2,2,6-Trimethyl-4h-1,3-Dioxin-4-One

English synonyms

DikettonAcetoneAdduct;DIKETENEACETONEADDUCT;DIKETEACETONEADDUCT;
2,6,6-TRIMETHYL-1,3-DIOXIN-4-ONE;
2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE:94%,CONT.UPTOCChemicalbookA6%ACETONE;
2,2,6-TRIMETHYL-1,3-DIOXIN-4-ONE,94%,CONT.UPTOCA6%ACE;
2,2,6-trimethyl-1,3-dioxine-4H-one;
2,2,6-TRIMETHYL-4H-1,3-DIOXIN-4-ONE,TECH.,85%

CAS number

5394-63-8

Molecular formula

C7H1003

Molecular weight

142.15

EINECS number

226-403-3

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 conditions

2-8℃

Solubility

Water: Insoluble

Form

Liquid

Color

Dark brown

Water solubility

practically insoluble

BRN

2408

Exposure limit

ACGIH:TWA 250 ppm;STEL 500 ppm
OSHA:TWA 1000 ppm(2400 mg/m3)
NIOSH:IDLH 2500 ppm;TWA 250 ppm(590 mg/m3)

InChl

InChl=1S/C7H1003/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3

InChlKey

XFRBXZCBOYNMJP-UHFFFAOYSA-N

SMILES

01C(C)=CC(=O)OC1(C)C

Chemical Properties

Dark brown liquid (normal temperature and pressure), can be hydrolyzed or alcoholyzed with water or alcohol compounds at high temperature to obtain the corresponding product acid or ester.

Uses

2,2,6-Trimethyl-4H-1,3-dioxin-4-one is a pharmaceutical intermediate, which can be prepared by one-step reaction from tert-butyl 3-oxobutyrate and acetone as raw materials.
2,2Chemicalbook,6-Trimethyl-4H-1,3-dioxin-4-one can be used to prepare the intermediate (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine of Apremilast.

Preparation

At 0°C, add concentrated H2SO4 (0.530mL) dropwise to a solution of tert-butyl 3-oxobutyrate (1.63mL, 10.0mmol, 1.00eq) in acetone (10.0mL) and Ac2O (10.0mL). After heating for 5 hours,
the reaction mixture was added to 1M HCl, the aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with saturated aqueous NaHCO3 and brine,
dried over MgSO4, filtered, the solvent was removed, and the residue was purified by column chromatography on silica gel (0% to 30% ethyl acetate in hexanes) to give
2,2,6-trimethyl-4H-1,3-dioxin-4-one.

Hazard category code

11-36/37/38-36

Safety instructions

16-26-27-36/37/39-9-33

Dangerous goods transport number

UN 19933/PG 2

WGK Germany

3

Hazard level

3

Packaging category

Ⅱ

Customs code

29329995