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155756

Sigma-Aldrich

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

98%

Synonym(s):

Dipivaloylmethane

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5 G
$51.30
25 G
$195.00
100 G
$272.00

About This Item

Linear Formula:
(CH3)3CCOCH2COC(CH3)3
CAS Number:
1118-71-4
Molecular Weight:
184.28
Beilstein/REAXYS Number:
1447269
EC Number:
214-268-3
MDL number:
MFCD00008848
UNSPSC Code:
12352100
PubChem Substance ID:
24849563
NACRES:
NA.22

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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. [1] [2]

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.[3][4]

Application

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

2,2,6,6-Tetramethyl-3,5-heptanedione used as a ancillary ligand in the synthesis of orange-emitting iridium(III) complex.[7]

Storage Class

10 - Combustible liquids

wgk_germany

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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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)
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)
Solvent extraction of some lanthanides with 2, 2, 6, 6-tetramethyl-3, 5-heptanedione
Sweet TR and Parlett HW
Analytical Chemistry, 40(12), 1885-1888 (1968)
Thermochemistry of 2, 2, 6, 6-tetramethyl-3, 5-heptanedione chelates of lanthanide group elements
Santos Jr, et al.
Polyhedron, 18, 969-977 (1999)
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
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      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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