82499-03-4

Basic information

• Product Name: 2-Amino-6-bromopurine
• Synonyms: 2-AMINO-6-BROMOPURINE;6-BROMOGUANINE;d2-Amino-6-bromopurine;6-broMo-7H-purin-2-aMine;1H-Purin-2-aMine, 6-broMo-
• CAS NO: 82499-03-4
• Molecular Formula: C₅H₄BrN₅
• Molecular Weight: 214.02
• Product Categories: Purines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PurinesHeterocyclic Building Blocks
• Mol File: 82499-03-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: >350 °C(lit.)
• Boiling Point: 642.5 °C at 760 mmHg
• Flash Point: 342.4 °C
• Appearance: /
• Density: 2.14 g/cm³
• Vapor Pressure: 2.11E-16mmHg at 25°C
• Refractive Index: 1.851
• Storage Temp.: 2-8°C
• PKA: 6.58±0.20(Predicted)
• CAS DataBase Reference: 2-Amino-6-bromopurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-bromopurine(82499-03-4)
• EPA Substance Registry System: 2-Amino-6-bromopurine(82499-03-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 82499-03-4(Hazardous Substances Data)

Usage

Description

2-Amino-6-bromopurine, a 2-amino-6-halogenopurine derivative, is synthesized through the reaction between 2-amino-6-chloropurine and KX (X=Br). It has been identified as a substrate for adenine deaminase, an enzyme that plays a crucial role in the metabolic pathway of purine nucleosides. The orientations of 2-amino-6-bromopurine in the docking conformations of guanine riboswitch complexed with ABPu have been analyzed, providing insights into its interactions with biological systems.

Uses

Used in Pharmaceutical Industry:
2-Amino-6-bromopurine is used as a pharmaceutical intermediate for the development of antiviral and anticancer drugs. Its ability to act as a substrate for adenine deaminase makes it a potential candidate for the design of novel therapeutic agents targeting viral and cancerous cells.
Used in Biochemical Research:
2-Amino-6-bromopurine serves as a valuable tool in biochemical research, particularly in the study of enzyme mechanisms, nucleic acid interactions, and the development of new drugs targeting specific metabolic pathways. Its analysis in the docking conformations of guanine riboswitch complexes provides insights into the molecular recognition and binding processes, aiding in the understanding of riboswitch function and regulation.
Used in Drug Design and Development:
2-Amino-6-bromopurine is utilized in the design and development of new drugs targeting adenine deaminase and other related enzymes. Its unique chemical properties and interactions with biological systems make it a promising scaffold for the creation of innovative therapeutic agents with improved efficacy and selectivity.

InChI:InChI=1/C5H4BrN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)

Upstream product

• 21295-51-2 phosphoryl(III) bromide 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 

Downstream Products

• 131266-20-1 9-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-bromopurine 
• 131266-21-2 7-(4-acetoxy-3-acetoxymethylbutyl)-2-amino-6-bromopurine 
• 132194-22-0 2-amino-6-bromo-9-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-9H-purine 
• 515160-62-0 8-phenyl-3H-[1,2,4]triazolo[5,1-i]purin-5-ylamine 
• 515160-68-6 8-(3-fluoro-phenyl)-3H-[1,2,4]triazolo[5,1-i]purin-5-ylamine 
• 515160-64-2 8-(2-fluoro-phenyl)-3H-[1,2,4]triazolo[5,1-i]purin-5-ylamine 
• 515160-66-4 8-(2-trifluoromethyl-phenyl)-3H-[1,2,4]triazolo[5,1-i]purin-5-ylamine 
• 515160-77-7 toluene-4-sulfonic acid 2-(5-amino-8-furan-2-yl-[1,2,4]triazolo[5,1-i]purin-3-yl)-ethyl ester 
• 515160-63-1 toluene-4-sulfonic acid 2-(5-amino-8-phenyl-[1,2,4]triazolo[5,1-i]purin-3-yl)-ethyl ester 
• 515160-71-1 toluene-4-sulfonic acid 2-(5-amino-8-pyridin-2-yl-[1,2,4]triazolo[5,1-i]purin-3-yl)-ethyl ester 
• 943241-97-2 toluene-4-sulfonic acid 2-[5-amino-8-(1-oxy-pyridin-2-yl)-[1,2,4]triazolo[5,1-i]purin-3-yl]-ethyl ester 
• 515160-69-7 toluene-4-sulfonic acid 2-[5-amino-8-(3-fluoro-phenyl)-[1,2,4]triazolo[5,1-i]purin-3-yl]-ethyl ester 
• 515160-76-6 toluene-4-sulfonic acid 2-(5-amino-8-o-tolyl-[1,2,4]triazolo[5,1-i]purin-3-yl)-ethyl ester 
• 515160-65-3 toluene-4-sulfonic acid 2-[5-amino-8-(2-fluoro-phenyl)-[1,2,4]triazolo[5,1-i]purin-3-yl]-ethyl ester 

Relevant articles and documents

2-formylamino-6-halogenopurine

The present invention is directed to a method for production of a 2-amino-6-halogenopurine, a novel synthesis intermediate therefor and a method for production of said synthesis intermediate. The desired 2-amino-6-halogenopurine is an intermediate for the production of compounds useful as antiviral agents, and by using the compound of the present invention as a starting material, the 2-amino-6-halogenopurine can be produced in high yield.