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Merck
CN

299383

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

technical grade

Synonym(s):

Diketene acetone adduct

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About This Item

Empirical Formula (Hill Notation):
C7H10O3
CAS Number:
5394-63-8
Molecular Weight:
142.15
EC Number:
226-403-3
UNSPSC Code:
12352100
PubChem Substance ID:
24858039
Beilstein/REAXYS Number:
2408
MDL number:
MFCD00040468

Key Documents

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InChI key

XFRBXZCBOYNMJP-UHFFFAOYSA-N

InChI

1S/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3

SMILES string

CC1=CC(=O)OC(C)(C)O1

grade

technical grade

bp

~275 °C (lit.), 65-67 °C/2 mmHg (lit.)

mp

12-13 °C (lit.)

solubility

water: insoluble

density

1.07 g/mL at 25 °C (lit.)

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General description

Flash pyrolysis of 2,2,6-trimethyl-4H-1,3-dioxin-4-one generates acetylketene. It is a diketene-acetone adduct.

Application

2,2,6-trimethyl-4H-1,3-dioxin-4-one was used for acetoacetylation of aliphatic and aromatic alcohols, amines and thiols. It was also used in preparation of N-alkenyl acetoacetamides.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

57.2 °F - closed cup

flash_point_c

14 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
06920ME
08327CE
S33910
06321PD
18211BS

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Reaction of 2, 2, 6-trimethyl-4H-1, 3-dioxin-4-one with imines: an easy route to enamides.
D'Annibale A, et al.
Tetrahedron Letters, 37(41), 7429-7432 (1996)
Acetoacetylation with 2, 2, 6-trimethyl-4H-1, 3-dioxin-4-one: a convenient alternative to diketene.
Clemens RJ and Hyatt JA.
The Journal of Organic Chemistry, 50(14), 2431-2435 (1985)
David M. Birney et al.
The Journal of organic chemistry, 62(21), 7114-7120 (2001-10-24)
Acetylketene (1) was generated by flash pyrolysis of 2,2,6-trimethyl-4H-1,3-dioxin-4-one (6). The selectivities of 1 toward a number of representative functional groups were measured for the first time in a series of competitive trapping reactions. The trend in reactivities toward 1

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