505-22-6

Basic information

• Product Name: 1,3-DIOXANE
• Synonyms: 1,3-Dioxacyclohexane;1,3-Propanediol formal;1,3-propanediolformal;dihydro-m-dioxi;m-Dioxin, dihydro-;meta-dioxane;trimethyleneglycolmethyleneether;1,3-DIOXANE
• CAS NO: 505-22-6
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.11
• EINECS: 208-005-1
• Product Categories: Dioxanes;Dioxanes & Dioxolanes
• Mol File: 505-22-6.mol

Chemical Properties

• Melting Point: −45 °C(lit.)
• Boiling Point: 105-106 °C(lit.)
• Flash Point: 59 °F
• Appearance: /
• Density: 1.032 g/mL at 25 °C(lit.)
• Vapor Pressure: 34.3mmHg at 25°C
• Refractive Index: n20/D 1.418(lit.)
• Storage Temp.: Flammables area
• Water Solubility: Fully miscible in water.
• Stability: Stable. Flammable. Incompatible with oxidizing agents. May form explosive peroxides in contact with the air - store under inert
• BRN: 102532
• CAS DataBase Reference: 1,3-DIOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIOXANE(505-22-6)
• EPA Substance Registry System: 1,3-DIOXANE(505-22-6)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/21/22
• Safety Statements: 16
• RIDADR: UN 1165 3/PG 2
• WGK Germany: 3
• RTECS: JG8224000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 505-22-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Dioxane is used as a solvent for the synthesis of various pharmaceutical compounds, such as 8and 9-membered dioxazocines and dioxazonines. Its ability to dissolve a wide range of substances makes it a valuable component in the development and production of these complex molecules.
Used in Chemical Synthesis:
1,3-Dioxane is utilized as a solvent in various chemical synthesis processes due to its polarity and low reactivity. This allows for the efficient and controlled reaction of different compounds, leading to the formation of desired products with minimal side reactions.
Used in Industrial Applications:
In the industrial sector, 1,3-dioxane is employed as a stabilizer and a component in the production of various chemicals, such as resins, plastics, and adhesives. Its versatility and compatibility with a range of materials make it a valuable asset in the manufacturing process.
Used in Laboratory Settings:
Due to its properties as a solvent, 1,3-dioxane is commonly used in laboratory settings for the extraction and purification of various compounds. Its ability to dissolve a wide range of substances makes it an essential tool in research and development.

Air & Water Reactions

Highly flammable. Can form dangerous peroxides when exposed to air. Water soluble.

Reactivity Profile

1,3-DIOXANE is sensitive to heat. 1,3-DIOXANE can react with oxidizers.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 1,3-DIOXANE emits acrid smoke and fumes.

Fire Hazard

1,3-DIOXANE is flammable.

Purification Methods

Dry the dioxane with sodium and fractionally distil it. [Beilstein 19/1 V 11.]

InChI:InChI=1/C4H8O2/c1-2-5-4-6-3-1/h1-4H2

Upstream product

• 100-97-0 hexamethylenetetramine 
• 504-63-2 trimethyleneglycol 
• 50-00-0 formaldehyd 
• 20757-83-9 [1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide 
• 872-98-0 5,5-dimethyl-1,3-dioxane 
• 76508-46-8 2-ethoxy-1,3-dioxane 
• 617-86-7 triethylsilane 
• 1825-14-5 pentane-1,3-diol 
• 110-88-3 1,3,5-Trioxan 
• 74-85-1 ethene 
• 64-19-7 acetic acid 
• 64-18-6 formic acid 
• 135475-61-5 N-(4'-chloro-2'-fluoro-5'-formylphenyl)-3-(trifluoromethyl)glutarimide 
• 112-31-2 caprinaldehyde 

Downstream Products

• 17841-46-2 (n-pr)3Si(Ome) 
• 17980-36-8 1-methoxy-3-(triethylsiloxy)-propane 
• 96517-53-2 4-(1,3-dioxane-2-yl)quinaldine 
• 96517-51-0 4-(1,3-dioxane-4-yl)quinaldine 
• 107-46-0 Hexamethyldisiloxane 
• 17887-80-8 1,3-bis(trimethylsiloxy)propane 
• 97290-74-9 1,3-bis(iodomethoxy)propane 
• 74858-18-7 diphenyl <(3-chloropropoxy)methyl>phosphonate 
• 872-98-0 5,5-dimethyl-1,3-dioxane 
• 71-23-8 propan-1-ol 
• 1589-49-7 methoxypropanol 
• 60833-52-5 iodo(iodomethoxy)methane 
• 112539-38-5 iodomethyl 3-iodopropyl ether 
• 110-74-7 propyl methanoate 

Relevant articles and documents

Biomass alcoholysis method for petroleum-based plastic POM

The invention discloses a biomass alcoholysis method for petroleum-based plastic POM. According to the method, simple biomass derivative alcohol and the petroleum-based plastic POM are allowed to generate a cyclic acetal product through dehydration condensation under catalytic conditions; low reaction cost and high added value are realized, and only water is byproduced and is easy to separate; and an obtained product has high added value, can be used for preparing organic solvents such as lignin and chromatographic analysis solvents, metal surface treatment agents or medical intermediates and monomers, realizes green, efficient and low-cost recovery, and has a high practical application value.

Efficient Plastic Waste Recycling to Value-Added Products by Integrated Biomass Processing

The industrial production of polymeric materials is continuously increasing, but sustainable concepts directing towards a circular economy remain rather elusive. The present investigation focuses on the recycling of polyoxymethylene polymers, facilitated through combined catalytic processing of polymer waste and biomass-derived diols. The integrated concept enables the production of value-added cyclic acetals, which can flexibly function as solvents, fuel additives, pharmaceutical intermediates, and even monomeric materials for polymerization reactions. Based on this approach, an open-loop recycling of these waste materials can be envisaged in which the carbon content of the polymer waste is efficiently utilized as a C1 building block, paving the way to unprecedented possibilities within a circular economy of polyoxymethylene polymers.

Ruthenium-Catalyzed Synthesis of Cyclic and Linear Acetals by the Combined Utilization of CO2, H2, and Biomass Derived Diols

Herein a transition-metal catalyst system for the selective synthesis of cyclic and linear acetals from the combined utilization of carbon dioxide, molecular hydrogen, and biomass derived diols is presented. Detailed investigations on the substrate scope enabled the selectivity of the reaction to be largely guided and demonstrated the possibility of integrating a broad variety of substrate molecules. This approach allowed a change between the favored formation of cyclic acetals and linear acetals, originating from the bridging of two diols with a carbon-dioxide based methylene unit. This new synthesis option paves the way to novel fuels, solvents, or polymer building blocks, by the recently established “bio-hybrid” approach of integrating renewable energy, carbon dioxide, and biomass in a direct catalytic transformation.

Selective Conversion of Carbon Dioxide to Formaldehyde via a Bis(silyl)acetal: Incorporation of Isotopically Labeled C1 Moieties Derived from Carbon Dioxide into Organic Molecules

The conversion of carbon dioxide to formaldehyde is a transformation that is of considerable significance in view of the fact that formaldehyde is a widely used chemical, but this conversion is challenging because CO2 is resistant to chemical transformations. Therefore, we report here that formaldehyde can be readily obtained from CO2 at room temperature via the bis(silyl)acetal, H2C(OSiPh3)2. Specifically, formaldehyde is released from H2C(OSiPh3)2 upon treatment with CsF at room temperature. H2C(OSiPh3)2 thus serves as a formaldehyde surrogate and provides a means to incorporate CHx (x = 1 or 2) moieties into organic molecules. Isotopologues of H2C(OSiPh3)2 may also be synthesized, thereby providing a convenient means to use CO2 as a source of isotopic labels in organic molecules.

Dimethyl sulfoxide as a "methylene" source: Ru(ii) photo-catalysed facile synthesis of acetals from alcohols

Acetals are important molecules with versatile reactivity and uses. For the first time a simple photo-catalysed facile synthesis of formaldehyde acetals is documented herein upon the reaction of alcohols with dimethyl sulfoxide under very mild conditions in the presence of air. The reactions require only 1 mol% of RuII(bpy)3Cl2 photocatalyst under blue LED irradiation (λ = 445 nm) to give good to excellent yields of the corresponding acetal products. Here DMSO acts as a "methylene" source.

MANUFACTURE OF 1,3-PROPANEDIOL ESTERS

Disclosed is a process for manufacturing an ester of 1,3-propanediol, comprising, contacting at a temperature of about 0 DEG C. to about 250 DEG C., ethylene, formaldehyde or a form of formaldehyde, a carboxylic acid, and a compound of the formula MZn.Qt, wherein: M is a zirconium[IV], cobalt[II], vanadium[IV], bismuth[II], tin[II], a rare earth metal, scandium or yttrium; n is the oxidation state of M; at least one of Z is an anion of the formula R1SO3- or R1CO2-, wherein R1 is hydrocarbyl or substituted hydrocarbyl containing 1 to 20 carbon atoms or part of a polymer, and the remainder of Z is oxo or one or more monovalent anions; Q is a neutral ligand; and t is 0 or an integer of 1 to 12.

C1-C6-epothilone fragments and process for the production of C1-C6-fragments of epothilones and derivatives thereof

This invention describes C1-C6-epothilone fragments and an efficient process for the production of C1-C6-fragments of epothilones and derivatives thereof.

Montmorillonite, an efficient catalyst for the preparation of dialkoxymethanes

The reaction of various alcohols with paraformaldehyde in presence of montmorillonite to give dialkoxymethanes (2a-g) in very good yield is described.

Herbicidal glutarimides

This invention relates to glutarimide compounds exhibiting herbicidal activity having the structure STR1 wherein A is carbonyl, thiocarbonyl or methylene, A1 is carbonyl or methylene, Q is O or (CH2)n where n is 0 or 1, D is CH or N and R, R1, R2, T, X, Y and Z are as defined within, compositions containing these compounds and methods of using these compounds as herbicides and algicides.

Transformation of 1,3-, 1,4- and 1,5-diols over perfluorinated resinsulfonic acid (Nafion-H)

The transformations of 1,3-, 1,4- and 1,5-diols over perfluorinated resinsulfonic acids (Nafion-H) were studied and correlations were examined between the structure of the investigated diols, the possible transformation directions and the catalytic properties of Nafion-H. Comparisons were also made between the catalytic properties of Nafion-H and zeolites. The characteristic transformations of 1,3-diols depend on their structure. 1,3-Propanediol undergoes dehydration via 1,2-elimination and yields oligomers via intermolecular dehydration. 1,3-Diols with an alkyl substituent on the carbon between those bearing the OH groups undergo 1,2-elimination yielding unsaturated alcohols and dienes, and give carbonyl compounds via the loss of water and hydride shifts analogous to the pinacol rearrangement. The strong acidity of Nafion-H and the lack of strong basic sites are advantageous for the latter reaction. 1,3-Diols with two substituents at this position mainly yield fragmentation products. Stereoselective cyclodehydration to the corresponding oxacycloalkanes is the characteristic transformation of 1,4- and 1,5-diols over Nafion-H.