81840
Dimethyl propargylmalonate
≥95.0% (GC)
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About This Item
Linear Formula:
HC≡CCH2CH(COOCH3)2
CAS Number:
Molecular Weight:
170.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3539408
Assay:
≥95.0% (GC)
Form:
liquid
InChI
1S/C8H10O4/c1-4-5-6(7(9)11-2)8(10)12-3/h1,6H,5H2,2-3H3
SMILES string
COC(=O)C(CC#C)C(=O)OC
InChI key
PWQAXFWWMXTVFT-UHFFFAOYSA-N
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.)
functional group
ester
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves
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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)
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)
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