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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
2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONE Structure
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.)
Fp 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)
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 Information
Provider Language
SigmaAldrich English
ACROS English
ALFA English
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.
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.
2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONE Preparation Products And Raw materials
Raw materials Ethanol-->Hydrochloric acid-->Ethyl acetate-->Diethyl ether-->Tetrahydrofuran-->N,N-Dimethylformamide-->Sodium hydride-->Pinacolone-->Methyl trimethylacetate-->4-Heptyn-3-one, 2,2,6,6-tetramethyl--->Benzenemethanamine, N-(1,2,2-trimethylpropylidene)--->Dipivaloylamine-->2,2-Dimethylpropanoic acid phenyl ester-->Propanamide,2,2-dimethyl-N-(phenylmethyl)--->2,3,3-TRIMETHYL-2-BUTANOL-->8-Hydroxyquinoline
Preparation Products N,N-DIPHENYLQUINACRIDONE-->2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO POTASSIUM-->3,5-Heptanedione, 4-bromo-2,2,6,6-tetramethyl-