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P51400

Sigma-Aldrich

Propiolic acid

95%

Synonym(s):

Acetylenecarboxylic acid, Propynoic acid

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About This Item

Linear Formula:
HC≡CCOOH
CAS Number:
471-25-0
Molecular Weight:
70.05
Beilstein:
878176
EC Number:
207-437-8
MDL number:
MFCD00004360
UNSPSC Code:
12352100
PubChem Substance ID:
24898598
NACRES:
NA.22

Quality Level

200

Assay

95%

impurities

≤6.0% acetic acid

refractive index

n20/D 1.431 (lit.)

bp

102 °C/200 mmHg (lit.)

mp

16-18 °C (lit.)

density

1.138 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)C#C

InChI

1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)

InChI key

UORVCLMRJXCDCP-UHFFFAOYSA-N

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Application

Reagent employed in the synthesis of transition metal complexes, haloalkyl propiolates, and halopropenoates.

Signal Word

Danger

Hazard Statements

H226,H301,H310,H314

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

136.4 °F - closed cup

Flash Point(C)

58 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL0584
STBK7647
STBK1697
0000111256
STBJ9377

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Tetrahedron, 49, 4229-4229 (1993)
The Journal of Organic Chemistry, 57, 709-709 (1992)
Wonyoung Kim et al.
Organic letters, 15(7), 1654-1657 (2013-03-15)
Diarylalkynones were synthesized from one-pot Pd-catalyzed carbonylative and noncarbonylative coupling reactions of propiolic acid with aryl iodides under a carbon monoxide atmosphere. Aryl iodide (2.0 equiv), propiolic acid (1.0 equiv), Pd(PPh3)2Cl2 (5 mol %), CuCl (10 mol %), Et3N (6.0
Jihye Park et al.
The Journal of organic chemistry, 76(7), 2214-2219 (2011-03-05)
One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocoupling is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cross-coupling of two different
Tina N Grant et al.
Organic letters, 10(18), 3985-3988 (2008-08-19)
Readily available five- and six-membered lactones and N-sulfonyllactams undergo efficient addition of t-butyl propiolate, and the resulting adducts undergo cycloisomerization to six- and seven-membered cyclic ethers or amines in the presence of pyridinium acetate. The ring expansion process occurs in
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