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1,3-Dioxolane

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1,3-Dioxolane Basic information
1,3-Dioxolane Chemical Properties
  • Melting point:−95 °C(lit.)
  • Boiling point:74-75 °F(lit.)
  • Density 1.06 g/mL at 25 °C(lit.)
  • vapor density 2.6 (vs air)
  • vapor pressure 70 mm Hg ( 20 °C)
  • refractive index n20/D 1.401(lit.)
  • Flash point:35 °F
  • storage temp. Refrigerator
  • solubility 1000g/l soluble
  • form Liquid
  • color White to off-white
  • explosive limit2.1-20.5%(V)
  • Water Solubility SOLUBLE
  • BRN 102453
  • Stability:Below 4°C
  • CAS DataBase Reference646-06-0(CAS DataBase Reference)
  • NIST Chemistry Reference1,3-Dioxolane(646-06-0)
  • EPA Substance Registry System1,3-Dioxolane(646-06-0)
Safety Information
  • Hazard Codes F
  • Risk Statements 11
  • Safety Statements 16
  • RIDADR UN 1166 3/PG 2
  • WGK Germany 1
  • RTECS JH6760000
  • Autoignition Temperature525 °F
  • TSCA Yes
  • HazardClass 3
  • PackingGroup II
  • HS Code 29329970
  • Hazardous Substances Data646-06-0(Hazardous Substances Data)
  • ToxicityLD50 orally in Rabbit: 3000 mg/kg LD50 dermal Rabbit 9074 mg/kg
MSDS
1,3-Dioxolane Usage And Synthesis
  • Chemical PropertiesColourless Liquid
  • Uses1,3-Dioxolane is an intermediate for the preparation of Acyclovir (A192400). Also, 1,3-Dioxolane is used in the synthesis of new Vandetanib (V097100) analogs.
  • UsesIntermediate for the preparation of Acyclovir-d4
  • Uses1,3-Dioxolane is used as an intermediate inorganic synthesis.
  • DefinitionChEBI: A cyclic acetal that is pentane in which the carbon atoms at positions 1 and 3 are replaced by oxygen atoms respectively.
  • General DescriptionA clear colorless liquid. Flash point 35°F. Slightly denser than water. Vapors heavier than air.
  • Air & Water ReactionsHighly flammable. When exposed to air 1,3-Dioxolane undergoes autooxidation with formation of peroxides. In the distillation process peroxides will concentrate causing violent explosion. Soluble in water.
  • Reactivity ProfileEthers, such as 1,3-Dioxolane, can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
  • Health HazardInhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.
  • Health HazardThe acute inhalation and oral toxicity of1,3-dioxolane is low in test animals. Thevapor is irritant to eyes and respiratory tract.Application of the liquid produced severeirritation in rabbits’ eyes and mild action onthe animals’ skin. The information on thetoxicity of this compound in humans is notknown.
    The inhalation LC50 value of 4-hour exposurein rats is in the range of 20,000 mg/m3,and the oral LD50 is 3000 mg/kg (NIOSH1986).
  • Fire HazardHIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
  • Industrial uses1,3-Dioxolane is used to dissolve a wide spectrum of polymeric materials such as acrylates, alkyds, cellulosics, epoxies, polycarbonates, polyesters, urethanes, and vinyl resins. In many cases, 1,3-dioxolane solvent can replace the chlorinated solvents that were used previously to dissolve many of these polymers. The excellent solvency of 1,3-dioxolane for polymeric compositions makes this cyclic ether a valuable component in paint remover formulations. 1,3-Dioxolane is used to treat polyester fibers for improved dye retention, application of cross-linking agents to cellulosic fibers, and bonding of acrylonitrile polymers. 1,3-Dioxolane is used in metal working and electroplating formulations, as a complexing solvent for organometallic and inorganic salts, and in the preparation of lithium battery electrolyte solutions. 1,3-Dioxolane is a valuable reactant in the polymerization reactions to produce polyacetals. Polymerization reactions of dioxolane with itself or with aldehydes and ethers are catalyzed by a Lewis acid to yield the polyacetal polymers. The methylene group (CH2) bonded to the two oxygen atoms in dioxolane is susceptible to radical abstraction of a hydrogen atom and the resultant dioxolane radical species can be added across various double bond configurations.
  • Safety ProfileModerately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact and inhalation. A shin and severe eye irritant. Mutation data reported. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizers. Used in lithium batteries. Potentially explosive reaction with lithium perchlorate. When heated to decomposition it emits acrid smoke and irritating fumes.
  • Purification MethodsDry it with solid NaOH, KOH or CaSO4, and distil it from sodium or sodium amalgam. Barker et al. [J Chem Soc 802 1959] heated 34mL of dioxalane under reflux with 3g of PbO2 for 2hours, then cooled and filtered. After adding xylene (40mL) and PbO2 (2g) to the filtrate, the mixture is fractionally distilled. Addition of xylene (20mL) and sodium wire to the main fraction (b 70-71o) led to a vigorous reaction, following which the mixture was again fractionally distilled. Xylene and sodium additions are made to the main fraction (b 73-74o) before it is finally distilled. [Beilstein 19/1 V 6.]
1,3-Dioxolane Preparation Products And Raw materials
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