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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
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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.[1]
  • Synthesis of allenoates for [2+2] cycloadditions with alkenes.[2]
  • Phosphine-catalyzed synthesis of highly functionalized coumarins.[3]
  • Synthesis of various useful organotin reagents via radical hydrostannation of 3-butynoic acid.[4]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301 + H311,H314

Hazard Classifications

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

Storage Class Code

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

WGK

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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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
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)
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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