EMAIL THIS PAGE TO A FRIEND
296309 Sigma-Aldrich

1,4-Dioxane

anhydrous, 99.8%

Synonym: Diethylene oxide, Dioxane

  • CAS Number 123-91-1

  • Empirical Formula (Hill Notation) C4H8O2

  • Molecular Weight 88.11

  •  Beilstein/REAXYS Number 102551

  •  EC Number 204-661-8

  •  MDL number MFCD00006571

  •  PubChem Substance ID 57648388

Purchase

Properties

Related Categories Anhydrous, Anhydrous Solvents, Returnable Containers, Solvent Bottles, Solvent Packaging Options,
grade   anhydrous
vapor density   3 (vs air)
vapor pressure   27 mmHg ( 20 °C)
  40 mmHg ( 25 °C)
InChI Key   RYHBNJHYFVUHQT-UHFFFAOYSA-N
assay   99.8%
form   liquid
autoignition temp.   356 °F
expl. lim.   22 %
impurities   <0.003% water
  <0.005% water (100 mL pkg)
evapn. residue   <0.0003%
refractive index   n20/D 1.422 (lit.)
bp   100-102 °C (lit.)
mp   10-12 °C (lit.)
density   1.034 g/mL at 25 °C (lit.)

Description

Application

1,4-Dioxane may undergo nickel-catalyzed oxidative arylation with arylboronic acids to form α-arylated ethers.
It may be used as a solvent to synthesize:
•  (Chloromethyl)dimethylphenylsilane from chloro(chloromethyl)dimethylsilane via zinc-catalyzed substitution reaction with phenylmagnesium bromide.
• N-(2,2,2-trifluoro-1-hydroxyethyl)-acetamide from 2,2,2-trifluoro-1-methoxyethanol and acetamide.

Packaging

1, 6×1, 2 L in Sure/Seal™

View returnable container options.

100, 12×100 mL in Sure/Seal™

18, 200 L in Pure-Pac™ 1

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Supplemental Hazard Statements 
May form explosive peroxides., Repeated exposure may cause skin dryness or cracking.
RIDADR 
UN1165 - class 3 - PG 2 - Dioxane
WGK Germany 
2
RTECS 
JG8225000
Flash Point(F) 
53.6 °F
Flash Point(C) 
12 °C

Documents

Certificate of Analysis

Please Enter a Lot Number

Certificate of Origin

Please Enter a Lot Number

Dispensette™ S
Protocols & Articles

Articles

A Convenient and Expeditious Synthesis of 3-(N-Substituted) Aminocoumarins via Palladium-Catalyzed Buchwald-Hartwig Coupling Reaction

Decarboxylative coupling of sp-sp2 carbons is possible by palladium catalyst. Employing propiolic acid as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and th...
Keywords: Chromatography, Flash chromatography

A Versatile Method for Suzuki Cross-Coupling Reactions of Nitrogen Heterocycles

In air, Pd(OAc)2 (9.1 mg, 1.141 mmol), PCy3 (22.4 mg, 1.181 mmol), and K3PO4�H2O (276 mg, 1.21 mmol) are added to a reaction vessel equipped with a stir bar. The vessel is sealed with a septum and pu...
Keywords: Chromatography, Column chromatography

Anhydrous Solvents for Coupling Reactions

Due to the sensitivity to air and moisture, coupling reactions often require relatively low air and water conditions to initiate the reaction. Therefore, the use of anhydrous solvents is highly recom...
Keywords: Coupling reactions, Cross couplings, Negishi Coupling, Solvents

Anhydrous Solvents for Organic and Organometallic Chemistry

Many well-known reactions require water-free conditions to initiate or complete the reaction. Failure to include anhydrous solvents can result in low product yield or reaction failure. As the market ...
Keywords: Acylations, Alkylations, Electrophilic aromatic substitution, Formylations, Grignard Reaction, Solvents, Substitutions, Vilsmeier-Haack reaction

Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions

Good to excellent yields�of aryl trifluoromethyl sulfides, which are an important class of compounds in both the pharmaceutical and agrochemical areas, can be achieved under mild conditions by the Pd...
Keywords: Agrochemicals, Catalysis, Pharmaceutical

Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give...
Keywords: Catalysis, Chromatography, Column chromatography

Palladium-Catalyzed Hydroxylation of Aryl and Heteroaryl Halides Enabled by the Use of a Palladacycle Precatalyst

A method for the hydroxylation of aryl and heteroaryl halides, promoted by a catalyst based on a biarylphosphine ligand tBuBrettPhos (L5) and its corresponding palladium precatalyst (1), is described...
Keywords: Chromatography, Cross couplings, Flash chromatography, Hydroxylations, Ligands

Palladium-catalyzed coupling of functionalized primary and secondary amines with aryl and heteroaryl halides: two ligands suffice in most cases

We report our studies on the use of two catalyst systems, based on the ligands BrettPhos and RuPhos, which provide the widest scope for Pd-catalyzed C-N cross-coupling reactions to date. Often low ca...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Ligands, Pharmaceutical

Pd(PhCN)2Cl2/P(t-Bu)3: A Versatile Catalyst for Sonogashira Reactions of Aryl Bromides at Room Temperature

The Suzuki-Miyaura cross-coupling of unprotected, nitrogen-rich heterocycles using precatalysts P1 or P2 is reported. The procedure allows for the reaction of variously substituted indazole, benzimid...
Keywords: Catalysis, Chromatography, Column chromatography, Coupling reactions, Cross couplings

Pd-PEPPSI-IPent: An Active, Sterically Demanding Cross-Coupling Catalyst and Its Application in the Synthesis of Tetra-Ortho- Substituted Biaryls-

The halogenated 1H-1,2,4-triazole glycosides 6-11 were synthesized by BF3-activated glycosylation of 3(5)-chloro-1,2,4- triazole (2), 3,5-dichloro-1,2,4-triazole (3), 3,5-dibromo-1,2,4-triazole (4), ...
Keywords: Arylations, Catalysis, Coupling reactions, Cross couplings, Glycosylations, Purification, Separation

Pressure-Temperature Calculator for Solvents

*Calculations provide estimated results based on Antoine's Coefficients and their associated temperature range values. Antoine's Coefficients were obtained from the National Institute of Standards an...

Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation

A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required h...
Keywords: Catalysis, Chromatography, Flash chromatography, Thin layer chromatography

TLC Analysis of Phosphates on TLC pre-coated plate Cellulose

From our library of Articles, Sigma-Aldrich presents TLC Analysis of Phosphates on TLC pre-coated plate Cellulose
Keywords: Thin layer chromatography

The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides

A series of N-heterocyclic carbene catalysts (see picture) were prepared and evaluated in the Suzuki-Miyaura reaction. A variety of sterically encumbered tetra-ortho-substituted biaryl products were ...
Keywords: Chromatography, Flash chromatography

Related Content

Pressure-Temperature Nomograph Interactive Tool

Use the interactive controls above to simplify calculations and improve the efficiency of your distillation or evaporation requirements.
Keywords: Evaporation, Vaporization

Properties of Solvents Table

The table below presents the physical characteristics of common solvents. Easily reference or compare solvent properties like boiling point, density, and refractive index all from one list.
Keywords: Gas chromatography, Green chemistry, High performance liquid chromatography, Melting, Solvents

Peer-Reviewed Papers
15

References

Related Products

also commonly purchased with this product

Product #

Description

Add to Cart

270997 Dichloromethane, anhydrous, ≥99.8%, contains 40-150 ppm amylene as stabilizer
271012 N,N-Dimethylacetamide, anhydrous, 99.8%
186562 Tetrahydrofuran, anhydrous, contains 250 ppm BHT as inhibitor, ≥99.9%
227056 N,N-Dimethylformamide, anhydrous, 99.8%

recommended

Product #

Description

Add to Cart

Z683299 XPell indicating pellets for peroxides prevention, CE for organic solvents

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?