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713309

Sigma-Aldrich

Methyl 2-oxobutanoate

95%

Synonym(s):

2-Oxobutyric acid methyl ester, Methyl 2-ketobutyrate

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About This Item

Empirical Formula (Hill Notation):
C5H8O3
CAS Number:
3952-66-7
Molecular Weight:
116.12
Beilstein/REAXYS Number:
1749847
MDL number:
MFCD03093092
UNSPSC Code:
12352100
PubChem Substance ID:
329763189
NACRES:
NA.22

Quality Level

100

assay

≥95.0% (GC)
95%

form

liquid

impurities

≤1.0% water

SMILES string

CCC(=O)C(=O)OC

InChI

1S/C5H8O3/c1-3-4(6)5(7)8-2/h3H2,1-2H3

InChI key

XPIWVCAMONZQCP-UHFFFAOYSA-N

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Application

Methyl 2-oxobutanoate can be used as a starting material:
  • To synthesize indole derivatives via Fischer indolization of arylhydrazines using propylphosphonic anhydride.
  • In the synthesis of (−)-picrotoxinin, a natural product and neurotoxic sesquiterpenoid.
  • To prepare the core structure of phalarine, a natural product found in perennial grass.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

122.0 °F

flash_point_c

50 °C

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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Synthesis of the core structure of phalarine
Douki K, et al.
Organic & Biomolecular Chemistry, 17, 1727-1730 (2019)
A microwave-assisted, propylphosphonic anhydride (T3P) mediated one-pot Fischer indole synthesis
Desroses M, et al.
Tetrahedron Letters, 52, 4417-4420 (2011)
Synthesis of (−)-Picrotoxinin by Late-Stage Strong Bond Activation
Crossley SWM, et al.
Journal of the American Chemical Society, 142, 11376-11381 (2020)

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