6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine

Name: 6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 89167-24-8
Cat. No. CS-0043068
Purity≥97%
MDL No.MFCD09971401

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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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6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine|CS-0043068

Structure of 89167-24-8

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General Information

CAS No. 89167-24-8
Cat. No. CS-0043068
Purity ≥97%
MDL No. MFCD09971401
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃BrN₄
Molecular Weight 199.01
Synonym(s) 6-BROMO[1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE
SMILES BrC1=CN2C(N=C1)=NC=N2

Description

6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine is a heterocyclic building block featuring a bromine substituent at the 6-position of a fused triazolopyrimidine core. This electron-deficient scaffold integrates readily into C–C and C–heteroatom coupling reactions, enabling efficient access to functionalized purine analogs. The bromine moiety offers high reactivity in palladium-catalyzed transformations, while the rigid planar structure enhances stability under standard reaction conditions.

Application

6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine serves as a versatile heterocyclic building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions for C–C bond formation. Its bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the electron-deficient triazolopyrimidine core enhances functional group tolerance and stability under standard reaction conditions. The compound functions as a key scaffold for constructing bioactive molecules and is well-suited for parallel synthesis campaigns.

Synthesis

Route1
- 2065-75-0
- In-stock
  
  61-82-5
- ~76%
- In-stock
  
  89167-24-8
References
- MERZ PHARMA GMBH and CO. KGAA; HENRICH, Markus; WEIL, Tanja; HECHENBERGER, Mirko; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; ERDMANE, Elina; SMITS, Gints Patent: WO2011/15343 A1, 2011 ; Location in patent: Page/Page column 39-40 ; WO 2011/015343 A1
Route2
- In-stock
  
  61-82-5
- 2065-75-0
- ~81%
- In-stock
  
  89167-24-8
References
- Salgado, Antonio; Varela, Carmen; Collazo, Ana Maria Garcia; Pevarello, Paolo Magnetic Resonance in Chemistry, 2010 , vol. 48, # 8 p. 614 - 622

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 43.08
LogP 0.8868
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Building Blocks Skeleton Aromatic heterocycle compounds Triazole compounds

Key Words

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6-Bromo-[1,2,4]triazolo[1,5-a]pyrimidine

CAS No. 89167-24-8

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