49362
Dimethyl glutaconate
≥95.0% (GC)
Synonym(s):
Dimethyl 2-pentenoate
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About This Item
Linear Formula:
CH3OOCCH2CH=CHCOOCH3
CAS Number:
Molecular Weight:
158.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1724169
Assay:
≥95.0% (GC)
InChI key
SKCGFFOFYXLNCG-ONEGZZNKSA-N
SMILES string
COC(=O)C\C=C\C(=O)OC
InChI
1S/C7H10O4/c1-10-6(8)4-3-5-7(9)11-2/h3-4H,5H2,1-2H3/b4-3+
assay
≥95.0% (GC)
refractive index
n20/D 1.452
density
1.124 g/mL at 20 °C (lit.)
functional group
ester
General description
Dimethyl glutaconate, also known as dimethyl 2-pentenoate, is a diester. It reacts with salicaldehyde in the presence of piperidine to form a coumarin-fused electron deficient diene.
Application
Dimethyl glutaconate may be used in the synthesis of:
- dimethyl 3-[(Z)-1-propenyl]glutarate
- phenanthridinone derivatives
- substituted benzenes
Other Notes
composition: ~83% trans + ~17% cis
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 3
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Electron Deficient Dienes. 2. One Step Synthesis of a Coumarin-Fused Electron Deficient Diene and its Inverse Electron Demand Diels-Alder Reactions with Enamines.
Bodwell GJ, et al.
Synlett, 4, 477-479 (1999)
One-Pot Synthesis of Phenanthridinones by Using a Base-Catalyzed/Promoted Bicyclization of a, ?-Unsaturated Carbonyl Compounds with Dimethyl Glutaconate.
Li L, et al.
European Journal of Organic Chemistry, 2015(22), 4892- 4899 (2015)
A convenient method for the preparation of 3-substituted glutarate diesters.
Leotta III, et al.
The Journal of Organic Chemistry, 59(7), 1946-1946 (1994)
Base-Catalyzed Efficient Tandem [3+3] and [3+2+1] Annulation-Aerobic Oxidative Benzannulations.
Diallo A, et al.
Organic Letters, 14(22), 5776-5779 (2012)
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