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P31205

Sigma-Aldrich

Phenylpropiolic acid

99%

Synonym(s):

Phenylpropynoic acid

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About This Item

Linear Formula:
C6H5C≡CCOOH
CAS Number:
637-44-5
Molecular Weight:
146.14
Beilstein:
742587
EC Number:
211-285-8
MDL number:
MFCD00004361
UNSPSC Code:
12352100
PubChem Substance ID:
24898391
NACRES:
NA.22

Quality Level

100

Assay

99%

form

crystals

mp

135-137 °C (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)C#Cc1ccccc1

InChI

1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)

InChI key

XNERWVPQCYSMLC-UHFFFAOYSA-N

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Application

Phenylpropiolic acid can:
  • React with 2-tert-butoxypyridine in the presence of boron trifluoride·diethyl etherate to form the corresponding tert-butyl ester.
  • Undergo decarboxylative coupling with aryl halides such as p-chloroiodobenzene and 1-chloro-4-iodobenzene.
  • Undergo halodecarboxylation to form 1-haloalkynes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Zieliński et al.
Isotopes in environmental and health studies, 37(3), 239-252 (2002-04-02)
13C kinetic isotope effect (KIE) in the decarboxylation of phenylpropiolic acid (PPA) in tetralin medium (Tn) has been determined at 409-432 K and found to be of magnitude similar to the 13C KIE observed in the decarboxylation of malonic acid
Neil R McIntyre et al.
Journal of enzyme inhibition and medicinal chemistry, 31(4), 551-562 (2015-05-30)
Peptidylglycine α-amidating monooxygenase (PAM) is a bifunctional enzyme that catalyzes the final reaction in the maturation of α-amidated peptide hormones. Peptidylglycine α-hydroxylating monooxygenase (PHM) is the PAM domain responsible for the copper-, ascorbate- and O2-dependent hydroxylation of a glycine-extended peptide.
K N Kim et al.
The Journal of prosthetic dentistry, 67(6), 794-798 (1992-06-01)
The viscosity of monophase addition silicone impression materials was measured as a function of shear rate. The setting of mixed catalyst and base was prevented by addition of a small amount of phenyl propiolic acid. All products showed a 6-
Jill Wood et al.
Bioorganic & medicinal chemistry letters, 16(18), 4965-4968 (2006-06-30)
A series of 4,5-disubstituted cis-pyrrolidinones was investigated as inhibitors of 17beta-HSD II for the treatment of osteoporosis. Biochemical data for several compounds are given. Compound 42 was selected as the lead candidate.
Jan Schwarzbauer et al.
Water research, 39(19), 4735-4748 (2005-11-11)
Detailed gas chromatographic-mass spectrometric analyses applied to eight Rhine river water samples constituted a comprehensive characterization of the low molecular weight organic contamination. Within the group of predominant anthropogenic contaminants, only a few compounds were characterized as frequently detected or
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