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405418

Sigma-Aldrich

2,6-Bis(chloromethyl)pyridine

99%

Synonym(s):

α,α′-Dichloro-2,6-lutidine

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About This Item

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

Quality Level

Assay

99%

form

solid

mp

73-78 °C (lit.)

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

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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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

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

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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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)
Tridentate carbene CCC and CNC pincer palladium (II) complexes: structure, fluxionality, and catalytic activity.
Grundemann S, et al.
Organometallics, 20(25), 5485-5488 (2001)
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)
2, 6-Bis(bromomethyl) pyridine.
Cuzan O, et al.
Acta Crystallographica Section E, Structure Reports Online, 70(1), 4-4 (2014)

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