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P51400

Sigma-Aldrich

Propiolic acid

95%

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Synonym(s):
Acetylenecarboxylic acid, Propynoic acid
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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Related Categories

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

WGK

WGK 3

Flash Point(F)

136.4 °F

Flash Point(C)

58 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Tetrahedron, 49, 4229-4229 (1993)
The Journal of Organic Chemistry, 57, 709-709 (1992)
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
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
Shili Xu et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(40), 16348-16353 (2012-09-19)
Protein disulfide isomerase (PDI), an endoplasmic reticulum chaperone protein, catalyzes disulfide bond breakage, formation, and rearrangement. The effect of PDI inhibition on ovarian cancer progression is not yet clear, and there is a need for potent, selective, and safe small-molecule
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