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405418

Sigma-Aldrich

2,6-Bis(chloromethyl)pyridine

99%

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Synonym(s):
α,α′-Dichloro-2,6-lutidine
Empirical Formula (Hill Notation):
C7H7Cl2N
CAS Number:
Molecular Weight:
176.04
Beilstein/REAXYS Number:
116355
MDL number:
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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1 of 4

This Item
27097033553379433
vibrant-m

405418

2,6-Bis(chloromethyl)pyridine

-
vibrant-m

270970

Pyridine

-
vibrant-m

33553

Pyridine

Essential Grade
vibrant-m

379433

2,6-Bis(2-benzimidazolyl)pyridine

-
Quality Level

100

Quality Level

200, 300

Quality Level

200

Quality Level

100

mp

73-78 °C (lit.)

mp

−42 °C (lit.)

mp

−42 °C (lit.)

mp

>300 °C (lit.)

form

solid

form

liquid

form

liquid

form

-

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


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Customers Also Viewed

Slide 1 of 4

1 of 4

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
Tridentate carbene CCC and CNC pincer palladium (II) complexes: structure, fluxionality, and catalytic activity.
Grundemann S, et al.
Organometallics, 20(25), 5485-5488 (2001)
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)
V Balachandran et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 97, 1023-1032 (2012-08-29)
The FT-IR and FT-Raman spectra of 2,6-Bis(chloromethyl)pyridine (BCMP) have been recorded in the regions 4000-400 cm(-1) and 3500-100 cm(-1), respectively. The total energy calculations of BCMP were tried for the possible rotational isomers. The molecular structure, geometry optimization, vibrational frequencies
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)

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