3-Bromo-5-iodopyridin-2-amine

Name: 3-Bromo-5-iodopyridin-2-amine
Brand: ChemScene
Availability: InStock
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CAS No. 697300-73-5
Cat. No. CS-W018774
Purity≥98%
MDL No.MFCD08272065

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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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3-Bromo-5-iodopyridin-2-amine|CS-W018774

Structure of 697300-73-5

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General Information

CAS No. 697300-73-5
Cat. No. CS-W018774
Purity ≥98%
MDL No. MFCD08272065
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₄BrIN₂
Molecular Weight 298.91
Synonym(s) 3-bromo-5-iodo-2-pyridinamine
SMILES NC1=C(Br)C=C(I)C=N1

Description

3-Bromo-5-iodopyridin-2-amine features a pyridine core bearing bromo and iodo substituents at meta positions relative to the amino group, enabling orthogonal functionalization. This electron-deficient heterocycle integrates readily into cross-coupling reactions, offering precise control in constructing complex pharmaceutical intermediates. The amino handle facilitates derivatization under mild conditions.

Application

3-Bromo-5-iodopyridin-2-amine serves as a versatile building block for cross-coupling reactions, enabling the construction of biaryl and heterocyclic scaffolds. Its dual halogenation pattern facilitates sequential Pd-catalyzed coupling with broad functional group tolerance. The pyridin-2-amine core provides a handle for further derivatization, while the compound exhibits excellent bench stability and ease of purification, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  20511-12-0
- ~59%
- In-stock
  
  697300-73-5
References
- Zhang, Yi; Pavlova, Olga A.; Chefer, Svetlana I.; Hall, Andrew W.; Kurian, Varughese; Brown, LaVerne L.; Kimes, Alane S.; Mukhin, Alexey G.; Horti, Andrew G. Journal of Medicinal Chemistry, 2004 , vol. 47, # 10 p. 2453 - 2465
Route2
- In-stock
  
  13534-99-1
- ~39%
- In-stock
  
  697300-73-5
References
- Gonzalez Cabrera, Diego; Douelle, Frederic; Younis, Yassir; Feng, Tzu-Shean; Le Manach, Claire; Nchinda, Aloysius T.; Street, Leslie J.; Scheurer, Christian; Kamber, Jolanda; White, Karen L.; Montagnat, Oliver D.; Ryan, Eileen; Katneni, Kasiram; Zabiulla, K. Mohammed; Joseph, Jayan T.; Bashyam, Sridevi; Waterson, David; Witty, Michael J.; Charman, Susan A.; Wittlin, Sergio; Chibale, Kelly Journal of Medicinal Chemistry, 2012 , vol. 55, # 24 p. 11022 - 11030

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 38.91
LogP 2.0309
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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3-Bromo-5-iodopyridin-2-amine

CAS No. 697300-73-5

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