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Merck
CN

81860

Sigma-Aldrich

Propiolic acid

technical, ≥95% (T)

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:
329769222

Key Documents

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grade

technical

Assay

≥95% (T)

refractive index

n20/D 1.431 (lit.)
n20/D 1.431

bp

102 °C/200 mmHg (lit.)

mp

16-18 °C (lit.)

density

1.135 g/mL at 20 °C
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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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

Regulatory Information

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Regiodivergent ligand-controlled rhodium-catalyzed [(2+2)+2] carbocyclization reactions with alkyl substituted methyl propiolates.
P Andrew Evans et al.
Angewandte Chemie (International ed. in English), 49(33), 5746-5749 (2010-07-16)
Sándor Kun et al.
Carbohydrate research, 346(12), 1427-1438 (2011-04-08)
5-(O-Perbenzoylated-β-D-glucopyranosyl)tetrazole was obtained from O-perbenzoylated-β-D-glucopyranosyl cyanide by Bu(3)SnN(3) or Me(3)SiN(3)-Bu(2)SnO. This tetrazole was transformed into 5-ethynyl- as well as 5-chloromethyl-2-(O-perbenzoylated-β-D-glucopyranosyl)-1,3,4-oxadiazoles by acylation with propiolic acid-DCC or chloroacetyl chloride, respectively. The chloromethyl oxadiazole gave the corresponding azidomethyl derivative on treatment with
Huangdi Feng et al.
The Journal of organic chemistry, 77(11), 5149-5154 (2012-05-09)
A novel microwave-assisted approach for the one-pot Cu(I)-catalyzed A(3)-coupling/decarboxylative coupling (PA(2)-coupling) of a propiolic acid, an aldehyde, and an amine, resulting in the formation of diversely substituted 1,4-diamino-2-butynes,is described. It is noteworthy that this new multicomponent coupling provides an efficient
Terence C Owen
Bioorganic chemistry, 36(3), 156-160 (2008-04-02)
Thiols, simple and complex, including polypeptide and protein thiols, react rapidly and selectively with esters of propiolic acid under very mild conditions (aqueous buffer, room temperature, pH 7) to give thioacrylates. These stable derivatives exhibit strong, characteristic ultraviolet spectra, maximal
Hyun-Suk Yeom et al.
Journal of the American Chemical Society, 134(1), 208-211 (2011-12-01)
A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to α,β-unsaturated
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