24914-58-7

Basic information

• Product Name: N-(2,4-dinitrophenyl)-O-methylhydroxylamine
• Synonyms: N-(2,4-dinitrophenyl)-O-methylhydroxylamine
• CAS NO: 24914-58-7
• Molecular Weight: 213.15
• Mol File: 24914-58-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(2,4-dinitrophenyl)-O-methylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-dinitrophenyl)-O-methylhydroxylamine(24914-58-7)
• EPA Substance Registry System: N-(2,4-dinitrophenyl)-O-methylhydroxylamine(24914-58-7)

Safety Data

• Hazardous Substances Data: 24914-58-7(Hazardous Substances Data)

Upstream product

• 51348-06-2 N-(2,4-dinitrophenyl)hydroxylamine 
• 77-78-1 dimethyl sulfate 
• 67-62-9 O-Methylhydroxylamin 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 76215-45-7 bis(2,4-dinitrophenyl) phoshate pyridinium salt 
• 119-27-7 2,4-dinitroanisole 
• 2486-07-9 2,4-dinitrophenyl phenyl ether 
• 593-56-6 N-methoxylamine hydrochloride 

Downstream Products

• 117538-17-7 N-methoxy-N-(2,4,6-trinitrophenyl)aminyl radical 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 51348-04-0 N,O-dimethyl-N-(2,4-dinitro-phenyl)-hydroxylamine 

Relevant articles and documents

Reactions of bis(2,4-dinitrophenyl) phosphate with hydroxylamine

For dephosphorylation of bis(2,4-dinitrophenyl) phosphate (BDNPP) by hydroxylamine in water, pH region 4-12, the observed first-order rate constant, kobs, initially increases as a function of pH, but is pH-independent between pH 7.2 and pH 10. The initial BDNPP cleavage by nonionic NH 2OH (a short-lived O-phosphorylated hydroxylamine, 2, followed by three possible reactions: (1) reaction of 2 with hydroxylamine, generating 2,4-dinitrophenyl phosphate (DNPP, 3), which subsequently forms DNP; (2) intramolecular displacement of the second DNP group and rapid decomposition of the cyclic intermediate to form phosphonohydroxylamine and eventually inorganic phosphate; (3) a novel rearrangement with intramolecular aromatic nucleophilic substitution involving a cyclic intermediate and migration of the 2,4-dinitrophenyl group from O to N. Values of kobs increase modestly with pH > 10, the reaction is biphasic, and the yield of DNP increases. An increase in [NH2OH] also increases the yield of DNP, due largely to accelerated hydrolysis of DNPP.

Mechanisms of nucleophilic substitution reactions of methylated hydroxylamines with bis(2,4-dinitrophenyl)phosphate. Mass spectrometric identification of key intermediates

Mono- and dimethylation of hydroxylamine on nitrogen does not significantly affect rates of initial attack of NHMeOH and NMe2OH on bis(2,4-dinitrophenyl)phosphate (BDNPP), which is largely by oxygen phosphorylation. O-Methylation, however, blocks this reaction and NH 2OMe then slowly reacts with BDNPP via N-attack at phosphorus and at the aryl group. With NHMeOH, the initial product of O-attack at phosphorus reacts further, either by reaction with a second NHMeOH or by a spontaneous shift of NHMe to the aryl group via a transient cyclic intermediate. There is a minor N-attack of NHMeOH on BDNPP in an SN2(Ar) reaction. Reactions occurring via N-attack are blocked by N-dimethylation, and reaction of NMe 2OH with BDNPP occurs via O-attack, generating a long-lived product. Reaction mechanisms have been probed, and intermediates identified, by using both NMR and MS spectroscopy, with the novel interception of key reaction intermediates in the course of reaction by electrospray ionization mass and tandem mass spectrometry.

SULFONAMIDE DERIVATIVES

The present invention relates to microbicides for agricultural or horticultural use containing sulfonamide derivative of, for example, a formula (I):or a salt thereof,[wherein A1is (1) an aryl group which may be substituted or (2) a heterocyclic group which may be substituted, X1is (1) a chemical bond, (2) a methylene group which may be substituted, or (3) a vinylene group which may be substituted, B1is a five-membered heterocyclic group comprising nitrogen or sulfur atoms as the ring-constructing atoms except for carbon atoms and may be substituted or a condensed heterocyclic group which may be substituted, Z1is (1) a hydrocarbon group which may be substituted, (2) an acyl group which may be substituted, (3) formyl group, (4) an amino group which may be substituted, (5) a group represented by -N=CR1R2(wherein each of R1and R2is a hydrogen atom or a hydrocarbon group which may be substituted), (6) a cyclic amino group, (7) a group represented by -OR3(wherein R3is a hydrogen atom, a hydrocarbon group which may be substituted, an acyl group which may be substituted, formyl group or an alkylsulfonyl group which may be substituted) or (8) -S(O)nR4(wherein n stands for an integer from 0 to 2, R4stands for a hydrogen atom or a hydrocarbon group which may be substituted). The said compounds or the salts thereof are sulfonamide derivatives with microbicidal action, areuseful as excellent microbicides for agricultural or horticultural use, because they are safe, and they have little influence on human beings, farm animals, natural enemies, or the environment, and exert excellent control effects even on resistant microbes.