57538-27-9

Basic information

• Product Name: O-Methyl-N-nitroisourea
• Synonyms: O-Methyl-N-nitroisourea;2-Methyl-1-nitroisourea;NSC 88717
• CAS NO: 57538-27-9
• Molecular Formula: C₂H₅N₃O₃
• Molecular Weight: 119.0794
• Mol File: 57538-27-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• PKA: 3.18±0.50(Predicted)
• CAS DataBase Reference: O-Methyl-N-nitroisourea(CAS DataBase Reference)
• NIST Chemistry Reference: O-Methyl-N-nitroisourea(57538-27-9)
• EPA Substance Registry System: O-Methyl-N-nitroisourea(57538-27-9)

Safety Data

• Hazardous Substances Data: 57538-27-9(Hazardous Substances Data)

Usage

General Description

O-Methyl-N-nitroisourea is a highly toxic and potentially explosive chemical compound that is primarily used as a pesticide and herbicide. It is a white crystalline solid with a strong odor and is soluble in water and organic solvents. O-Methyl-N-nitroisourea is known to be highly reactive and can easily decompose, releasing toxic fumes and heat. It is a potent inhibitor of the enzyme acetolactate synthase, which is essential for the growth of plants, making it an effective herbicide. However, due to its extreme toxicity and potential for explosive decomposition, O-Methyl-N-nitroisourea carries significant risks and requires careful handling and storage.

InChI:InChI=1/C2H6N3O3/c1-8-2(3)4-5(6)7/h1H3,(H2,3,4)(H,6,7)/q+1

Upstream product

• 57-13-6 urea 
• 616-38-6 carbonic acid dimethyl ester 
• 29427-58-5 O-methylisourea hemisulfate 
• 24285-39-0 O-methylisourea hydrosulfate 
• 2440-60-0 2-methyl-isourea 
• 77-78-1 dimethyl sulfate 
• 24285-39-0 O-methylisourea hemisulfate 

Downstream Products

• 210880-92-5 clothianidine 
• 255708-80-6 N,O-dimethyl-N'-nitroisourea 
• 4245-76-5 N-methyl-N'-nitroguanidine 
• 187149-02-6 N-(2-chlorothiazol-5-ylmethyl)-O-methyl-N'-nitroisourea 
• 255708-80-6 N,O-dimethyl-N'-nitroisourea 
• 132718-70-8 Boc-D-Har(NO2)-OH 
• 67396-06-9 C₁₄H₂₁N₅O₆S 
• 2149-70-4 N^ω-nitro-L-arginine 

Relevant articles and documents

A novel and practical method for the synthesis of dinotefuran through Michael addition of nitromethane to diethyl maleate

A novel and practical synthesis of dinotefuran 1, featuring a new access to it from known key intermediate (tetrahydrofuran-3-yl)-methanamine 5, has been achieved through Michael addition reaction of nitromethane to diethyl maleate in 6 steps with 45.5% total yield. This synthesis is scalable and hence has high potential for application to further synthetic elaboration on such new neonicotinoid insecticide dinotefuran 1.

A synthetic method of the dinotefuran (by machine translation)

The invention discloses a method for synthesis of dinotefuran, to γ - butyrolactone as raw materials, by Aldol condensation, also the original two-step by the reaction of 3 - hydroxy methyl tetrahydrofuran, then by the Gabriel synthesis of 3 - tetrahydrofuran methyl amine, dimethyl carbonate (DMC) as methylation reagent with the urea synthesis O - methyl isourea, re-nitration synthetic O - methyl - N - nitro-isourea, then with the methylamine reaction synthesis of 1, 3 - dimethyl - 2 - nitro-isourea, final 3 - tetrahydrofuran methylamine with 1, 3 - dimethyl - 2 - nitro-isourea through SN2 Bimolecular nucleophilic substitution reaction, one-step synthesis of dinotefuran. The present invention uses non of dimethyl carbonate as the methylating reagent, the methylation reaction yield ≥ 95%, O - methyl isourea content ≥ 96%, the by-product is carbon dioxide and methanol, process and environmental protection, the overall yield of the dinotefuran ≥ 50%. Synthetic method of this invention to reduce the production cost at the same time, with three wastes, after treatment is simple, the advantages of the environment friendly, and is suitable for industrial production, bring about significant economic benefits. (by machine translation)

PROCESS FOR PRODUCTION OF O-METHYL-N-NITROISOUREA

Disclosed is an industrially advantageous process for producing O-methyl-N-nitroisourea. Disclosed is a process for obtaining O-methyl-N-nitroisourea represented by the following chemical formula (1) or a salt thereof in a high yield by performing the nitration of O-methylisourea represented by the following chemical formula (2) or a salt thereof with nitrating agents in the presence of fuming sulfuric acid.