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A21002

Sigma-Aldrich

2-Acetylpyridine

≥99%

Synonym(s):

Methyl 2-pyridyl ketone

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About This Item

Empirical Formula (Hill Notation):
C7H7NO
CAS Number:
1122-62-9
Molecular Weight:
121.14
Beilstein:
107759
EC Number:
214-355-6
MDL number:
MFCD00006303
UNSPSC Code:
12352100
PubChem Substance ID:
24890624
NACRES:
NA.22

Assay

≥99%

form

liquid

refractive index

n20/D 1.521 (lit.)

bp

188-189 °C (lit.)

density

1.08 g/mL at 25 °C (lit.)

SMILES string

CC(=O)c1ccccn1

InChI

1S/C7H7NO/c1-6(9)7-4-2-3-5-8-7/h2-5H,1H3

InChI key

AJKVQEKCUACUMD-UHFFFAOYSA-N

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Application

2-Acetylpyridine can be used in the synthesis of:
  • A near-infrared fluorescent probe for monitoring pH changes in living cells.
  • Biologically active ligands for preparing various metal complexes including Co(II), Ni(II), Cu(II) and Zn(II).
  • A water-soluble, time-gated luminescence probe for singlet oxygen detection.
  • 2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

163.4 °F - closed cup

Flash Point(C)

73 °C - closed cup

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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2-Acetylpyridine thiosemicarbazones are potent iron chelators and antiproliferative agents: redox activity, iron complexation and characterization of their antitumor activity.
Richardson D R, et al.
Journal of Medicinal Chemistry, 52(5), 1459-1470 (2009)
A near-infrared neutral pH fluorescent probe for monitoring minor pH changes: imaging in living HepG2 and HL-7702 cells.
Tang B, et al.
Journal of the American Chemical Society, 131(8), 3016-3023 (2009)
A europium (III) complex as an efficient singlet oxygen luminescence probe.
Song B, et al.
Journal of the American Chemical Society, 128(41), 13442-13450 (2006)
Synthesis, characterization and biological studies of Co (II), Ni (II), Cu (II) and Zn (II) complexes with bidentate Schiff bases derived by heterocyclic ketone.
Singh K, et al.
European Journal of Medicinal Chemistry, 41(1), 147-153 (2006)
Joëlle Akl et al.
Dalton transactions (Cambridge, England : 2003), 43(33), 12721-12733 (2014-07-12)
The 4'-(2-fluorenyl)-2,2':6',2''-terpyridine (FT) ligand and its cis(Cl,Cl)- and trans(Cl,Cl)-[Ru(II)(FT)Cl2(NO)](PF6) complexes have been synthesized. Both isomers were separated by HPLC and fully characterized by (1)H and (13)C NMR. The X-ray diffraction crystal structures were solved for FT (Pna21 space group, a
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