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498181

Sigma-Aldrich

2-Chloro-5-iodopyridine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H3ClIN
CAS Number:
69045-79-0
Molecular Weight:
239.44
MDL number:
MFCD01863635
UNSPSC Code:
12352100
PubChem Substance ID:
24873177
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

95-98 °C (lit.)

functional group

chloro
iodo

SMILES string

Clc1ccc(I)cn1

InChI

1S/C5H3ClIN/c6-5-2-1-4(7)3-8-5/h1-3H

InChI key

QWLGCWXSNYKKDO-UHFFFAOYSA-N

Related Categories

General description

2-Chloro-5-iodopyridine is a halo-substituted pyridine.

Application

2-Chloro-5-iodopyridine may be used as a reagent in the multi-step synthesis of (±)-epibatidine.
It may be used in the synthesis of:
  • 2-Chloro-5-phenylpyridine via Suzuki coupling reaction with phenylboronic acid dimethyl ester.
  • Exo-5- and exo-6- (6′-chloro-3′-pyridyl)-2-azabicyclo[2.2.1]heptanes via Heck coupling reaction with N-protected 2-azabicyclo[2.2.1]hept-5-enes.
  • Substituted diaryliodonium salts.
  • 3-Exo-5′-(2′-Chloropyridinyl)-8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octane.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

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Certificates of Analysis (COA)

Lot/Batch Number
08828BH
02312BH
06211AE
07227TD
10910MA

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A short and efficient total synthesis of (?)-epibatidine.
A short and efficient total synthesis of (?)-epibatidine.
Zhang C and Trudell ML.
The Journal of Organic Chemistry, 61(20), 7189-7191 (1996)
Synthesis of epibatidine isomers: Reductive Heck coupling of 2-azabicyclo [2.2.1] hept-5-ene derivatives.
Cox CD and Malpass JR
Tetrahedron, 55(40), 11879-11888 (1999)
Synthesis of 5-Substituted 2,2'-Bipyridines from Substituted 2-Chloropyridines by a Modified Negishi Cross-Coupling Reaction.
Lutzen A and Hapke M.
European Journal of Organic Chemistry, 2002(14), 2292-2297 (2002)
High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides.
Bielawski M and Olofsson B
Chemical Communications (Cambridge, England), 24, 2521-2523 (2007)
Syntheses of new open-ring and homo-epibatidine analogues from tropinone.
Olivo HF, et al.
The Journal of Organic Chemistry, 64(13), 4966-4968 (1999)

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