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:
Molecular Weight:
142.15
EC Number:
226-403-3
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
2408
MDL number:
grade
technical grade
refractive index
n20/D 1.460 (lit.)
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.)
SMILES string
CC1=CC(=O)OC(C)(C)O1
InChI
1S/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3
InChI key
XFRBXZCBOYNMJP-UHFFFAOYSA-N
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.
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signalword
Danger
hcodes
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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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