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235032

Sigma-Aldrich

Bis(trimethylsilyl) malonate

98%

Synonym(s):

Malonic acid bis(trimethylsilyl ester)

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About This Item

Linear Formula:
(CH3)3SiOCOCH2COOSi(CH3)3
CAS Number:
18457-04-0
Molecular Weight:
248.42
Beilstein:
2212115
EC Number:
242-342-5
MDL number:
MFCD00009631
UNSPSC Code:
12352100
PubChem Substance ID:
24854074
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.416 (lit.)

bp

63-66 °C/1 mmHg (lit.)

density

0.974 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)OC(=O)CC(=O)O[Si](C)(C)C

InChI

1S/C9H20O4Si2/c1-14(2,3)12-8(10)7-9(11)13-15(4,5)6/h7H2,1-6H3

InChI key

ATCKJLDGNXGLAO-UHFFFAOYSA-N

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General description

Bis(trimethylsilyl) malonate is precursor for metal-organic chemical vapor deposition (MOCVD) of HfO2 and ZrO2 thin films. It undergoes acylation reaction with acid chlorides and acyl carbonates in the presence of triethylamine and magnesium or lithium salts to give β-keto acids or methyl ketones.

Application

Bis(trimethylsilyl) malonate was used as cyclocondensation agent in cyclocondensation reactions. It was also used in the preparation of β-keto acids and methyl ketones.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

75.2 °F - closed cup

Flash Point(C)

24 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Malonates in cyclocondensation reactions.
Stadlbauer W, et al.
Molecules (Basel), 6(4), 338-352 (2001)
Synthesis of ?-Keto Acids and Methyl Ketones Using Bis (trimethylsilyl) Malonate and Triethylamine in the Presence of Lithium or Magnesium Halides.
Rathke MW and Nowak MA.
Synthetic Communications, 15(12), 1039-1049 (1985)
Synthetic Communications, 15, 1039-1039 (1985)
Ramasamy Pothiraja et al.
Dalton transactions (Cambridge, England : 2003), (4)(4), 654-663 (2009-04-22)
New Hf and Zr malonate complexes have been synthesized by the reaction of metal amides with different malonate ligands (L = dimethyl malonate (Hdmml), diethyl malonate (Hdeml), di-tert-butyl malonate (Hdbml) and bis(trimethylsilyl) malonate (Hbsml)). Homoleptic eight-coordinated monomeric compounds of the

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