691380

Sigma-Aldrich

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

Lonza quality, ≥93.0% (GC)

Synonym(s):
TMD, Diketene acetone adduct
Empirical Formula (Hill Notation):
C7H10O3
CAS Number:
Molecular Weight:
142.15
Beilstein/REAXYS Number:
2408
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

Lonza quality

assay

≥93.0% (GC)

manufacturer/tradename

Lonza Ltd

impurities

≤0.10% diketene (GC)
≤0.4% dehydracetic acid (GC)
≤0.5% 4-methyl-3-penten-2-one (GC)
≤6.0% acetone (GC)

refractive index

n20/D 1.460 (lit.)

bp

~275 °C (lit.)
65-67 °C/2 mmHg (lit.)

mp

12-13 °C (lit.)

solubility

H2O: insoluble

density

1.07 g/mL at 25 °C (lit.)

storage temp.

2-8°C

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

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Application

2,2,6-Trimethyl-4H-1,3-dioxin-4-one is generally used as a reactant for the synthesis of acetoacetic esters from aliphatic as well as aromatic alcohols. It can also acetoacetylate amines and thiols.

Packaging

25 kg in composite drum
1 kg in glass bottle

Caution

products darkens with time

Pictograms

FlameExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

hazcat

Eye Irrit. 2 - Flam. Liq. 2

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Synthesis and biological evaluation of some new 1, 4-dihydropyridines containing different ester substitute and diethyl carbamoyl group as anti-tubercular agents
Khoshneviszadeh M, et al.
Bioorganic & Medicinal Chemistry, 17(4), 1579-1586 (2009)
Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1, 4-dihydropyridines as calcium channel antagonist
Miri R, et al.
Bioorganic & Medicinal Chemistry, 14(14), 4842-4849 (2006)
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)

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