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81840

Sigma-Aldrich

Dimethyl propargylmalonate

≥95.0% (GC)

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About This Item

Linear Formula:
HC≡CCH2CH(COOCH3)2
CAS Number:
95124-07-5
Molecular Weight:
170.16
Beilstein:
3539408
MDL number:
MFCD00077856
UNSPSC Code:
12352100
PubChem Substance ID:
57652893
NACRES:
NA.22

Assay

≥95.0% (GC)

form

liquid

refractive index

n20/D 1.444

bp

93-95 °C/7 mmHg (lit.)

density

1.119 g/mL at 20 °C (lit.)

SMILES string

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

InChI

1S/C8H10O4/c1-4-5-6(7(9)11-2)8(10)12-3/h1,6H,5H2,2-3H3

InChI key

PWQAXFWWMXTVFT-UHFFFAOYSA-N

Related Categories

Application

Dimethyl propargylmalonate can be used as a reactant to synthesize:
  • Nitro methylenecyclopentanes by [3+2] annulation reaction with various nitroalkenes in the presence of Triton B.
  • Propargylmalonamides intermediates, applicable in the preparation of ″click BOX″ ligands by copper-catalyzed cycloaddition and oxazoline ring formation reaction.
  • Cyclopentene derivatives by reacting with various α, β-unsaturated ketones using a combination of organocatalysts and transition metal catalysts.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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 ?Click BOX? ligands and preliminary results on their application in the asymmetric copper catalyzed Henry reaction of o-methoxybenzaldehyde
Giunta D, et al.
Results in Chemistry, 3, 100122-100122 (2021)
Combination iminium, enamine and copper (I) cascade catalysis: a carboannulation for the synthesis of cyclopentenes
Yang T, et al.
Chemical Communications (Cambridge, England), (25), 2923-2925 (2008)
One-pot Michael addition/intramolecular carbocyclization of dimethyl propargylmalonate with nitroalkenes: A new stereoselective [3+ 2] annulation to 1-nitro 2-methylenecyclopentanes
Guillaume M, et al.
Synlett, 2002(11), 1883-1885 (2002)

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