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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

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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Rocío Gómez-Vásquez et al.
Annals of botany, 94(1), 87-97 (2004-05-18)
Control of diseases in the key tropical staple, cassava, is dependent on resistant genotypes, but the innate mechanisms are unknown. The aim was to study phenylpropanoids and associated enzymes as possible defence components. Phenylalanine ammonia-lyase (PAL), phenylpropanoids and peroxidases (POD)
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.
Elizabeth Joubert et al.
Food chemistry, 136(2), 1078-1085 (2012-11-06)
Z-2-(β-d-glucopyranosyloxy)-3-phenylpropenoic acid (PPAG), a compound postulated to contribute to the taste and mouthfeel of fermented rooibos tea (Aspalathus linearis), was isolated from unfermented rooibos plant material. Its structure was unequivocally confirmed by LC-MS, -MS(2), FT-IR and NMR of the underivatised
A fast and practical synthesis of tert-butyl esters from 2-tert-butoxypyridine using boron trifluoride? diethyl etherate under mild conditions.
La M T and Kim H K
Tetrahedron, 74(27), 3748-3754 (2018)
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