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Merck
CN

81860

Propiolic acid

technical, ≥95% (T)

Synonym(s):

Acetylenecarboxylic acid, Propynoic acid

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About This Item

Linear Formula:
HC≡CCOOH
CAS Number:
Molecular Weight:
70.05
EC Number:
207-437-8
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
878176
MDL number:
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InChI key

UORVCLMRJXCDCP-UHFFFAOYSA-N

InChI

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

SMILES string

OC(=O)C#C

grade

technical

assay

≥95% (T)

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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

136.4 °F - closed cup

flash_point_c

58 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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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
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)
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
Dingyi Yu et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(47), 20184-20189 (2010-11-10)
The use of carbon dioxide as a renewable and environmentally friendly source of carbon in organic synthesis is a highly attractive approach, but its real world applications remain a great challenge. The major obstacles for commercialization of most current protocols
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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