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738271

Sigma-Aldrich

3-Butynoic acid

95%

Synonym(s):

2-Ethynylacetic acid

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About This Item

Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
2345-51-9
Molecular Weight:
84.07
MDL number:
MFCD02258494
UNSPSC Code:
12352100
NACRES:
NA.22

Quality Level

100

assay

95%

form

powder

mp

70-80 °C

SMILES string

OC(=O)CC#C

InChI

1S/C4H4O2/c1-2-3-4(5)6/h1H,3H2,(H,5,6)

InChI key

KKAHGSQLSTUDAV-UHFFFAOYSA-N

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Application

Some of the applications of 3-butynoic acid are:
  • Synthesis of functionalized γ-butyrolactones and tetrahydrofurans via Conia-ene cyclizations.
  • Synthesis of allenoates for [2+2] cycloadditions with alkenes.
  • Phosphine-catalyzed synthesis of highly functionalized coumarins.
  • Synthesis of various useful organotin reagents via radical hydrostannation of 3-butynoic acid.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT6659
MKCS5343
MKCQ8433
MKCP1130
MKCM0872

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Synergistic Diazo?OH Insertion/Conia?Ene Cascade Catalysis for the Stereoselective Synthesis of ??Butyrolactones and Tetrahydrofurans.
Hunter A C, et al.
Chemistry?A European Journal , 22(45), 16062-16065 (2016)
Catalytic Enantioselective Allenoate?Alkene [2+ 2] Cycloadditions.
Conner M L, et al.
Journal of the American Chemical Society, 137(10), 3482-3485 (2015)
Phosphine-catalyzed synthesis of highly functionalized coumarins.
Henry C E and Kwon O
Organic Letters, 9(16), 3069-3072 (2007)
Zhipeng Li et al.
The Analyst, 145(12), 4239-4244 (2020-05-22)
The aim of this study was to overcome the reported shortcomings of the glutathione (GSH) detection of rhodamine-based fluorescent probes, such as poor selectivity to thiol groups and reversible unstable covalent binding with the thiol groups. Here, we have developed
Ionogels, new materials arising from the confinement of ionic liquids within silica-derived networks.
Neouze M A, et al.
Chemistry of Materials, 18(17), 3931-3936 (2006)

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