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

Basic information Safety Supplier Related

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

Product Name:
2,2,6,6-Tetramethyl-3,5-heptanedione
Synonyms:
  • (CH3)3CCOCH2COC(CH3)3
  • 2,2,6,6-Tetramethyl heptanedione
  • 2,2,6,6-tetramethyl-5-heptanedione
  • TMHD
  • DIPIVALOYLMETHANE
  • 2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONE DIPIVALOYLMETHANE
  • 2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONE
  • 2,2,6,6-TETRAMETHYLHEPTANE-3,5-DIONE
CAS:
1118-71-4
MF:
C11H20O2
MW:
184.28
EINECS:
214-268-3
Product Categories:
  • Achiral Oxygen
  • organic compound
  • Environmentally-friendly Oxidation
  • Ligands (Environmentally-friendly Oxidation)
  • Synthetic Organic Chemistry
  • CHIRAL CHEMICALS
Mol File:
1118-71-4.mol
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2,2,6,6-Tetramethyl-3,5-heptanedione Chemical Properties

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
InChIKey
YRAJNWYBUCUFBD-UHFFFAOYSA-N
LogP
2.818 (est)
CAS DataBase Reference
1118-71-4(CAS DataBase Reference)
EPA Substance Registry System
3,5-Heptanedione, 2,2,6,6-tetramethyl- (1118-71-4)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-40-36/37/38
Safety Statements 
24/25-36-26-22
RIDADR 
UN 1993 / PGIII
WGK Germany 
3
TSCA 
T
HS Code 
29141900

MSDS

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2,2,6,6-Tetramethyl-3,5-heptanedione Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Uses

suzuki reaction

Uses

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

Uses

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.
   

2,2,6,6-Tetramethyl-3,5-heptanedione Preparation Products And Raw materials

Preparation Products

Raw materials

2,2,6,6-Tetramethyl-3,5-heptanedioneSupplier

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