Description Reference
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
Product Name
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
Formula Weight
142.15
MOL File
5394-63-8.mol
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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)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

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

2,2,6-Trimethyl-4H-1,3-dioxin-4-one Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2,2,6-Trimethyl-4H-1,3-dioxin-4-one manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99%HPLC
Supply Ability
2000tons
Release date
2020-01-06
Hebei Chuanghai Biotechnology Co,.LTD
Product
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8
Price
US $100.00-50.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20
Henan Fengda Chemical Co., Ltd
Product
2,2,6-Trimethyl-4H-1,3-dioxin-4-one 5394-63-8
Price
US $6.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-03-28

5394-63-8, 2,2,6-Trimethyl-4H-1,3-dioxin-4-oneRelated Search:


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  • DIKETENE ACETONE ADDUCT
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  • 2,2,6-Trimethyl-4H-1,3-dioxin-4-one, 94%, contains up to 6% acetone
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