155756
2,2,6,6-Tetramethyl-3,5-heptanedione
98%
Synonym(s):
Dipivaloylmethane
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About This Item
Linear Formula:
(CH3)3CCOCH2COC(CH3)3
CAS Number:
Molecular Weight:
184.28
Beilstein:
1447269
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
98%
form
liquid
refractive index
n20/D 1.459 (lit.)
bp
72-73 °C/6 mmHg (lit.)
density
0.883 g/mL at 25 °C (lit.)
functional group
ketone
SMILES string
CC(C)(C)C(=O)CC(=O)C(C)(C)C
InChI
1S/C11H20O2/c1-10(2,3)8(12)7-9(13)11(4,5)6/h7H2,1-6H3
InChI key
YRAJNWYBUCUFBD-UHFFFAOYSA-N
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General description
2,2,6,6-Tetramethyl-3,5-heptanedione is a bidentate ligand used in the synthesis of stable complexes with lanthanide ions.
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.
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.
Application
2,2,6,6-tetramethyl-3,5-heptanedione was used in the synthesis of α-aryl-β-diketones and dicyanamidobenzene-bridge diruthenium complex.
2,2,6,6-Tetramethyl-3,5-heptanedione used as a ancillary ligand in the synthesis of orange-emitting iridium(III) complex.
2,2,6,6-Tetramethyl-3,5-heptanedione used as a ancillary ligand in the synthesis of orange-emitting iridium(III) complex.
Storage Class Code
10 - Combustible liquids
WGK
WGK 1
Flash Point(F)
152.6 °F - closed cup
Flash Point(C)
67 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Synthesis and characterization of phenylpyridine derivative containing an imide functional group on an iridium (III) complex for solution-processable orange-phosphorescent organic light-emitting diodes
Hwang J, et al.
Dyes and Pigments, 121, 73-78 (2015)
Muriel Fabre et al.
Inorganic chemistry, 45(23), 9332-9345 (2006-11-07)
The dicyanamidobenzene-bridge diruthenium complex [{Ru(tpy)(thd)}(2)(mu-dicyd)][PF(6)] ([3][PF(6)]) (dicyd = 1,4-dicyanamidobenzene, tpy = 2,2':6',2' '-terpyridine, thd = 2,2,6,6-tetramethyl-3,5-heptanedione) and its mononuclear counterpart [Ru(tpy)(thd)(Ipcyd)] (2) [Ipcyd = 4-iodophenylcyanamide anion (Ipcyd(-))] were synthesized and fully characterized. Cyclic voltammetry of 3 showed the presence of
2, 2, 6, 6-Tetramethyl-3, 5-heptanedione
Jurica EA
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Elizabeth Buck et al.
Organic letters, 4(9), 1623-1626 (2002-04-27)
[reaction: see text]. In the copper salt catalyzed ether formation from aryl bromides or iodides and phenols, 2,2,6,6-tetramethylheptane-3,5-dione (TMHD) was found to greatly accelerate the ordinarily difficult reaction, making it occur under more moderate temperatures and reaction times. A series
Franklin P Ow et al.
The journal of physical chemistry. A, 110(25), 7751-7754 (2006-06-23)
Laser photoionization and ligand photodissociation in Ln(thd)(3) (Ln = Eu, Tb, Gd; thd = 2,2,6,6-tetramethyl-3,5-heptanedionato) are studied in a molecular beam via time-of-flight mass spectrometry. The fragmentation patterns are strongly wavelength dependent. With 355 nm excitation, the mass spectrum is
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