2,2,6,6-Tetramethyl-3,5-heptanedione

Synonym(s):Dipivaloylmethane

CAS NO.：1118-71-4
Empirical Formula: C11H20O2
Molecular Weight: 184.28
MDL number: MFCD00008848
EINECS: 214-268-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-28 16:48:35

2,2,6,6-Tetramethyl-3,5-heptanedione Structural

What is 2,2,6,6-Tetramethyl-3,5-heptanedione?

Chemical properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

The Uses of 2,2,6,6-Tetramethyl-3,5-heptanedione

2,2,6,6-tetramethyl-3,5-heptanedione was used in the synthesis of α-aryl-β-diketones1 and dicyanamidobenzene-bridge diruthenium complex.

The Uses of 2,2,6,6-Tetramethyl-3,5-heptanedione

suzuki reaction

The Uses of 2,2,6,6-Tetramethyl-3,5-heptanedione

2,2,6,6-Tetramethyl-3,5-heptanedione is a beta diketone with antibacterial activity.

Definition

2,2,6,6-Tetramethyl-3,5-heptanedioneis a stable, anhydrous reagent. It undergoes O-additions and C-additions. In various reactions, it acts as an air-stable ligand for metal catalysts. Furthermore, it serves as a substrate for heterocycles.

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 5428, 1978 DOI: 10.1021/ja00485a030

General Description

Acylation, a replacement to silylation, allows the conversion of compounds that consist of active hydrogens (-OH, -SH and -NH) into esters, thioesters, and amides via the action of a carboxylic acid or derivative. The carbonyl group adjacent to the halogenated carbons is known to improve the electron capture detector (ECD) response. Acylation has several advantages:

It enhances the stability of compounds by protecting unstable groups.
It may confer volatility on substances like carbohydrates or amino acids, that have several polar groups that they are non-volatile and usually decompose on heating.
It facilitates the separations not possible with underivatized compounds.
Compounds are detectable at very low levels with an ECD.

2,2,6,6-Tetramethyl-3,5-heptanedione is a reagent used to form fragmentation-directing derivatives for GC/MS analysis.

Synthesis

Methyl pivalate and formamide could be used as starting materials to synthesize 2,2,6,6-Tetramethyl-3,5-heptanedione.

Properties of 2,2,6,6-Tetramethyl-3,5-heptanedione

Melting point:	>400 °C (decomp)
Boiling point:	72-73 °C/6 mmHg (lit.)
Density	0.883 g/mL at 25 °C (lit.)
refractive index	n20/D 1.459(lit.)
Flash point:	153 °F
storage temp.	Sealed in dry,Room Temperature
solubility	Difficult to mix.
form	Liquid
pka	11.60±0.10(Predicted)
Specific Gravity	0.883
color	Clear colorless to slightly yellow
BRN	1447269
CAS DataBase Reference	1118-71-4(CAS DataBase Reference)
EPA Substance Registry System	3,5-Heptanedione, 2,2,6,6-tetramethyl- (1118-71-4)

Safety information for 2,2,6,6-Tetramethyl-3,5-heptanedione

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H227:Flammable liquids H302:Acute toxicity,oral
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. P501:Dispose of contents/container to..…