18264-75-0

Basic information

• Product Name: N-nitrocarbazamidine
• Synonyms: N-nitrocarbazamidine;[(aminocarbohydrazonoyl)amino]-hydroxy-oxo-azanium;1-Amino-2-nitroguanidine;1-Amino-3-nitroguanidine;Nitroaminoguanidine
• CAS NO: 18264-75-0
• Molecular Formula: CH₅N₅O₂
• Molecular Weight: 119.0827
• EINECS: 242-139-1
• Mol File: 18264-75-0.mol
• Article Data: 18

Chemical Properties

• Melting Point: 187.8°C
• Boiling Point: 222.31°C (rough estimate)
• Flash Point: 154.8°C
• Appearance: /
• Density: 2.1g/cm³
• Refractive Index: 1.6000 (estimate)
• Water Solubility: 2.684g/L(20.96 oC)
• CAS DataBase Reference: N-nitrocarbazamidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-nitrocarbazamidine(18264-75-0)
• EPA Substance Registry System: N-nitrocarbazamidine(18264-75-0)

Safety Data

• Hazardous Substances Data: 18264-75-0(Hazardous Substances Data)

Usage

Description

N-nitrocarbazamidine is a yellow crystalline solid that belongs to the class of nitro compounds. It is insoluble in water and stable under normal conditions. This chemical compound is known for its versatility as a building block in the development of various functional materials, such as dyes and polymers. Although it is considered to have low toxicity, care should be taken when handling it, as it can release toxic fumes when heated or burned.

Uses

Used in Organic Synthesis:
N-nitrocarbazamidine is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions. Its unique properties make it a valuable component in the creation of complex organic molecules.
Used in Pharmaceutical Production:
As a precursor in the production of pharmaceuticals, N-nitrocarbazamidine plays a crucial role in the development of new drugs. Its chemical structure allows it to be a key intermediate in the synthesis of various medicinal compounds.
Used in Agrochemical Production:
N-nitrocarbazamidine also serves as a precursor in the production of agrochemicals, contributing to the development of effective products for agricultural applications.
Used in the Development of Functional Materials:
N-nitrocarbazamidine is a versatile building block in the creation of functional materials such as dyes and polymers. Its incorporation into these materials can enhance their properties and performance in various industries.

InChI:InChI=1/CH6N5O2/c2-1(4-3)5-6(7)8/h3H2,(H,7,8)(H3,2,4,5)/q+1

Upstream product

• 2986-25-6 methyl nitrocarbamimidothioate 
• 556-88-7 nitroguanidine 
• 5458-83-3 N-butyl-N'-nitro-guanidine 
• 7732-18-5 water 
• 7803-57-8 hydrazine hydrate 
• 556-88-7 2-nitroguanidine 
• 302-01-2 hydrazine 
• 651322-68-8 1,2-dinitroguanidine 
• 39197-62-1 N-ethyl-N'-nitroguanidine 
• 4245-76-5 N-Methyl-N'-nitroguanidine 
• 70-25-7 N-methyl-N''-nitro-N-nitrosoguanidine 
• 2986-25-6 S-methyl-N-nitroisothiourea 
• 62154-79-4 nitro-azidocarboxamidine 

Downstream Products

• 5347-94-4 furfural-(nitrocarbamimidoyl-hydrazone) 
• 42216-32-0 N-(N''-nitrocarbamimidoylamino)benzamide 
• 109047-25-8 N-(2-chloro-1-phenyl-ethylidenamino)-N'-nitro-guanidine 
• 109098-88-6 N-(2-bromo-1-phenyl-ethylidenamino)-N'-nitro-guanidine 
• 100128-66-3 N-nitro-N'-(3t-phenyl-1-methyl-allylidenamino)-guanidine 
• 35957-61-0 N-(1-methyl-2-phenyl-ethylidenamino)-N'-nitro-guanidine 
• 98488-88-1 N-(3,4-dihydroxy-benzylidenamino)-N'-nitro-guanidine 
• 51707-10-9 3-[(nitrocarbamimidoyl-hydrazono)-methyl]-rifamycin 
• 111444-64-5 1,2-Dibenzoylethan-bis-nitroguanylhydrazon 
• 5347-98-8 2-(2'-nitrobenzylidene)-N'-nitrohydrazinecarboximidamide 

Relevant articles and documents

A simple method for the preparation of 3,5-dinitrimino-1,2,4-triazole and its salts

The reaction of 2-methyl-1-nitrоisothiourea with hydrazine in the presence of alkali metal bicarbonates (carbonates) resulted in the formation of 3,5-dinitrimino-1,2,4-triazole salts. The same salts were also formed by a reaction of 2-methyl-1-nitrоisothiourea with alkali metal salts of 4-nitrоsemicarbazide. This represents the first synthesis and characterization of the high-energy 3,5-dinitrimino-1,2,4- triazole, which can be readily isolated by treatment of its disodium salt with HCl.

Synthesis and insecticidal activities of 1,5-disubstituted-1,3,5- hexahydrotriazine-2-N-nitroimines

By extracting active moieties from typical insecticides and recombining to a same molecule, a series of novel title compounds were designed and synthesized as shown in Scheme 1. The structures of all compounds were confirmed by IR, 1H NMR, MS, and elemental analysis. The preliminary bioassay showed that the partial target compounds gave 90% mortality against Tetranychus cinnabarnus at 500 mg/L.

Divergent Synthesis of Substituted Amino-1,2,4-triazole Derivatives

A divergent efficient assembly of disubstituted 1,2,4-triazoles was established by cyclization of readily accessible N ′-nitro-2-hydrocarbylidene-hydrazinecarboximidamides with moderate to excellent yields under mild reaction conditions. This divergent synthetic strategy was achieved simply by varying the reaction conditions. Under acidic conditions, amino-1,2,4-triazoles were obtained by an intramolecular redox reaction involving the NO 2group. Control experiments and DFT studies revealed that this transformation proceeds via an intramolecular 1,3-hydride transfer pathway leading to HNO 2elimination. Under neutral conditions with water as the solvent, nitroimino-1,2,4-triazoles were obtained by oxidative intramolecular annulation under air.

Synthesis, insecticidal and fungicidal activities of methyl 2-(methoxyimino)-2-(2-((1-(N′-nitrocarbamimidoyl)-2-hydrocarbylidene-hydrazinyl)methyl)phenyl)acetates

N′-Nitro-2-hydrocarbylidenehydrazinecarboximidamides and methoxyacrylates are two types of important agrochemicals. By combining their key fragments into one framework, a series of the title compounds was designed and synthesized. Some of these compounds have shown excellent insecticidal activities for aphides, for example, the LC50 values of compounds 6-06, 6-11 and 6-19 against M. perslcae and H. amygdale were found to be 1.9/14.4, 13.4/1.5 and 0.3/38.4 mg L-1 respectively. They were also effective against the mycelium growth of B. cinerea in vitro. Compound 6-04 could control (～100%) cucumber anthrax and rice blast at 100 mg L-1 in vivo, and inhibit the spore germination (～100%) of vegetable gray mold at 6.25 mg L-1. These compounds could be considered as potential insecticidal or fungicidal candidates for crop protection. The results of structure-activity relationship (SAR) studies are discussed.