ethylene glycol) dimethyl ether and 1, 3-dioxolane for lithium-sulfur battery.
Chang DR, et al.
Journal of Power Sources, 112(2), 452-460 (2002)
Vinodkumar Etacheri et al.
Langmuir : the ACS journal of surfaces and colloids, 28(14), 6175-6184 (2012-03-21)
The effect of 1,3-dioxolane (DOL) based electrolyte solutions (DOL/LiTFSI and DOL/LiTFSI-LiNO(3)) on the electrochemical performance and surface chemistry of silicon nanowire (SiNW) anodes was systematically investigated. SiNWs exhibited an exceptional electrochemical performance in DOL solutions in contrast to standard alkyl
Hideki Miyatake-Ondozabal et al.
Organic letters, 12(23), 5573-5575 (2010-11-12)
The biomimetic total synthesis of LL-Z1640-2 (3) is reported without the use of phenol protection. The aromatic unit was constructed via the transannular aromatization of macrocyclic triketo-ester 2, which in turn was synthesized by macrolactonization using an intramolecular trapping of

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