17508-17-7

Basic information

• Product Name: O-(2,4-dinitrophenyl)hydroxylamine
• Synonyms: O-(2,4-dinitrophenyl)hydroxylamine;2,4-Dinitrophenylhydroxylamine;1-aMinooxy-2,4-dinitro-benzene;2,4-DinitrophenoxyaMine;2,4-NitrophenoxyaMine;NSC 148499;HydroxylaMine,O-(2,4-dinitrophenyl)-
• CAS NO: 17508-17-7
• Molecular Formula: C₆H₅N₃O₅
• Molecular Weight: 199.121
• EINECS: 241-512-6
• Product Categories: Amines;Aromatics;Inhibitors;nitro-compound
• Mol File: 17508-17-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 112.5°C
• Boiling Point: 336.62°C (rough estimate)
• Flash Point: 187.9°C
• Appearance: /
• Density: 1.6937 (rough estimate)
• Vapor Pressure: 3.37E-06mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.07±0.70(Predicted)
• CAS DataBase Reference: O-(2,4-dinitrophenyl)hydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: O-(2,4-dinitrophenyl)hydroxylamine(17508-17-7)
• EPA Substance Registry System: O-(2,4-dinitrophenyl)hydroxylamine(17508-17-7)

Safety Data

• Statements: 22-36/37/38
• Safety Statements: 26
• TSCA: No
• Hazardous Substances Data: 17508-17-7(Hazardous Substances Data)

Usage

Description

O-(2,4-dinitrophenyl)hydroxylamine is a light yellow solid that serves as a versatile reagent in various chemical and biological applications due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
O-(2,4-dinitrophenyl)hydroxylamine is used as an efficient agent for metal-free amination of arylboronic acids, leading to the formation of primary anilines. This application is particularly useful in the synthesis of various organic compounds and pharmaceuticals, as it provides a more environmentally friendly and cost-effective alternative to traditional metal-catalyzed amination methods.
Used in Catalyst Preparation:
O-(2,4-dinitrophenyl)hydroxylamine is also used as a reagent in the preparation of rhodium-catalyzed aziridines. Aziridines are important intermediates in the synthesis of various pharmaceuticals and agrochemicals, making this application crucial for the development of new and improved products in these industries.
Used in Enzyme Inhibition:
In the field of biochemistry, O-(2,4-dinitrophenyl)hydroxylamine is used as a rapid active-site-directed inhibitor of D-amino acid oxidase. This inhibition results in the specific incorporation of an amine group into an accessible nucleophilic residue, with the concomitant release of 2,4-dinitrophenol. This property makes it a valuable tool for studying enzyme mechanisms and developing new therapeutic strategies targeting D-amino acid oxidase.
Used in Pharmaceutical Research:
O-(2,4-dinitrophenyl)hydroxylamine's unique chemical properties also make it a promising candidate for pharmaceutical research. Its ability to inhibit D-amino acid oxidase and its use in the synthesis of various organic compounds can lead to the development of new drugs and therapies for a range of medical conditions.

Preparation

To a stirred solution of 13.3 gm (0.1 mole) of t-butyl JV-hydroxycar-bamate and 5.6 gm (0.1 mole) of potassium hydroxide in 200 ml of absolute ethanol is added 20.2 gm (0.1 mole) of 2,4-dinitrochlorobenzene. The resultant deep red solution is stirred at room temperature for 1 hr; then enough glacial acetic acid is added dropwise to produce a light yellow solution. The solution is poured into 1.5 liters of cold water. The yellow oil which separates is gradually converted to crystals. The solid ?-butyl JV-(2,4-dinitrophenoxy)carbamate is separated, dried, and recrystallized from an ethyl acetate-hexane mixture to afford 16.4 gm (53%), m.p. 74-75°C. To 15 ml of trifluoroacetic acid is added 4 gm (0.0133 mole) of the i-butyl J/V-(2,4-dinitrophenoxy)carbamate. After the evolution of carbon dioxide has subsided, the solution is poured into 100 ml of ice water. The resultant oily layer crystallizes on standing to afford 2.5 gm (95%), m.p. 112°C (from ethanol). Recently it was discovered that the alkylation of ethyl JV-hydroxy-carbamate under alkaline conditions, particularly in a DMF medium at 60°C in the presence of sodium bicarbonate, leads to the ultimate formation of O-alkylated hydroxylamines. On the other hand, at 80-85°C, the direct alkylation without the presence of a base ultimately leads to N-alkylhydrox-ylamines (see Table I) [59]. The reaction of ethylazidoformate with an alcohol, while perhaps haz-ardous, may have some merit (Eqs. 31-33). The overall yield, based on ethyl chloroformate, is said to be on the order of 60%.

InChI:InChI=1/C6H5N3O5/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H,7H2

Upstream product

• 17508-16-6 tert-butyl (2,4-dinitrophenoxy)carbamate 
• 54322-32-6 ethyl O-(2,4-dinitrophenyl)acetohydroxamate 
• 54322-32-6 ethyl N-(2,4-dinitrophenoxy)acetimidate 
• 176504-71-5 N-trimethylsilyl-O-2,4-dinitrophenylhydroxylamine 
• 60506-35-6 2-(2,4-dinitrophenoxy)-1H-isoindole-1,3(2H)-dione 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 584-48-5 2,4-dinitrobromobenzene 
• 7803-57-8 hydrazine hydrate 
• 51-28-5 2,4-Dinitrophenol 

Downstream Products

• 13181-41-4 O-(2,4-dinitrophenyl)acetaldoxime 
• 13059-86-4 2,4-dinitro-N-butylaniline 
• 42824-47-5 butylammonium salt of 2,4-dinitrophenol 
• 51-28-5 2,4-Dinitrophenol 
• 26177-38-8 1-bityl-3-methyldiaziridine 
• 64584-77-6 (5S,8R,9R,10S,13S,14S,17S)-17-Hydroxy-13-methyl-hexadecahydro-cyclopenta[a]phenanthren-3-one O-(2,4-dinitro-phenyl)-oxime 
• 13181-75-4 O-(2,4-dinitrophenyl) cyclohexanone oxime 
• 17188-50-0 4-Methyl-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 13181-85-6 4-Chloro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 13356-86-0 2-Chloro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 17188-62-4 51-DNO 
• 13356-88-2 3-Nitro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 13181-38-9 4-Nitro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 

Relevant articles and documents

Formation and reactions of N7-aminoguanosine and derivatives

Arylamines are mutagens and carcinogens and are thought to initiate tumors by forming adducts with DNA. The major adducts are C8-guanyl, and we have previously suggested a role for guanyl-N7 intermediates in the formation process. N7-Aminoguanosine (Guo) was synthesized and characterized, with the position of the NH2 at N7 established by two- dimensional rotating frame Overhauser enhancement NMR spectroscopy. In DMF, N7-NH2Guo formed C8-NH2Guo and the cyclic product C8:5'-O-cycloGuo. In aqueous media, these products were formed along with 8-oxo-7,8-dihydroGuo, N7-NH2guanine, and a product characterized as a purine 8,9-ring-opened derivative (N-aminoformamidopyrimidine). The rate of aqueous decomposition of N7-NH2Guo increased with pH, with a t( 1/2 ) of 10 h at pH 7 and a t( 1/2 ) of 2 h at pH 9. The rate of migration of NH2 from N7 to C8 is fast enough to explain the formation of C8-NH2Guo from the reaction of 2,4- dinitrophenoxyamine with Guo but not the formation of C8-(arylamino)Guo in the reaction of Guo with aryl hydroxylamine esters; however, the fluorenyl moiety may facilitate the proposed rearrangement by stabilizing an incipient negative charge in the transfer. In the reaction of Guo with N-hydroxy-2- aminofluorene and acetylsalicylic acid, a peak with the mass spectrum expected for N7-(2-aminofluorenyl)Guo was detected early in the reaction and was distinguished from C8-(2-aminofluorenyl)Guo. NMR experiments with [8- 13C]Guo also provided some additional support for transient formation of N7-(2-aminofluorenyl)Guo. We conclude that a guanyl-N7 intermediate is reasonable in the reaction of activated arylamines with nucleic acids, although an exact rate of transfer of an N7-arylamine group to the C8 position has not yet been quantified. The results provide an explanation for the numerous products associated with modification of DNA by activated arylamines. However, the contribution of 'direct' reaction at the guanine C8 atom cannot be excluded.

2,2,2-Trifluoroacetaldehyde O-(Aryl)oxime: A Precursor of Trifluoroacetonitrile

The preparation of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime, a previously inaccessible precursor of trifluoroacetonitrile, via reaction of hydroxylamine and trifluoroacetaldehyde hydrate is reported. This precursor released CF3CN in quantitative yield under mildly basic conditions. The precursor was successfully used in the synthesis of trifluoromethylated oxadiazoles. The facile, cost-effective, scalable, and recyclable procedure makes these trifluoroacetonitrile precursors generally applicable.

Synthesis method of 2,4 -nitrobenzoic acid amine and reaction vessel

The technical scheme is that the 2, 4 -dinitrobenzene oxyamine synthesis method comprises a box body, a reaction kettle arranged in the box body, a clamping assembly used for clamping the reaction kettle, and a moving assembly which drives the reaction kettle to move. A partition plate and vertically inserted into the box body covers the cover plate at the top end of the box body. The number of the separation plates is a plurality of partition plates, the box body is divided into a plurality of different chambers, and the cavity chambers are divided into discharge chambers arranged at the two ends and a heat preservation chamber arranged in the middle. The cover plate is arranged at the top end of the heat preservation chamber, and a heat preservation plate is arranged in the heat preservation chamber. This application has the effect of convenient regulation and control to the temperature of reaction.

Visible Light as a Sole Requirement for Intramolecular C(sp3)-H Imination

A novel, simple, and practical visible-light-mediated intramolecular α-C(sp3)-H imination of tertiary aliphatic amines containing β-O-aryl oximes leading to N-heterocycles has been developed. The reaction was performed well at rt with tolerance of some functional groups. Importantly, the selective C-H functionalization did not require added catalyst, oxidant, additive, acid, and base; visible light was the sole requirement.