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HomeProduct name list2,2,6-Trimethyl-4H-1,3-dioxin-4-one

2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Synonym(s):Diketene acetone adduct;TMD

  • CAS NO.:5394-63-8
  • Empirical Formula: C7H10O3
  • Molecular Weight: 142.15
  • MDL number: MFCD00040468
  • EINECS: 226-403-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
2,2,6-Trimethyl-4H-1,3-dioxin-4-one Structural

What is 2,2,6-Trimethyl-4H-1,3-dioxin-4-one?

Chemical properties

Dark brown liquid

The Uses of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Diketene-Acetone Adduct can be used in place of diketene in many reactions. As a transportable form of diketene, it is especially important in those countries, where the transportation of diketene is not allowed or at least not desired.

The Uses of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

2,2,6-Trimethyl-1,3-dioxin-4-one is used in the synthesis of dihydropyrimininones as picomolar sodium iodide symporter inhibitors. It is also used in the synthesis of resorcinol amide Hsp90 Inhibitor AT13387. It is used in the synthesis of acetylketene by flash pyrolysis.

What are the applications of Application

2,2,6-Trimethyl-4H-1,3-dioxin-4-one generates unstable acetylketene together with acetone when heated above 120 ℃. Subsequent condensation with isocyanates, arylcyanates, or substituted cyanamides gives access to a wide range of 1,3-oxazine derivatives. Furthermore, diketene – acetone adduct can also be used for the preparation of a variety of compounds that are not accessible from diketene.

Chemical Reactivity

Diketene – acetone adduct (2,2,6-Trimethyl-4H-1,3-dioxin-4-one) can be regarded as a stabilized form of diketene. It can be safely transported and may conveniently be used instead of diketene in many reactions. For example, it reacts with alcohols and amines to yield acetoacetates and acetoacetamides, respectively. Diketene – acetone adduct generates unstable acetylketene together with acetone when heated above 120 ?C. Subsequent condensation with isocyanates, arylcyanates, or substituted cyanamides gives access to a wide range of 1,3-oxazine derivatives. Furthermore, diketene – acetone adduct can also be used for the preparation of a variety of compounds that are not accessible from diketene.

Properties of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Melting point: 12-13 °C(lit.)
Boiling point: ~275 °C(lit.)
Density  1.07 g/mL at 25 °C(lit.)
refractive index  n20/D 1.460(lit.)
Flash point: 67 °F
storage temp.  2-8°C
solubility  water: insoluble
form  Liquid
color  Dark brown
Water Solubility  practically insoluble
BRN  2408
Exposure limits ACGIH: TWA 250 ppm; STEL 500 ppm
OSHA: TWA 1000 ppm(2400 mg/m3)
NIOSH: IDLH 2500 ppm; TWA 250 ppm(590 mg/m3)
CAS DataBase Reference 5394-63-8(CAS DataBase Reference)

Safety information for 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

InChIKey XFRBXZCBOYNMJP-UHFFFAOYSA-N

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