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

2,2,6-Trimethyl-4H-1,3-dioxin-4-one - Names and Identifiers

Name	2,2,6-trimethyl-4H-1,3-dioxin-4-one
Synonyms	TKD DIKETE ACETONE ADDUCT DIKETENE ACETONE ADDUCT Diketton Acetone Adduct Diketene acetone adduct 2,6,6-TRIMETHYL-1,3-DIOXIN-4-ONE 2,2,4-trimethyl-6-keto-1,3-dioxin 2,2,6-trimethyl-1,3-dioxine-4H-one 2,2,6-trimethyl-4H-1,3-dioxin-4-one
CAS	5394-63-8
EINECS	226-403-3
InChI	InChI=1/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3
InChIKey	XFRBXZCBOYNMJP-UHFFFAOYSA-N

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

Molecular Formula	C7H10O3
Molar Mass	142.15
Density	1.07g/mLat 25°C(lit.)
Melting Point	12-13°C(lit.)
Boling Point	~275°C(lit.)
Flash Point	67°F
Water Solubility	practically insoluble
Solubility	water: insoluble
Vapor Presure	0.119mmHg at 25°C
Appearance	Liquid
Color	Dark brown
Exposure Limit	ACGIH: TWA 250 ppm; STEL 500 ppmOSHA: TWA 1000 ppm(2400 mg/m3)NIOSH: IDLH 2500 ppm; TWA 250 ppm(590 mg/m3)
BRN	2408
Storage Condition	2-8°C
Refractive Index	n20/D 1.460(lit.)

2,2,6-Trimethyl-4H-1,3-dioxin-4-one - Risk and Safety

Risk Codes	R11 - Highly Flammable R36/37/38 - Irritating to eyes, respiratory system and skin. R36 - Irritating to the eyes
Safety Description	S16 - Keep away from sources of ignition. 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.
UN IDs	UN 1993 3/PG 2
WGK Germany	3
HS Code	29329995
Hazard Class	3
Packing Group	II

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

Uses

2,2, 6-trimethyl-4H-1, 3-dioxin-4-one is a pharmaceutical intermediate, which can be made of 3-oxobutyrate tert-butyl ester and acetone are prepared by one-step reaction. 2,2, 6-trimethyl-4H-1, 3-dioxin-4-one can be used to prepare Apst's intermediate (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methanesulfonyl) ethylamine.

Preparation

At 0°C, concentrated H2SO4(0.530 mL) was added dropwise to acetone (10.0 mL) and Ac2O(10.0 mL) solutions of tert-butyl 3-oxobutyrate (1.63 mL,10.0 mmol,1.00eq). Heating for 5 hours, adding the reaction mixture to 1M HCl, extracting the water layer with ethyl acetate, washing the combined organic layer with saturated NaHCO3 aqueous solution and brine, drying with MgSO4, filtering, removing the solvent, and purifying the residue through the column. Purification by silica gel chromatography (0% to 30% hexane solution of ethyl acetate) to give 2,2, 6-trimethyl-4H-1, 3-dioxin-4-one.

Last Update：2024-04-10 22:29:15