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49362

Sigma-Aldrich

Dimethyl glutaconate

≥95.0% (GC)

Synonym(s):

Dimethyl 2-pentenoate

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About This Item

Linear Formula:
CH3OOCCH2CH=CHCOOCH3
CAS Number:
5164-76-1
Molecular Weight:
158.15
Beilstein/REAXYS Number:
1724169
MDL number:
MFCD00066240
UNSPSC Code:
12352100
PubChem Substance ID:
57651186
NACRES:
NA.22

assay

≥95.0% (GC)

refractive index

n20/D 1.452

density

1.124 g/mL at 20 °C (lit.)

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+

InChI key

SKCGFFOFYXLNCG-ONEGZZNKSA-N

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

Components

composition: ~83% trans + ~17% cis

hcodes

H412

Hazard Classifications

Aquatic Chronic 3

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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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)
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)
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)
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)

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