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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

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

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

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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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
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
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
Synthesis of an imidazolium-linked cyclophane from histamine.
Durmus S, et al.
Tetrahedron, 61(1), 97-101 (2005)
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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