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476420

Sigma-Aldrich

Dimethyl allylmalonate

98%

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About This Item

Linear Formula:
H2C=CHCH2CH(CO2CH3)2
CAS Number:
Molecular Weight:
172.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

refractive index

n20/D 1.435 (lit.)

bp

207 °C/771 mmHg (lit.)

density

1.071 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(CC=C)C(=O)OC

InChI

1S/C8H12O4/c1-4-5-6(7(9)11-2)8(10)12-3/h4,6H,1,5H2,2-3H3

InChI key

VZNFVLWVVHHMBG-UHFFFAOYSA-N

Application

Dimethyl allylmalonate may be used in the preparation of:
  • terminal alkyl silane
  • diallyl malonates
  • bromosulfoxide
  • dimethyl-2-allyl-2-{4-methyl-2-[(tetrahydro-2H-pyran-2-yloxy)methyl]deca-2,3-dienoyl}malonate

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

199.4 °F - closed cup

Flash Point(C)

93 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of substituted cyclopentenes from the Baylis-Hillman adducts via ring-closing metathesis reaction.
Lee KY, et al.
Bull. Korean Chem. Soc., 25(8), 1280-1282 (2004)
Tandem cyclization/hydrosilylation of functionalized 1, 6-dienes catalyzed by a cationic palladium complex.
Widenhoefer RA and DeCarli MA.
Journal of the American Chemical Society, 120(15), 3805-3806 (1998)
The study of intramolecular free radical cyclizations of a-sulfonyl and a-sulfinyl radicals.
Yeun-Min T, et al.
Tetrahedron Letters, 31(42), 6047-6050 (1990)
Krause N.
Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, 138-138 (2014)

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