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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:
646-06-0
Molecular Weight:
74.08
Beilstein:
102453
EC Number:
211-463-5
MDL number:
MFCD00003207
UNSPSC Code:
12352005
PubChem Substance ID:
57648184
NACRES:
NA.21

grade

anhydrous

Quality Level

100

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

H225,H319,H360

Hazard Classifications

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

WGK

WGK 1

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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)
1, 3-Dioxolane: A green solvent for the preparation of carbon nanotube-modified electrodes.
Moscoso R, et al.
Electrochemical Communications, 48, 69-72 (2014)
Lukas J Goossen et al.
The Journal of organic chemistry, 73(21), 8631-8634 (2008-10-23)
An efficient synthesis of the angiotensin II receptor antagonist telmisartan is presented involving a decarboxylative cross-coupling of isopropyl phthalate (1) with 2-(4-chlorophenyl)-1,3-dioxolane (2c) as the key step (85% yield). The benzimidazole moiety is constructed regioselectively via a reductive amination-condensation sequence
Dong Zhou et al.
Nuclear medicine and biology, 35(6), 655-663 (2008-08-06)
Progesterone receptors (PRs) are present in many breast tumors, and their levels are increased by certain endocrine therapies. They can be used as targets for diagnostic imaging and radiotherapy. 16alpha,17alpha-[(R)-1'-alpha-(5-[(76)Br]Bromofurylmethylidene)dioxyl]-21-hydroxy-19-norpregn-4-ene-3,20-dione ([(76)Br]16alpha,17alpha-[(R)-1'-alpha-(5-bromofurylmethylidene)dioxyl]-21-hydroxy-19-norpregn-4-ene-3,20-dione (3)), a PR ligand with relative binding affinity (RBA)=65
One-step synthesis of 2-alkyl-dioxolanes from ethylene glycol and syngas.
Xiao-Bing Fan et al.
ChemSusChem, 2(10), 941-943 (2009-10-01)
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