823-89-2

Basic information

• Product Name: 5-BROMO-2-HYDRAZINOPYRIMIDINE
• Synonyms: (5-BROMO-PYRIMIDIN-2-YL)HYDRAZINE;5-BROMO-2-HYDRAZINOPYRIMIDINE;2-(5-broMopyriMidin-2-yl)hydrazine;5-Bromo-2-hydrazino-1,3-diazine, (5-Bromopyrimidin-2-yl)hydrazine;(5-Bromopyrimidin-2-yl)hydrazine(HCl);(5-bromo-2-pyrimidinyl)hydrazine
• CAS NO: 823-89-2
• Molecular Formula: C₄H₅BrN₄
• Molecular Weight: 189.01
• Product Categories: Organohalides;Pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 823-89-2.mol

Chemical Properties

• Melting Point: 205-207(dec.)
• Boiling Point: 354.7ºC at 760 mmHg
• Flash Point: 168.3ºC
• Appearance: /
• Density: 1.915g/cm3
• Vapor Pressure: 3.29E-05mmHg at 25°C
• Refractive Index: 1.711
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 5.42±0.20(Predicted)
• CAS DataBase Reference: 5-BROMO-2-HYDRAZINOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-HYDRAZINOPYRIMIDINE(823-89-2)
• EPA Substance Registry System: 5-BROMO-2-HYDRAZINOPYRIMIDINE(823-89-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 823-89-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-hydrazinopyrimidine is used as a building block for the synthesis of various pharmaceutical compounds. Its hydrazine functional group makes it a valuable precursor in the development of drug molecules, contributing to the creation of new therapeutic agents.
Used in Research and Development:
In the scientific community, 5-Bromo-2-hydrazinopyrimidine is utilized as a reagent in organic synthesis, facilitating the exploration and development of new chemical entities. Its unique properties allow researchers to investigate novel applications and reactions in organic chemistry.
Used in Organic Synthesis:
5-Bromo-2-hydrazinopyrimidine is employed as a reagent in organic synthesis processes, where its functional groups enable the formation of diverse organic compounds. This versatility is crucial for advancing the field of organic chemistry and discovering new synthetic pathways.

InChI:InChI=1/C4H5BrN4/c5-3-1-7-4(9-6)8-2-3/h1-2H,6H2,(H,7,8,9)

Upstream product

• 32779-36-5 5-Bromo-2-chloropyrimidine 

Downstream Products

• 1272659-59-2 (E)-2-(3-acetylbenzylidene)-1-(5-bromopyrimidin-2-yl)hydrazine 
• 1272659-58-1 (E)-2-(4-methoxybenzylidene)-1-(5-bromopyrimidin-2-yl)hydrazine 
• 1272659-60-5 (E)-2-(4-carboxybenzylidene)-1-(5-bromopyrimidin-2-yl)hydrazine 
• 1272659-62-7 (E)-2-(3,4-dimethoxybenzylidene)-1-(5-bromopyrimidin-2-yl)hydrazine 
• 1312952-12-7 (E)-2-(2-benzylidenehydrazinyl)-5-bromopyrimidine 
• 1233537-70-6 5-bromo-2-(5-(4-nitrophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-85-9 5-bromo-2-(3-phenyl-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-87-1 5-bromo-2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-89-3 5-bromo-2-(5-(4-bromophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-91-7 2-(3,5-bis(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-5-bromopyrimidine 
• 1400673-93-9 5-bromo-2-(3-(4-bromophenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-95-1 5-Bromo-2-(3-(4-bromophenyl)-5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-97-3 5-bromo-2-(3-(4-chlorophenyl)-5-p-tolyl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 
• 1400673-99-5 5-bromo-2-(3-(4-chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine 

Relevant articles and documents

Scaffold-Hopping Strategy on a Series of Proteasome Inhibitors Led to a Preclinical Candidate for the Treatment of Visceral Leishmaniasis

There is an urgent need for new treatments for visceral leishmaniasis (VL), a parasitic infection which impacts heavily large areas of East Africa, Asia, and South America. We previously reported on the discovery of GSK3494245/DDD01305143 (1) as a preclinical candidate for VL and, herein, we report on the medicinal chemistry program that led to its identification. A hit from a phenotypic screen was optimized to give a compound with in vivo efficacy, which was hampered by poor solubility and genotoxicity. The work on the original scaffold failed to lead to developable compounds, so an extensive scaffold-hopping exercise involving medicinal chemistry design, in silico profiling, and subsequent synthesis was utilized, leading to the preclinical candidate. The compound was shown to act via proteasome inhibition, and we report on the modeling of different scaffolds into a cryo-EM structure and the impact this has on our understanding of the series' structure-activity relationships.

Activating Pyrimidines by Pre-distortion for the General Synthesis of 7-Aza-indazoles from 2-Hydrazonylpyrimidines via Intramolecular Diels-Alder Reactions

Pyrimidines are almost unreactive partners in Diels-Alder cycloadditions with alkenes and alkynes, and only reactions under drastic conditions have previously been reported. We describe how 2-hydrazonylpyrimidines, easily obtained in two steps from commercially available 2-halopyrimidines, can be exceptionally activated by trifluoroacetylation. This allows a Diels-Alder cycloaddition under very mild reaction conditions, leading to a large diversity of aza-indazoles, a ubiquitous scaffold in medicinal chemistry. This reaction is general and scalable and has an excellent functional group tolerance. A straightforward synthesis of a key intermediate of Bayer's Vericiguat illustrates the potential of this cycloaddition strategy. Quantum mechanical calculations show how the simple N-trifluoroacetylation of 2-hydrazonylpyrimidines distorts the substrate into a transition-state-like geometry that readily undergoes the intramolecular Diels-Alder cycloaddition.

Synthesis, characterization and pharmacological study of 4,5-dihydropyrazolines carrying pyrimidine moiety

A series of 5-bromo-2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)pyrimidine were prepared under conventional heating as well as microwave reaction condition. The newly synthesized compounds were characterized on the basis of elemental, spectral and single crystal X-ray studies. These new compounds were screened for their antioxidant, anti-inflammatory and analgesic activities. Some of these compounds exhibited potent biological activities compared to the standard drug.

Synthesis of [1,2,4]-triazolo[1,5-a]pyrimidines by Dimroth rearrangement of [1,2,4]-triazolo[4,3-a]pyrimidines: A theoretical and NMR study

Novel [1,2,4]-triazolo-[1,5-a]pyrimidine derivatives were prepared by oxidative cyclization of suitable N-benzylidene-N′-pyrimidin-2-yl hydrazine precursors, followed by a Dimroth rearrangement. Reaction of 6-bromo-[1,2,4]-triazolo-[4,3-a]pyrimidines with

Substituted Triazolo-Pyrimidine Compounds

The present invention relates to substituted triazolo-pyrimidine compounds and methods of synthesizing these compounds. The present invention also relates to pharmaceutical compositions containing substituted triazolo-pyrimidine compounds and methods of t