Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

405418

Sigma-Aldrich

2,6-Bis(chloromethyl)pyridine

99%

Synonym(s):

α,α′-Dichloro-2,6-lutidine

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C7H7Cl2N
CAS Number:
Molecular Weight:
176.04
Beilstein/REAXYS Number:
116355
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

solid

mp

73-78 °C (lit.)

functional group

chloro

SMILES string

ClCc1cccc(CCl)n1

InChI

1S/C7H7Cl2N/c8-4-6-2-1-3-7(5-9)10-6/h1-3H,4-5H2

InChI key

IWQNFYRJSVJWQA-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

General description

2,6-Bis(chloromethyl)pyridine is a heterocyclic building block for the synthesis of a variety of pyridine derivatives. It coordinates with metal ions through N-atom to form complexes. The conformational flexibility of the bromomethyl arms makes it an ideal choice for the generation of macrocycles. 2,6-bis(chloromethyl)pyridine crystals are monoclinic with space group P21/c. Its synthesis has been reported. The FT-IR and FT-Raman spectra of 2,6-bis(chloromethyl)pyridine (BCMP) have been recorded in the regions 4000-400cm-1 and 3500-100cm-1, respectively.

Application

2,6-Bis(chloromethyl)pyridine may be used in the following studies:
  • Synthesis of a sensitive fluorescent chemosensor for Hg2+, composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine.
  • Preparation of carbene pincer ligands, required for the preparation of palladium pincer carbene complex.
  • Synthesis of 2-(di-tert-butylphosphinomethyl)-6-diethylaminomethyl)pyridine, PNN ligand.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

An efficient synthesis of 2,6-bis(chloromethyl)pyridine and a [5.5](2,6) pyridinophane disulfite.
Rezzonico B and Grignon-Dubois M.
J. Chem. Res. Synop., 4, 142-143 (1994)
Xiangfeng Guo et al.
Journal of the American Chemical Society, 126(8), 2272-2273 (2004-02-26)
A selective and sensitive fluorescent chemosensor for Hg2+, which was composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine, was synthesized through the reaction of 2,6-bis(chloromethyl)pyridine and N-[2-(2-hydroxyethoxy)ethyl]-4-piperazino-1,8-naphthalimide. The chemosensor showed an about 17-fold increase in fluorescence quantum yield
Iron (II) complexes based on electron-rich, bulky PNN-and PNP-type ligands.
Zhang J, et al.
Inorgorganica Chimica Acta, 359(6), 1955-1960 (2006)
Tridentate carbene CCC and CNC pincer palladium (II) complexes: structure, fluxionality, and catalytic activity.
Grundemann S, et al.
Organometallics, 20(25), 5485-5488 (2001)
2, 6-Bis(bromomethyl) pyridine.
Cuzan O, et al.
Acta Crystallographica Section E, Structure Reports Online, 70(1), 4-4 (2014)

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