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Key Documents

510246

Sigma-Aldrich

Methyl 3,3,3-trifluoropyruvate

97%

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About This Item

Linear Formula:
CF3COCO2CH3
CAS Number:
Molecular Weight:
156.06
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.332 (lit.)

bp

86 °C (lit.)

density

1.529 g/mL at 25 °C (lit.)

SMILES string

COC(=O)C(=O)C(F)(F)F

InChI

1S/C4H3F3O3/c1-10-3(9)2(8)4(5,6)7/h1H3

InChI key

XGLLQDIWQRQROJ-UHFFFAOYSA-N

General description

Methyl 3,3,3-trifluoropyruvate is an alkyl 3,3,3-trifluoropyruvate that can be synthesized using hexafluoropropene-1,2-oxide (HFPO) as a starting material. It reacts with aromatic amines, benzylic manoamines and diamines to form the corresponding hemiaminals.

Application

Methyl 3,3,3-trifluoropyruvate may be used in the synthesis of:
  • 2-hydroxy-2-trifluoromethylbutan-4-olides
  • 2-(trifluoromethyl)butan-4-olides
  • 4-trifluoromethyl-(2H)-pyridazin-3-ones
  • methyl 3-methoxy-2-trifluoromethylacrylate

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °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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Fluorinated butanolides and butenolides: Part 8. 2-(Trifluoromethyl) butan-4-olides by synthesis from methyl 3, 3, 3-trifluoropyruvate as building block.
Paleta O, et al.
Journal of Fluorine Chemistry, 111(2), 175-184 (2001)
Fluorine-Sacrificial Cyclizations as an Access to 5-Fluoropyrazoles.
Volle JN and Schlosser M.
European Journal of Organic Chemistry, 2000(5), 823-828 (2000)
Methyl 3, 3, 3-trifluoropyruvate hemiaminals: Stability and transaminations.
Dolensky B, et al.
Journal of Fluorine Chemistry, 126(5), 745-751 (2005)
A convenient synthesis of 4-trifluoromethyl-(2H)-pyridazin-3-ones from methyl 3, 3, 3-trifluoropyruvate.
Sibgatulin DA, et al.
Synlett, 12, 1907-1911 (2005)
Methyl 3,3,3-trifluoropyruvate: an improved procedure starting from hexafluoropropene-1, 2-oxide; identification of byproducts.
Dolensky B, et al.
Journal of Fluorine Chemistry, 115(1), 67- 74 (2002)

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