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

Chemical Properties

Light yellow solid

Uses

Different sources of media describe the Uses of 17508-17-7 differently. You can refer to the following data:
1. Efficient agent for metal-free amination of arylboronic acids leading to primary anilines. Reagents used in Rhodium-catalyzed aziridines formation.
2. O-(2,4-Dinitrophenyl)hydroxylamine is a rapid active-site-directed inhibitor of D-amino acid oxidase; modification results in specific incorporation of an amine group into an accessible nucleophilic r esidue with concomitant release of 2,4-dinitrophenol.

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

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

Downstream Products

• 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 
• 17188-31-7 Pentan-2-one O-(2,4-dinitro-phenyl)-oxime 
• 17188-34-0 Heptan-2-one O-(2,4-dinitro-phenyl)-oxime 
• 17188-39-5 3-Chloro-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 17188-46-4 3-Hydroxy-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 17188-44-2 4-Bromo-benzaldehyde O-(2,4-dinitro-phenyl)-oxime 
• 17188-52-2 (E)-2-Methyl-3-phenyl-propenal O-(2,4-dinitro-phenyl)-oxime 
• 17188-51-1 33-DNO 
• 17301-75-6 (E)-1,3-Diphenyl-propenone O-(2,4-dinitro-phenyl)-oxime 
• 17188-26-0 Cyclopentanone O-(2,4-dinitro-phenyl)-oxime 
• 13181-39-0 (Z)-3-Phenyl-propenal O-(2,4-dinitro-phenyl)-oxime 
• 13181-14-1 1-phenylethan-1-one O-(2,4-dinitrophenyl) 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.

Structure and Reactivity of a High-Spin, Nonheme Iron(III)-Superoxo Complex Supported by Phosphinimide Ligands

Nonheme iron oxygenases utilize dioxygen to accomplish challenging chemical oxidations. A further understanding of the Fe-O2 intermediates implicated in these processes is challenged by their highly transient nature. To that end, we have developed a ligand platform featuring phosphinimide donors intended to stabilize oxidized, high-spin iron complexes. O2 exposure of single crystals of a three-coordinate Fe(II) complex of this framework allowed for in crystallo trapping of a terminally bound Fe-O2 complex suitable for XRD characterization. Spectroscopic and computational studies of this species support a high-spin Fe(III) center antiferromagnetically coupled to a superoxide ligand, similar to that proposed for numerous nonheme iron oxygenases. In addition to the apparent stability of this synthetic Fe-O2 complex, its ability to engage in a range of stoichiometric and catalytic oxidation processes demonstrates that this iron-phosphinimide system is primed for development in modeling oxidizing bioinorganic intermediates and green oxidation chemistry.

Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones

Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.