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

CAS No.
5394-63-8
Chemical Name:
2,2,6-Trimethyl-4H-1,3-dioxin-4-one
Synonyms
2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE;Diketton Acetone Adduct;2,2,6-TRIMETHYL-1,3-DIOXEN-4-ONE;TKD;2,2,6-TrimethyL;-4H-1,3-dioxin-4-one;DIKETE ACETONE ADDUCT;DIKETENE ACETONE ADDUCT;2,2,6-Trimethyl-4H-1,3-dioxin-;Trimethyl-(4H)-1,3-dioxin-4-one
CBNumber:
CB0412977
Molecular Formula:
C7H10O3
Molecular Weight:
142.15
MDL Number:
MFCD00040468
MOL File:
5394-63-8.mol
MSDS File:
SDS
Last updated:2024-03-28 13:39:29

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

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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS07
Signal word  Danger
Hazard statements  H225-H319
Precautionary statements  P210-P305+P351+P338
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

2,2,6-Trimethyl-4H-1,3-dioxin-4-one price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 691380 2,2,6-Trimethyl-4H-1,3-dioxin-4-one Lonza quality, ≥93.0% (GC) 5394-63-8 25kg $3240 2024-03-01 Buy
Sigma-Aldrich 691380 2,2,6-Trimethyl-4H-1,3-dioxin-4-one Lonza quality, ≥93.0% (GC) 5394-63-8 180kg $18930 2024-03-01 Buy
TCI Chemical T1099 2,2,6-Trimethyl-1,3-dioxin-4-one >95.0%(NMR) 5394-63-8 25mL $44 2024-03-01 Buy
TCI Chemical T1099 2,2,6-Trimethyl-1,3-dioxin-4-one >95.0%(NMR) 5394-63-8 500mL $191 2024-03-01 Buy
Alfa Aesar A14254 2,2,6-Trimethyl-1,3-dioxin-4-one, 94%, cont. up to ca 6% acetone 5394-63-8 25g $30.65 2024-03-01 Buy
Product number Packaging Price Buy
691380 25kg $3240 Buy
691380 180kg $18930 Buy
T1099 25mL $44 Buy
T1099 500mL $191 Buy
A14254 25g $30.65 Buy

2,2,6-Trimethyl-4H-1,3-dioxin-4-one Chemical Properties,Uses,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.

1694-31-1
67-64-1
5394-63-8
Synthesis of 2,2,6-Trimethyl-4H-1,3-dioxin-4-one from tert-Butyl acetoacetate and Acetone
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View Lastest Price from 2,2,6-Trimethyl-4H-1,3-dioxin-4-one manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
	2,2,6-Trimethyl-4H-1,3-dioxin-4-one pictures 2024-03-28 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
5394-63-8
US $6.00-1.00 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
2,2,6-Trimethyl-4H-1,3-dioxin-4-one pictures 2024-02-26 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
5394-63-8
US $0.00-0.00 / kg 1kg 97% Tons BTC Nantong Pharmaceuticals Technology Co.,Ltd
2,2,6-Trimethyl-4H-1,3-dioxin-4-one pictures 2023-08-31 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
5394-63-8
US $100.00 / drum 1drum 99 5000 Hebei Fengqiang Trading Co., LTD
DIKETENE ACETONE ADDUCT DIKETE ACETONE ADDUCT 2,6,6-TRIMETHYL-1,3-DIOXIN-4-ONE 2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE: 94%, CONT. UP TO CA 6% ACETONE 2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE, 94%, CONT. UP TO CA 6% ACE 2,2,6-trimethyl-1,3-dioxine-4H-one 2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE, TEC H., 85% 2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE 2,2,4-TRIMETHYL-6-KETO-1,3-DIOXIN 2,2,6-Trimethyl-1,3-dioxin-4-one, pract.,95% Trimethyl-(4H)-1,3-dioxin-4-one 2,2,6-Trimethyl-4H-1,3-dioxin-4-one, 90-95% 2,2,6-Trimethyl-4H-1,3-dioxin- 4H-1,3-Dioxin-4-one, 2,2,6-trimethyl- 2,2,6-trimethyl-1,3-dioxolenone 2,2,6-TriMethyl-4H-1,3-dioxin-4-one, 90-95% 100GR 2,2,4-Trimethyl-6-keto-1,3-dioxin Diketene Acetone Adduct 2,2,6-TRIMETHYL-1,3-DIOXINE-4-ONE FOR SY 2,2,6-Trimethyl-4H-1,3-dioxin-4-one, 94%, contains up to 6% acetone 2,2,6-Trimethyl-1,3-dioxine-4-one for synthesis TKD 2,2,6-TrimethyL -4H-1,3-dioxin-4-one 2,2,4-Trimethyl-6-keto-1,3-dioxine 2,2,6-TRIMETHYL-1,3-DIOXEN-4-ONE 2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE Diketton Acetone Adduct 212,6-Trinnethy1-4H-1,3- dioxin- 4-one 5394-63-8 Lactones Carbonyl Compounds Building Blocks Organic Building Blocks