405418
2,6-Bis(chloromethyl)pyridine
99%
Synonym(s):
α,α′-Dichloro-2,6-lutidine
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5 G
$168.00
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
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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
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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.[1] Its synthesis has been reported.[2] 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.[3]
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.[4]
- Preparation of carbene pincer ligands, required for the preparation of palladium pincer carbene complex.[5]
- Synthesis of 2-(di-tert-butylphosphinomethyl)-6-diethylaminomethyl)pyridine, PNN ligand.[6]
signalword
Danger
hcodes
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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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)
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)
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
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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