P51400
Propiolic acid
95%
Synonym(s):
Acetylenecarboxylic acid, Propynoic acid
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About This Item
Linear Formula:
HC≡CCOOH
CAS Number:
Molecular Weight:
70.05
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-437-8
Beilstein/REAXYS Number:
878176
MDL number:
Assay:
95%
InChI key
UORVCLMRJXCDCP-UHFFFAOYSA-N
InChI
1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)
SMILES string
OC(=O)C#C
assay
95%
impurities
≤6.0% acetic acid
Quality Level
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
Related Categories
Application
Reagent employed in the synthesis of transition metal complexes, haloalkyl propiolates, and halopropenoates.
signalword
Danger
hcodes
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
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The Journal of Organic Chemistry, 57, 709-709 (1992)
Tetrahedron, 49, 4229-4229 (1993)
Journal of Organometallic Chemistry, 456, 271-271 (1993)
Søren Kramer et al.
Organic letters, 11(18), 4208-4211 (2009-08-25)
A highly regioselective hydroamination of unsymmetrical electron-poor and electron-rich alkynes with anilines catalyzed by Au(I) under mild conditions is reported. In addition, applications toward indole syntheses are presented including an example of a one-pot synthesis from a nonfunctionalized aniline.
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
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