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Merck
CN

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:
1118-71-4
Molecular Weight:
184.28
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24849563
EC Number:
214-268-3
Beilstein/REAXYS Number:
1447269
MDL number:
MFCD00008848
Assay:
98%
Form:
liquid

Key Documents

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InChI key

YRAJNWYBUCUFBD-UHFFFAOYSA-N

InChI

1S/C11H20O2/c1-10(2,3)8(12)7-9(13)11(4,5)6/h7H2,1-6H3

SMILES string

CC(C)(C)C(=O)CC(=O)C(C)(C)C

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

Quality Level

200

Related Categories

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.

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.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4462
SHBR8578
SHBR5406
SHBS1025
SHBR6216

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2, 2, 6, 6-Tetramethyl-3, 5-heptanedione
Jurica EA
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Tetrahedron, 48, 6909-6909 (1992)
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
Structure, intramolecular hydrogen bonding, and vibrational spectra of 2, 2, 6, 6-tetramethyl-3, 5-heptanedione
Vakili, Mohamad and Tayyari, et al.
Journal of Molecular Structure, 970, 160-170 (2010)
Thermochemistry of 2, 2, 6, 6-tetramethyl-3, 5-heptanedione chelates of lanthanide group elements
Santos Jr, et al.
Polyhedron, 18, 969-977 (1999)
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