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

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

Downstream Products

• 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 
• 210880-92-5 clothianidine 
• 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.

Production of compounds

Provided is a method for producing a compound represented by formula (2), or a salt thereof, by reacting ammonia with formaldehyde so as to obtain a mixture that contains a compound represented by formula (8), and then mixing the obtained mixture that contains the compound represented by formula (8) with a compound represented by formula (1), or a salt thereof, in the presence of a base.

METHOD FOR NITRATING ISOUREA

An object of the present invention is to industrially advantageously produce N-nitroisoureas or a salt thereof which is useful as a synthetic intermediate for pharmaceuticals and pesticides. The present invention relates to a process for producing a compound represented by the formula (2): wherein R1, R2 and R3 are as defined below, or a salt thereof, which comprises reacting a compound represented by the formula (1): wherein R1 represents an optionally substituted straight-chain or branched C1 to C6 alkyl group, R2 and R3 are the same or different and represent an optionally substituted straight-chain or branched C1 to C6 alkyl group, a cycloalkyl group or a substituted aryl group, or R2 and R3 simultaneously represent a hydrogen atom, or a salt thereof with a nitrating agent in the presence of sulfur trioxide.