29366-73-2

Basic information

• Product Name: 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine
• Synonyms: 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine;6-(4-Nitrophenyl)-1,3,5-triazine-2,4-diamine;1,3,5-Triazine-2,4-diaMine, 6-(4-nitrophenyl)-
• CAS NO: 29366-73-2
• Molecular Formula: C₉H₈N₆O₂
• Molecular Weight: 232.1988
• Mol File: 29366-73-2.mol

Chemical Properties

• Melting Point: 330-331 °C
• Boiling Point: 588.7°Cat760mmHg
• Flash Point: 309.8°C
• Appearance: /
• Density: 1.539g/cm³
• Vapor Pressure: 7.78E-14mmHg at 25°C
• Refractive Index: 1.729
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine(29366-73-2)
• EPA Substance Registry System: 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine(29366-73-2)

Safety Data

• Hazardous Substances Data: 29366-73-2(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Applications:
2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine is used as a herbicide for controlling broadleaf weeds in various crops such as wheat, maize, and sorghum. Its effectiveness in managing these weeds helps protect and enhance crop yields.
Used in Research Applications:
Due to its reactivity and potential biological activity, 2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine is utilized in research settings to explore its properties and possible applications in various scientific fields.
Used in Pharmaceutical Applications:
2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine's unique structure and reactivity make it a candidate for pharmaceutical development. It is used in the synthesis of new drugs and as a building block for the creation of novel therapeutic agents.
Used in Chemical Synthesis:
2,4-Diamino-6-(4-nitrophenyl)-1,3,5-triazine serves as an intermediate in the synthesis of other chemical compounds, contributing to the development of new materials and products across different industries.

InChI:InChI=1/C9H8N6O2/c10-8-12-7(13-9(11)14-8)5-1-3-6(4-2-5)15(16)17/h1-4H,(H4,10,11,12,13,14)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 127099-85-8 N-Cyanoguanidine 
• 619-72-7 4-nitrobenzonitrile 

Downstream Products

• 186834-91-3 N-[4-Isobutyrylamino-6-(4-nitro-phenyl)-[1,3,5]triazin-2-yl]-isobutyramide 
• 1197159-91-3 4-(4,6-dimorpholin-4-yl-1,3,5-triazin-2-yl)aniline 
• 1197160-78-3 PKI-587 
• 15074-26-7 2,4-Diamino-6-(4-aminophenyl)-1,3,5-triazine 

Relevant articles and documents

New and Practical Synthesis of Gedatolisib

A new, practical, and convergent synthetic route of gedatolisib, an antitumor agent, is developed on a hectogram scale which avoids the Pd coupling method. The key step is adopting 6-(4-nitrophenyl)-1,3,5-triazine-2,4-diamine and 2,2′-dichlorodiethyl ether to prepare the key 4,4′-(6-(4-nitrophenyl)-1,3,5-triazine-2,4-diyl)dimorpholine in 77% yield and 98.8% purity. Gedatolisib is obtained in 48.6% yield over five simple steps and 99.3% purity (HPLC). Purification methods of the intermediates and the final product involved in the route are given.

Gedatolisib intermediates for preparation of (by machine translation)

The invention belongs to the organic synthesis and bulk drug intermediate preparation field, in particular to a method for preparing Gedatolisib, key intermediate and a key intermediate in the preparation method. The nitrobenzene nitrile and dicyanodiamine polyisobutylene triazine cyclization, morpholine link guan huan, hydrogenation of nitro reduction to obtain 4 - (4, 6 - II morpholino - 1, 3, 5 - triazine - 2 - yl) aniline; 4 - oxo-piperidine - 1 - carboxylic acid tert-butyl and dimethylamine salt by addition, de-Boc protecting group, amide, hydrogenation of nitro reduction to get new compounds (4 - aminophenyl) (4 - (dimethyl amino) piperidine - 1 - yl) methyl ketone; adopts the one-pot synthesis, (4, 6 - II morpholino - 1, 3, 5 - triazine - 2 - yl) aniline and chloromethane acid ester after the reaction, then adding (4 - aminophenyl) (4 - (dimethyl amino) piperidine - 1 - yl) methanone, to finally obtain the Gedatolisib. This preparation method has the advantages of easy availability of raw materials, process is simple, easy to operate, high yield and low cost and the like. (by machine translation)

Microwave-assisted one-pot tandem reactions for direct conversion of primary alcohols and aldehydes to triazines and tetrazoles in aqueous media

(Chemical Equation Presented) A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford high yields of the corresponding triazines and tetrazoles, including the α-amino- and dipeptidyl tetrazoles in high optical purity.

Green synthesis and self-association of 2,4-diamino-1,3,5-triazine derivatives

2,4-Diamino-1,3,5-triazines have been prepared by reaction of dicyandiamide with nitriles under microwave irradiation, a method that can be considered as a green procedure due to the reduction in the use of solvents during synthesis and purification, the short reaction time and the simplicity of the procedure. The structures have been confirmed in solution by NMR spectroscopy. Variable temperature experiments have been used to calculate the free energy of activation for rotation about the amino-triazine bond. The crystal structures of three 2,4-diamino-6-R-1,3,5-triazine derivatives (3a: R = phenyl, 3i: R = 1-piperidino and 3g: R = 1-phenylpyrazol-3-yl) have been determined by X-ray analysis. The N-H...N interactions change from structure to structure, resulting in a variation from pseudo-honeycomb networks to corrugated rosette layers.

Microwave-assisted clean synthesis of 6-aryl-2,4-diamino-1,3,5-triazines in [bmim][PF6]

An efficient and green approach was developed to prepare 6-aryl-2,4-diamino-1,3,5-triazines from corresponding arylnitriles and dicyanodiamide in ionic liquid [bmim][PF6] under computer-controlled microwave irradiation. Particularly valuable features of this method included the short reaction time, good yield, convenient operation and eco-friendly solvent.

Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions

A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in modest to high yields. The one-pot tandem reactions were conducted in water media, and the products were obtained simply by extraction or filtration.

Model Systems for Flavoenzyme Activity. Regulation of Flavin Recognition via Modulation of Receptor Hydrogen-Bond Donor-Acceptor Properties

We have synthesized a new family of receptors for flavins based on 6-aryl-2,4-(acyldiamino)-s-triazines. In these synthetic hosts, systematic variation of the spatially remote substituents on the 6-aryl ring alters the hydrogen-bond-donating abilities of the amide functionality and the hydrogen-bond-accepting properties of the triazine N(3). This variation results in a strong modulation of the efficiency of flavin binding, with association constants for the receptor flavin complexes ranging over an 8-fold range.