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155756

Sigma-Aldrich

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
Beilstein:
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 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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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4462
SHBR8578
SHBR5406
SHBS1025
SHBR6216

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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
Tetrahedron, 48, 6909-6909 (1992)
2, 2, 6, 6-Tetramethyl-3, 5-heptanedione
Jurica EA
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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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    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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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      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.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      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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