| Identification | More | [Name]
2,2,6-Trimethyl-4H-1,3-dioxin-4-one | [CAS]
5394-63-8 | [Synonyms]
2,2,4-TRIMETHYL-6-KETO-1,3-DIOXIN
2,2,6-TRIMETHYL-1,3-DIOXEN-4-ONE
2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE
2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE
2,6,6-TRIMETHYL-1,3-DIOXIN-4-ONE
DIKETE ACETONE ADDUCT
DIKETENE ACETONE ADDUCT
TKD
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-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-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 | [EINECS(EC#)]
226-403-3 | [Molecular Formula]
C7H10O3 | [MDL Number]
MFCD00040468 | [Molecular Weight]
142.15 | [MOL File]
5394-63-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Dark brown liquid | [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.)
| [Fp ]
67 °F
| [storage temp. ]
2-8°C
| [solubility ]
water: insoluble | [form ]
Liquid | [color ]
Dark brown | [Water Solubility ]
practically insoluble | [Usage]
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. | [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) | [InChI]
InChI=1S/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3 | [InChIKey]
XFRBXZCBOYNMJP-UHFFFAOYSA-N | [SMILES]
O1C(C)=CC(=O)OC1(C)C | [CAS DataBase Reference]
5394-63-8(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Synthesis]
At 0°C, concentrated H2SO4 (0.530 mL) was added dropwise to a solution of tert-butyl 3-oxobutyrate (1.63 mL, 10.0 mmol, 1.00 eq) in acetone (10.0 mL) and Ac2O (10.0 mL). The mixture was heated for 5 hours, and the reaction mixture was added to 1M HCl. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with a saturated aqueous solution of NaHCO3 and brine. The mixture was dried over MgSO4, filtered to remove the solvent, and the residue was purified by column chromatography. The residue was purified by silica gel chromatography (0% to 30% ethyl acetate in hexane) to give 2,2,6-trimethyl-4H-1,3-dioxin-4-one. | [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]
- 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.
- Huggins, M.; Barber, P.; Florian, D.; Howton, W., Short, Efficient Syntheses of Pyrrole -Amides. Synth. Commun. 2008, 38, 4226-4239.
- 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.
- Sridharan, V.; Ruiz, M.; Menendez, J. C., Mild and High-Yielding Synthesis of beta-Keto Esters and beta-Ketoamides. Synthesis 2010, 1053-1057.
|
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H225-H319 | [Precautionary statements ]
P210-P305+P351+P338 | [Hazard Codes ]
F,Xi | [Risk Statements ]
R11:Highly Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R36:Irritating to the eyes. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S9:Keep container in a well-ventilated place .
S33:Take precautionary measures against static discharges . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29329995 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Eye Irrit. 2
Flam. Liq. 2 |
| Hazard Information | Back Directory | [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. | [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. |
| Spectrum Detail | Back Directory | [Spectrum Detail]
2,2,6-Trimethyl-4H-1,3-dioxin-4-one(5394-63-8)1HNMR
2,2,6-Trimethyl-4H-1,3-dioxin-4-one(5394-63-8)IR
2,2,6-Trimethyl-4H-1,3-dioxin-4-one(5394-63-8)Raman
2,2,6-Trimethyl-4H-1,3-dioxin-4-one(5394-63-8)FT-IR
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
2,2,6-Trimethyl-4H-1,3-dioxin-4-one, 90-95%(5394-63-8) | [Alfa Aesar]
2,2,6-Trimethyl-1,3-dioxin-4-one, 94%, cont. up to ca 6% acetone(5394-63-8) | [Sigma Aldrich]
5394-63-8(sigmaaldrich) | [TCI AMERICA]
2,2,6-Trimethyl-1,3-dioxin-4-one,>90.0%(GC)(5394-63-8) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|