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405426

Sigma-Aldrich

2,6-Bis(bromomethyl)pyridine

98%

Synonym(s):

α,α′-Dibromo-2,6-lutidine, 1,6-Bis(bromomethyl)pyridine, 2,6-Di(bromomethyl)pyridine

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About This Item

Empirical Formula (Hill Notation):
C7H7Br2N
CAS Number:
7703-74-4
Molecular Weight:
264.95
MDL number:
MFCD00191795
UNSPSC Code:
12352100
PubChem Substance ID:
24865316
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

85-87 °C (lit.)

SMILES string

BrCc1cccc(CBr)n1

InChI

1S/C7H7Br2N/c8-4-6-2-1-3-7(5-9)10-6/h1-3H,4-5H2

InChI key

QUTSYCOAZVHGGT-UHFFFAOYSA-N

Related Categories

General description

Crystal of 2,6-bis(bromomethyl)pyridine has the molecules related by a c-glide-plane operation. Molecules are arranged into stacks along the c axis. It participates in the synthesis of dicationic imidazolium-linked cyclophane.

Application

2,6-Bis(bromomethyl)pyridine may be used in the preparation of the following:
  • a new pyridine-pyrazole derivative, 2,6-bis(3,5-diphenylpyrazol-1-ylmethyl)pyridine
  • a large macrocyclic ligand, N(1),N(7)-pyridine-2,6-dimethyl-N(2),N(6)-bis(6-(3-(1H-benzo[d]imidazol-1-yl)propanamido)pyridin-2-yl)pyridine-2,6-dicarboxamide dibromide
  • small-ring, potentially tridentate Se(2)N(pyridyl)-donor macrocycles

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Kim Meyer et al.
Dalton transactions (Cambridge, England : 2003), 41(46), 14059-14067 (2012-09-11)
Treatment of N(2),N(6)-bis(6-acrylamidopyridin-2-yl)pyridine-2,6-dicarboxamide with benzimidazole gives the acyclic aza-Michael addition product N(2),N(6)-bis(6-(3-(1H-benzo[d]imidazol-1-yl)propanamido)pyridin-2-yl)pyridine-2,6-dicarboxamide (2). The macrocycle N(1),N(7)-pyridine-2,6-dimethyl-N(2),N(6)-bis(6-(3-(1H-benzo[d]imidazol-1-yl)propanamido)pyridin-2-yl)pyridine-2,6-dicarboxamide dibromide ([H(2)L(2)]Br(2)) is formed through the double alkylation of 2 with 2,6-bis(bromomethyl)pyridine. The imidazole analogues of 2 and [H(2)L(2)]Br(2) (1 and [H(2)L(1)]Br(2), respectively) have
Hanna S Abbo et al.
Molecules (Basel, Switzerland), 18(4), 4728-4738 (2013-04-24)
The tridentate ligand 2,6-bis(3,5-diphenylpyrazol-1-ylmethyl)pyridine, abbreviated as 2,6-[(3,5-ph₂pz-CH₂)₂-py], a new pyridine-pyrazole derivative, was prepared from 2,6-bis(bromomethyl)pyridine and 3,5-diphenylpyrazole. The ligand was characterized by means of elemental analyses, ATR-IR, ¹H- and ¹³C-NMR spectroscopy and single crystal X-ray crystallography. Using this ligand, a
2, 6-Bis(bromomethyl) pyridine.
Cuzan O, et al.
Acta Crystallographica Section E, Structure Reports Online, 70(1), 4-4 (2014)
Synthesis of an imidazolium-linked cyclophane from histamine.
Durmus S, et al.
Tetrahedron, 61(1), 97-101 (2005)
William Levason et al.
Dalton transactions (Cambridge, England : 2003), (23)(23), 4569-4577 (2009-06-03)
Simultaneous dropwise addition of thf/EtOH solutions of Se{(CH(2))(3)OTs}(2) and o-C(6)H(4)(CH(2)SeCN)(2) or NCSe(CH(2))(3)SeCN to a suspension of NaBH(4) in thf/EtOH at room temperature yields gram quantities of the 13- and 12-membered triselenoether macrocycles (1) and (2) respectively in high yield. The

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