3-Bromo-2-iodopyridine

Name: 3-Bromo-2-iodopyridine
Brand: ChemScene
Availability: InStock
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CAS No. 408502-43-2
Cat. No. CS-0060370
Purity≥97%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 408502-43-2

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General Information

CAS No. 408502-43-2
Cat. No. CS-0060370
Purity ≥97%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃BrIN
Molecular Weight 283.89
Synonym(s) 2-iodo-3-bromopyridine
SMILES C1=CC(=C(I)N=C1)Br

Description

3-Bromo-2-iodopyridine features a dual halogen substitution pattern on the pyridine ring, enabling selective cross-coupling reactions. The bromo group at C3 and iodo group at C2 offer orthogonal reactivity for sequential functionalization. This molecule serves as a key intermediate in the synthesis of bioactive heterocycles and pharmaceutical scaffolds.

Application

3-Bromo-2-iodopyridine serves as a versatile diaryl building block in cross-coupling chemistry, enabling efficient access to biaryl scaffolds via Pd-catalyzed reactions. The orthogonal halogen reactivity allows sequential functionalization—bromine engages in Suzuki or Stille couplings, while iodine facilitates rapid Negishi or Sonogashira transformations. Its bench-stable crystalline form and predictable regioselectivity make it ideal for iterative synthesis of complex heterocycles and pharmaceutical intermediates.

Synthesis

Route1
- 13534-89-9
- ~72%
- In-stock
  
  408502-43-2
References
- Cottet, Fabrice; Marull, Marc; Lefebvre, Olivier; Schlosser, Manfred European Journal of Organic Chemistry, 2003 , # 8 p. 1559 - 1568
Route2
- In-stock
  
  626-55-1
- ~68%
- In-stock
  
  408502-43-2
References
- Imahori; Uchiyama; Sakamoto; Kondo Chemical Communications, 2001 , # 23 p. 2450 - 2451
Route3
- In-stock
  
  626-55-1
- ~84%
- In-stock
  
  89167-19-1
- In-stock
  
  408502-43-2
References
- Snegaroff, Katia; Nguyen, Tan Tai; Marquise, Nada; Halauko, Yury S.; Harford, Philip J.; Roisnel, Thierry; Matulis, Vadim E.; Ivashkevich, Oleg A.; Chevallier, Floris; Wheatley, Andrew E. H.; Gros, Philippe C.; Mongin, Florence Chemistry - A European Journal, 2011 , vol. 17, # 47 p. 13284 - 13297

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 12.89
LogP 2.4487
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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3-Bromo-2-iodopyridine

CAS No. 408502-43-2

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