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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
Assay:
99.8%
bp:
75-76 °C/1.013 hPa
vapor pressure:
70 mmHg ( 20 °C)
Pricing and availability is not currently available.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4581
SHBR7056
SHBR1536
SHBQ7906
SHBQ6674

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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)
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
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
Silvia Franchini et al.
European journal of medicinal chemistry, 45(9), 3740-3751 (2010-07-08)
A series of 1,3-dioxolane-based compounds incorporating a lactam (2-4) or imide (5-7) moiety was synthesized and the pharmacological profile at alpha(1)-adrenoceptor subtypes and 5-HT(1A) receptor was assessed through binding and functional experiments. Starting from the 2,2-diphenyl-1,3-dioxolane derivative 1, previously shown
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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