5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine

Name: 5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 923595-58-8
Cat. No. CS-W006028
Purity≥97%
MDL No.MFCD13193346

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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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5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine|CS-W006028

Structure of 923595-58-8

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General Information

CAS No. 923595-58-8
Cat. No. CS-W006028
Purity ≥97%
MDL No. MFCD13193346
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃ClIN₃
Molecular Weight 279.47
Synonym(s) None
SMILES ClC2=NC1=C(C=N[N]1C=C2)I

Description

5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine features a fused heterocyclic core with complementary halogen handles: a chlorine at C5 and an iodine at C3. This arrangement enables selective cross-coupling reactions in late-stage functionalization, particularly in the synthesis of complex pyrazolopyrimidine-based pharmaceuticals and agrochemicals. The electron-deficient scaffold supports efficient palladium-catalyzed transformations under mild conditions.

Application

5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine serves as a versatile heterocyclic building block for late-stage functionalization in medicinal chemistry. The orthogonal reactivity of chlorine and iodine enables sequential cross-coupling transformations under palladium catalysis, facilitating the construction of complex pyrazolopyrimidine scaffolds. Bench-stable and compatible with standard purification methods, it functions reliably in Suzuki-Miyaura, Stille, and Buchwald-Hartwig reactions, supporting efficient diversification of bioactive molecules.

Synthesis

Route1
- In-stock
  
  29274-24-6
- ~%
- In-stock
  
  923595-58-8
References
- WO2007/13673 A1, ; Page/Page column 31 ; WO 2007/013673 A1

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

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Computational Chemistry Data

TPSA 30.19
LogP 1.9873
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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5-Chloro-3-iodopyrazolo[1,5-a]pyrimidine

CAS No. 923595-58-8

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