Skip to Content
Merck

392189

Sigma-Aldrich

1-Pyreneacetic acid

97%

Synonym(s):

(1-Pyrenyl)acetic acid

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C18H12O2
CAS Number:
Molecular Weight:
260.29
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

Quality Level

Assay

97%

form

solid

mp

210-212 °C (dec.) (lit.)

SMILES string

OC(=O)Cc1ccc2ccc3cccc4ccc1c2c34

InChI

1S/C18H12O2/c19-16(20)10-14-7-6-13-5-4-11-2-1-3-12-8-9-15(14)18(13)17(11)12/h1-9H,10H2,(H,19,20)

InChI key

SDJCLYBBPUHKCD-UHFFFAOYSA-N

General description

1-Pyreneacetic acid is a negatively charged pyrene derivative.[1] It has been proposed as titrating reagent for the standardization titration of Grignard reagents[2] and n-butyl lithium (n-BuLi).[3]

Application

1-Pyreneacetic acid is suitable for use in the following studies:
  • Synthesis of N-(2-(methylthio)ethyl)-2-(pyren-1-yl)acetamide, a pyrene amide based Pd2+ probe.[4]
  • Synthesis of pyrene-modified β-cyclodextrin.[5]
  • To functionalize single walled carbon nanotube field effect transistors (CNT FETs).[6]
  • As an agent for characterizing grafting degrees and reactivity of the ester functionalized polypropylenes.[7]
  • Synthesis sawhorse-type diruthenium tetracarbonyl complexes.[8]
  • Synthesis of (±)-2-(1-pyrenyl)propionic acid, a chiral carboxylic acid.[9]
  • Reversible noncovalent functionalization of single walled carbon nanotubes (SWNTs).[10]
  • Preparation of peptide nucleic acid (PNA) probes.[11]
  • As an internal reference compound in the assessment of solid phase reaction by HPLC-UV.[12]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Jan Spengler et al.
ACS combinatorial science, 15(5), 229-234 (2013-03-26)
Here we evaluated the use of internal reference compounds for the rapid assessment of reactions performed in solid-phase. An internal reference compound (commercially available) was bound to the resin, together with the substrate, and cleaved with the products after completion
Sawhorse-type diruthenium tetracarbonyl complexes derived from pyrenyl-carboxylic acids.
Johnpeter JP and Therrien B.
Inorgorganica Chimica Acta, 405, 437-443 (2013)
Gabriela Ramos Chagas et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 18(23), 3429-3436 (2017-09-01)
A smart stimuli-responsive surface was fabricated by the electro-copolymerization of pyrene monomers followed by base and acid treatment. Copolymers of pyrenes bearing fluorinated chains (Py-nF
Alex Manicardi et al.
Beilstein journal of organic chemistry, 10, 1495-1503 (2014-08-28)
Pyrene derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, peptide nucleic acids (PNAs) containing 1 to 3 1-pyreneacetic acid units (PNA1-6) with a sequence with prevalence of pyrimidine
Murphy PJ.
Organophosphorus Reagents: A Practical Approach in Chemistry, 8-8 (2004)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service