99931-82-5

Basic information

• Product Name: N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE
• Synonyms: N-(4-AMINOPHENYL)-4,6-DIMETHYL-2-PYRIMIDINAMINE;N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE;(5-BROMOPYRIMIDIN-2-YL)PIPERAZINE;5-BROMO-2-(PIPERAZIN-1-YL)PYRIMIDINE;2-[N-(4-AMINOPHENYL)AMINO]-4,6-DIMETHYLPYRIMIDINE;5-Bromo-2-piperazin-1-yl-pyrim;1-(5-Bromopyrimidin-2-yl)piperazine;5-Bromo-2-piperazinopyrimidine
• CAS NO: 99931-82-5
• Molecular Formula: C₈H₁₁BrN₄
• Molecular Weight: 243.11
• Product Categories: pharmacetical;Pyrimidine;Amino;Organohalides;Halides;Pyrazines, Pyrimidines & Pyridazines
• Mol File: 99931-82-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 77 °C
• Boiling Point: 383.436 °C at 760 mmHg
• Flash Point: 185.696 °C
• Appearance: /
• Density: 1.516 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: Room temperature.
• CAS DataBase Reference: N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE(99931-82-5)
• EPA Substance Registry System: N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE(99931-82-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• Hazardous Substances Data: 99931-82-5(Hazardous Substances Data)

Usage

General Description

N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINE, also known as prodiamine, is a chemical compound commonly used as a pre-emergent herbicide to control weeds in turfgrass and landscape ornamentals. It works by inhibiting the growth of weed seeds and young seedlings, preventing them from establishing and competing with desirable plant species. Prodiamine is a white crystalline solid that is sparingly soluble in water and is typically applied as a granular formulation. It is considered to have low toxicity to mammals and has a low potential for groundwater contamination, making it a relatively safe and effective choice for weed control in various landscaping and agricultural applications. However, it is important to follow label instructions and guidelines for proper application to minimize potential environmental impacts.

InChI:InChI=1/C8H11BrN4/c9-7-5-11-8(12-6-7)13-3-1-10-2-4-13/h5-6,10H,1-4H2

Upstream product

• 20980-22-7 N-(2-pyridinyl)piperazine 
• 494772-35-9 1-[4-(5-Bromo-pyrimidin-2-yl)-piperazin-1-yl]-ethanone 
• 374930-88-8 tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate 

Downstream Products

• 99931-65-4 4-[4-(5-Bromo-pyrimidin-2-yl)-piperazin-1-yl]-1-(4-fluoro-phenyl)-butan-1-one 
• 188257-71-8 5-Bromo-2-{4-[2-(3,5-dichloro-phenyl)-3H-imidazol-4-ylmethyl]-piperazin-1-yl}-pyrimidine 
• 849021-42-7 2-(4-(5-bromopyrimidin-2-yl)piperazin-1-yl)ethanol 
• 87789-61-5 1-(5-Benzyloxy-2-pyrimidinyl)piperazine 
• 1333320-39-0 N-{2-[4-(5-benzyloxy-pyrimidin-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-2-fluoropyridine-4-carboxamide 
• 1333320-40-3 [⁽¹⁸⁾F]-N-{2-[4-(5-benzyloxy-pyrimidin-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-2-fluoropyridine-4-carboxamide 
• 1333316-46-3 N-{2-[4-(5-benzyloxy-pyrimidin-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-2-iodopyridine-4-carboxamide 
• 1333316-49-6 tert-butyl (2-{4-[5-(benzyloxy)pyrimidin-2-yl]piperazin-1-yl}-2-oxoethyl)carbamate 
• 950410-05-6 5-bromo-2-(4-ethylpiperazin-1-yl)pyrimidine 
• 1215855-15-4 4-(5-bromo-pyrimidin-2-yl)-piperazine-1-carboxylic acid (2-phenyl-benzofuran-5-yl)-amide 
• 1215855-10-9 4-(5-bromo-pyrimidin-2-yl)-piperazine-1-carboxylic acid (4-benzyloxy-phenyl)-amide 
• 1140502-22-2 5-{5-[2-(piperazin-1-yl)pyrimidin-5-yl]-1H-benzimidazol-1-yl}-3-({(1R)-1-[2-chlorophenyl]ethyl}oxy)thiophene-2-carboxamide 

Relevant articles and documents

Improvement of Aqueous Solubility of Lapatinib-Derived Analogues: Identification of a Quinolinimine Lead for Human African Trypanosomiasis Drug Development

Lapatinib, an approved epidermal growth factor receptor inhibitor, was explored as a starting point for the synthesis of new hits against Trypanosoma brucei, the causative agent of human African trypanosomiasis (HAT). Previous work culminated in 1 (NEU-1953), which was part of a series typically associated with poor aqueous solubility. In this report, we present various medicinal chemistry strategies that were used to increase the aqueous solubility and improve the physicochemical profile without sacrificing antitrypanosomal potency. To rank trypanocidal hits, a new assay (summarized in a cytocidal effective concentration (CEC50)) was established, as part of the lead selection process. Increasing the sp3 carbon content of 1 resulted in 10e (0.19 μM EC50 against T. brucei and 990 μM aqueous solubility). Further chemical exploration of 10e yielded 22a, a trypanocidal quinolinimine (EC50: 0.013 μM; aqueous solubility: 880 μM; and CEC50: 0.18 μM). Compound 22a reduced parasitemia 109 fold in trypanosome-infected mice; it is an advanced lead for HAT drug development.

The synthesis of tritiated 2-phenyl-4-[4-(2-pyrimidyl)piperazinyl]methylimidazole ([3H] NGD 94-1), a ligand selective for the dopamine D4 receptor subtype

A tritiated ligand for the dopamine D4 receptor subtype, 2-phenyl-4-[4-(2-pyrimidyl)piperazinyl]methylimidazole ([3H] NGD 94-1), was prepared in six steps starting with 3,5-dichlorobenzonitrile. NGD 94-1 was shown to have a greater t

Synthesis and anxiolytic activity of N-substituted cyclic imides (1R*,2S*3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-b icyclo[2.2.1]heptanedicarboxime (Tandospirone) and related compounds

A series of cyclic imides bearing a ω-(4-aryl and 4-heteroaryl-1-piperazinyl)alkyl moieties was synthesized and tested in vivo for anxiolytic activity. The in vitro binding affinities of these compounds were also examined for 5-HT(1A) receptor sites. Structure-activity relationships within these series are discussed. One of these compounds, (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3- bicyclo[2.2.1]heptanedicarboximide (1: tandospirone), was found to be equipotent with buspirone in its anxiolytic activity and more anxio-selective than buspirone and diazepam. Tandospirone (1) is currently undergoing clinical evaluation as a selective anxiolytic agent.