5-Bromo-7H-pyrrolo[2,3-d]pyrimidine

Name: 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 175791-49-8
Cat. No. CS-W019834
Purity≥95%
MDL No.MFCD01877574

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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-Bromo-7H-pyrrolo[2,3-d]pyrimidine|CS-W019834

Structure of 175791-49-8

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General Information

CAS No. 175791-49-8
Cat. No. CS-W019834
Purity ≥95%
MDL No. MFCD01877574
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₄BrN₃
Molecular Weight 198.02
Synonym(s) 5-Bromo-7H-pyrrolo[2,3-d]pyrimidine; 5-Bromopyrrolopyrimidine
SMILES BrC1=CNC2=NC=NC=C21

Description

5-Bromo-7H-pyrrolo[2,3-d]pyrimidine features a brominated pyrrolopyrimidine core with high electron deficiency, enabling direct functionalization in cross-coupling reactions. This bench-stable heterocycle integrates efficiently into kinase inhibitor scaffolds and other bioactive molecules, offering enhanced reactivity and structural rigidity for medicinal chemistry applications.

Application

5-Bromo-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile building block in heterocyclic synthesis, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, facilitating the construction of biologically relevant scaffolds. Its stability under standard reaction conditions and compatibility with diverse functional groups make it a practical choice for medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  271-70-5
- ~40%
- In-stock
  
  175791-49-8
References
- Sakamoto, Takao; Kondo, Yoshinori; Sato, Shuichiroh; Yamanaka, Hiroshi Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 5 p. 459 - 464

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-H312-H332
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 41.57
LogP 1.7204
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrrole compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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5-Bromo-7H-pyrrolo[2,3-d]pyrimidine

CAS No. 175791-49-8

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