3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

Name: 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid
Brand: ChemScene
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CAS No. 500011-86-9
Cat. No. CS-0046975
Purity≥98%
MDL No.MFCD08689880

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Type	HazMat Fee
Excepted Quantity	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid|CS-0046975

Structure of 500011-86-9

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General Information

CAS No. 500011-86-9
Cat. No. CS-0046975
Purity ≥98%
MDL No. MFCD08689880
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅BrClN₃O₂
Molecular Weight 302.51
Synonym(s) 5-Bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid
SMILES O=C(C1=CC(Br)=NN1C2=NC=CC=C2Cl)O

Description

This pyrazole-based scaffold integrates a bromine electrophile and a chloropyridine moiety, enabling direct coupling in cross-coupling reactions. The carboxylic acid group provides a handle for derivatization or conjugation, while the electron-deficient pyridine enhances reactivity. Bench-stable and moisture-tolerant, this compound serves as a key building block in medicinal chemistry and agrochemical synthesis.

Application

3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid serves as a versatile building block for the synthesis of functionalized heterocyclic scaffolds. Its dual halogenation (Br at C3, Cl at pyridine C3) enables sequential cross-coupling reactions under palladium catalysis. The carboxylic acid group facilitates direct derivatization or incorporation into peptide-like linkages, offering orthogonal reactivity in multi-step synthesis. Bench-stable and amenable to standard purification methods, it functions effectively in medicinal chemistry campaigns targeting kinase inhibitors and other bioactive molecules.

Synthesis

Route1
- 500011-85-8
- 124-38-9
- ~85%
- In-stock
  
  500011-86-9
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 22 p. 6274 - 6279
Route2
- 500011-85-8
- ~%
- In-stock
  
  500011-86-9
References
- WO2007/43677 A1, ; Page/Page column 490-491 ;
Route3
- 500011-88-1
- ~%
- In-stock
  
  500011-86-9
References
- Journal of Agricultural and Food Chemistry, , vol. 60, # 31 p. 7565 - 7572

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 68.01
LogP 2.3814
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

CAS No. 500011-86-9

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