103427-15-2

Basic information

• Product Name: 4-Nitrophenol-15N
• Synonyms: 4-Nitrophenol-15N;1-Hydroxy-4-nitrobenzene-15N;4-Hydroxy-1-nitrobenzene-15N;4-Hydroxynitrobenzene-15N;Niphen-15N;NSC 1317-15N;p-Hydroxynitrobenzene-15N;p-Nitrophenol-15N
• CAS NO: 103427-15-2
• Molecular Formula: C₆H₅NO₃
• Molecular Weight: 140
• Product Categories: Aromatics;Isotope Labelled Compounds
• Mol File: 103427-15-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Nitrophenol-15N(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitrophenol-15N(103427-15-2)
• EPA Substance Registry System: 4-Nitrophenol-15N(103427-15-2)

Safety Data

• Hazardous Substances Data: 103427-15-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitrophenol-15N is used as a labeled compound for the synthesis and development of pharmaceuticals. Its application reason is to facilitate the study of drug metabolism, pharmacokinetics, and pharmacodynamics by providing a distinct isotopic signature that can be easily tracked and distinguished from non-labeled compounds.
Used in Agriculture:
In the agricultural industry, 4-Nitrophenol-15N is used as a labeled compound for the development of fungicides. The application reason is to study the effectiveness of these fungicides against various fungal pathogens and to understand their mode of action, which can lead to the development of more effective and targeted antifungal agents.
Used in Dye Industry:
4-Nitrophenol-15N is also used as a labeled compound in the manufacturing of dyes. The application reason is to enable the investigation of dye interactions with various substrates, such as fabrics and plastics, and to optimize the dyeing process for improved colorfastness and performance. Additionally, the labeled compound can be used to study the environmental impact and degradation pathways of dyes, contributing to the development of more sustainable and eco-friendly products.

Upstream product

• 6407-12-1 <15N>-p-nitrofluorobenzene 
• 108-95-2 phenol 
• 1093389-02-6 sodium 2-[(tert-butyldiphenylsilyl)[⁽¹⁸⁾O]oxy]propyl [⁽¹⁴⁾N]-p-nitrophenyl phosphate 

Downstream Products

• 1131544-85-8 ⁽¹⁸⁾O₂ nonbridge,⁽¹⁵⁾N-p-nitrophenyl methylphosphonate sodium 

Relevant articles and documents

The Mechanism of Nitration by 4-Methyl-4-nitro-2,3,5,6-tetrabromocyclohexa-2,5-dienone

Nitration of phenol by 4-methyl-4-nitro-2,3,5,6-tetrabromocyclohexa-2,5-dienone in diethyl ether is a radical process involving reaction between the phenoxyl radical and NO2 radical that has escaped from a radical pair in which it was formed by homolytic

Concerted or stepwise mechanisms for acyl transfer reactions of p-nitrophenyl acetate? Transition state structures from isotope effects

Isotope effects have been measured for the acyl transfer reactions of p-nitrophenyl acetate (PNPA) with the oxyanion nucleophiles hydroxide, phenolate, and the anion of hexafluoroisopropyl alcohol; with the sulfur anions of mercaptoethanol and methyl 3-me

15N-CIDNP during Photonitration of Phenol with Tetranitromethane and Reactions with Nitric and Nitrous Acid

During the irradiation of phenol (1) with 15N-enriched tetranitromethane in acetonitrile, and during the reaction of 1 with 15N-enriched nitric acid and nitrous acid, emission due to the nitration products o- and p-nitrophenol (2a, 2b) is observed in the 15N-NMR spectra. The CIDNP effects are built up by radical pairs formed by the encounters of the radicals NO2? and 1+? or PhO?. During the reaction of 1 with nitrous acid, 2b is formed, in part due to a non-radical reaction, via oxidation of p-nitrosophenol (3).

Altered transition state for the reaction of an RNA model catalyzed by adinuclear zinc(II) catalyst

The cyclization of 2-(hydroxypropyl)-4-nitrophenyl phosphate (HpPNP) catalyzed by the dinuclear zinc complex of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2- hydroxypropane (1) proceeds by a transition state that is different from that of the uncatalyzed reaction. Kinetic isotope effects (KIEs) measured in the nucleophilic atom and in the leaving group show that theuncatalyzed cyclization has a transition state (TS) with little phospho rus-oxygen bond fission to the leaving group 18klg= 1.0064 ± 0.0009 and 15k = 1.0002 ± 0.0002) a nd that nucleophilic bond formation occurs in the rate-determining step (18knuc ) 1.0326 ( 0.0008). In the catalyzed reaction, larger leaving group isotope effects ( 18klg ) 1.0113 ± 0.0005 and 15k = 1.0015 ± 0.0005) and a smaller nucleophile isotope effect (18k nuc = 1.0116 ± 0.0010) indicate a later TS with greater leaving group bond fission and greater nucleophilic bond formation. These observed nucleophile KIEs are the combined effect of the equilibrium effect on deprotonation of the 2′-hydroxyl nucleophile and the KIE on the nucleophilic step. An EIE of 1.0245 for deprotonation of the hydroxyl group of HPpNP was obtained computationally. The different KIEs for the two reactions indicate that the effective catalysis by 1 is accompanied by selection for an altered transition state, presumably arising from the preferential stabilization by the catalyst of charge away from the nucleophile and toward the leaving group. These results demonstrate the potential fora catalyst using biologically relevant metal ions to select for an alte red transition state for phosphoryl transfer.

15N NUCLEAR POLARISATION IN NITRATION AND RELATED REACTIONS. PART 2. p-NITROPHENOL

The nitrous acid-catalysed nitration of p-nitrophenol by H(15)NO3 in aqueous trifluoroacetic acid gives a strong emission signal during reaction for the 2-(15)NO2 group in the 15N n.m.r. spectrum of the 2,4-dinitrophenol formed: the enhancement is by a factor of up to 600.The reaction is accompanied by 11percent migration of the original 4-nitro group to the 2-position and substitution by the labelled nitro group at the 4-position.The 15N n.m.r. spectrum during the related reaction using 15N labelled p-nitrophenol and unlabelled nitric acid shows that the migration of the 4-(15)NO2 group to the 2-position causes a strongly enhanced absorption signal for the 2-(15)NO2 group in the 2,4-dinitrophenol formed.A strongly enhanced absorption signal for this group is also found for the reaction of p-nitrophenol with H(15)NO3 in the presence of sodium azide.The complete set of results is interpreted in terms of nuclear polarisation deriving from the reactions of the radical pair ArO.NO2. when formed either by diffusion or from a singlet precursor.The reaction between hydrazoic acid and nitric acid is catalysed by p-nitrophenol.