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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

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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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)
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
Priya Ranjan et al.
Planta, 219(4), 694-704 (2004-05-18)
A PCR-based suppression subtractive hybridization (SSH) technique was used to identify differentially expressed genes in developing tissues of control and transgenic aspen (Populus tremuloides Michx.) with down-regulated 4CL1 (4-coumarate:coenzyme A ligase) expression and enhanced growth. A total of 11,308 expressed
Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids.
Feng C and Loh T P
Chemical Communications (Cambridge, England), 46(26), 4779-4781 (2010)
Iwona Morkunas et al.
Journal of plant physiology, 168(5), 424-433 (2010-11-09)
This study investigated the effects of cross-talk interactions of sucrose and infection caused by a pathogenic fungus Fusarium oxysporum f.sp. lupini on the regulation of the phenylpropanoid pathway, i.e. the level of expression of genes encoding enzymes participating in flavonoid
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