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Sigma-Aldrich

Ethyl 4,4,4-trifluoro-2-butynoate

97%

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About This Item

Linear Formula:
CF3C≡CCO2C2H5
CAS Number:
79424-03-6
Molecular Weight:
166.10
Beilstein/REAXYS Number:
3539414
MDL number:
MFCD00192167
UNSPSC Code:
12352100
PubChem Substance ID:
24865017
NACRES:
NA.22

Quality Level

100

assay

97%

form

liquid

refractive index

n20/D 1.350 (lit.)

bp

96-98 °C (lit.)

density

1.162 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C#CC(F)(F)F

InChI

1S/C6H5F3O2/c1-2-11-5(10)3-4-6(7,8)9/h2H2,1H3

InChI key

SFDRHPQGYUYYNX-UHFFFAOYSA-N

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General description

Ethyl 4,4,4-trifluoro-2-butynoate is an unsymmetrical internal alkyne.

Application

Ethyl 4,4,4-trifluoro-2-butynoate has been used to investigate the regioselectivity of the insertion reaction with cyclometalated iridium and rhodium complexes.

It may be used in the synthesis of the following compounds :
  • (2S,4aR,6aR,7R,9S,10aS,10bR)-methyl 9-acetoxy-2-(5-(ethoxycarbonyl)-6-(trifluoromethyl)-7-oxabicyclo[2.2.1]hepta-2,5-dien-2-yl)-6a,10b-dimethyl-4,10-dioxododecahydro-1H-benzo[f]isochromene-7-carboxylate
  • (2S,4aR,6aR,7R,9S,10aS,10bR)-methyl 9-acetoxy-2-(6-(ethoxycarbonyl)-5-(trifluoromethyl)-7-oxabicyclo[2.2.1]hepta-2,5-dien-2-yl)-6a,10b-dimethyl-4,10-dioxododecahydro-1Hbenzo[f]isochromene-7-carboxylate

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, 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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Reactivity and Regioselectivity of Insertion of Unsaturated Molecules into M- C (M= Ir, Rh) Bonds of Cyclometalated Complexes.
Li L, et al.
Organometallics, 29(20), 4593-4605 (2010)
Anthony Lozama et al.
Journal of natural products, 74(4), 718-726 (2011-02-23)
As part of our continuing efforts toward more fully understanding the structure-activity relationships of the neoclerodane diterpene salvinorin A, we report the synthesis and biological characterization of unique cycloadducts through [4+2] Diels-Alder cycloaddition. Microwave-assisted methods were developed and successfully employed
Facile access to stereodefined dienoates and cyclopropylenoates containing a trifluoromethyl group.
Wang P-A, et al.
Journal of Fluorine Chemistry, 124(1), 93-97 (2003)

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