ChemicalBook > CAS DataBase List > 2,2,6-Trimethyl-4H-1,3-dioxin-4-one

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

Description Reference

CAS No.5394-63-8
Chemical Name:2,2,6-Trimethyl-4H-1,3-dioxin-4-one
CBNumber:CB0412977
Molecular Formula:C7H10O3
Formula Weight:142.15
MOL File:5394-63-8.mol

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

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)
InChIKey XFRBXZCBOYNMJP-UHFFFAOYSA-N
CAS DataBase Reference 5394-63-8(CAS DataBase Reference)
UNSPSC Code 12352100
NACRES NA.22

Safety

Hazard Codes :F,Xi
Risk Statements :11-36/37/38-36
Safety Statements :16-26-27-36/37/39-9-33
RIDADR :UN 1993 3/PG 2
WGK Germany :3
HazardClass :3
PackingGroup :II
HS Code :29329995

NFPA 704:

	3
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H225-H319
Precautionary statements P210-P305+P351+P338

2,2,6-Trimethyl-4H-1,3-dioxin-4-one Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: 691380
Product name : 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
Purity: Arxada quality, ≥93.0% (GC)
Packaging: 1KG
Price: ₹37681.83
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 691380
Product name : 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
Purity: Arxada quality, ≥93.0% (GC)
Packaging: 25KG
Price: ₹322357.68
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 245100
Product name : 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
Purity: 95%
Packaging: 100G
Price: ₹6213.55
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: T1099
Product name : 2,2,6-Trimethyl-1,3-dioxin-4-one
Purity:
Packaging: 25ML
Price: ₹2500
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: T1099
Product name : 2,2,6-Trimethyl-1,3-dioxin-4-one
Purity:
Packaging: 500ML
Price: ₹14100
Updated: 2022/05/26
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2,2,6-Trimethyl-4H-1,3-dioxin-4-one Chemical Properties,Usage,Production

Description It is usually used as intermediate or raw material in the chemistry synthesis. For example, 2,2,6-Trimethyl-4H-1,3-dioxin-4-one can act as the starting material to produce N-alkenyl acetoacetamides through reaction with imines.¹ This substance can also be involved in the preparation of acetoacetamide derivatives, which result in the formation of the pyrrole amides via oxime of the acetoacetamides.² Moreover, this chemical may be introduced to promote the acetoacetylation of O-(hydroxypropyl)cellulose for generating O-(acetoxypropyl)cellulose.³ In addition, this chemical may be used to yield β-keto esters and β-ketoamides through the reaction with secondary or tertiary alcohols (including chiral ones) or primary or secondary amines.⁴
Reference
1. Dannibale, A.; Pesce, A.; Resta, S.; Trogolo, C., Reaction of 2,2,6-trimethyl-4H-1,3-dioxin-4-one with imines: An easy route to enamides. Tetrahedron Lett. 1996, 37, 7429-7432.
2. Huggins, M.; Barber, P.; Florian, D.; Howton, W., Short, Efficient Syntheses of Pyrrole -Amides. Synth. Commun. 2008, 38, 4226-4239.
3. Pawlowski, W. P.; Gilbert, R. D.; Fornes, R. E.; Purrington, S. T., ACETOACETYLATION OF O-(HYDROXYPROPYL)CELLULOSE BY 2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE. Carbohydr. Res. 1986, 156, 232-235.
4. Sridharan, V.; Ruiz, M.; Menendez, J. C., Mild and High-Yielding Synthesis of beta-Keto Esters and beta-Ketoamides. Synthesis 2010, 1053-1057.
Chemical Properties Dark brown liquid
Uses 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.
Uses 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.
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.