N-Phenylhydroxylamine - ≥98%(HPLC) , CAS No.100-65-2

CAS: 100-65-2 Cat. No.: N131374 Molecular Weight: 109.13 EC Number: 202-875-6

GRADE & PURITY ≥98%(HPLC)

Synonyms

J-000193 | N-phenyl hydroxylamine | UNII-282MU82Z9A | A800252 | NSC 223099 | AMY18021 | NSC-223099 | beta-Phenylhydroxylamine | Hydroxylamine, N-phenyl- | N-PHENYLHYDROXYLAMINE | N-Phenyl-hydroxylamine | .beta.-Phenylhydroxylamine | N-hydroxylaniline | ph

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Introduction

N-Phenylhydroxylamine is a useful synthetic intermediate. It was used as a reagent to prepare 6-halo-2-amino-3-formylchromones as potential topoisomerase inhibitor anticancer agents. It was also used in the synthesis of N-(chlorophenyl)cycloalkyl-hydroxamic acids and N-phenyl-N-hydroxycyclohexylacetamide with anti-viral activities.

Application

N-Phenylhydroxylamine can be used as a starting material for the synthesis of: 

· 2-alkylindoles by treating with aliphatic terminal alkynes using gold catalyst via sequential 3,3-rearrangements and cyclodehydrations. 

· Isoxazolidines by reacting with aldehydes and α, β-unsaturated aldehydes via a three-component one-pot catalytic reaction. 

· Tetrahydro-1,2-oxazines by treating with an aldehyde and cyclopropane via homo 3+2 dipolar cycloaddition reaction

Specifications

Synonyms

J-000193 | N-phenyl hydroxylamine | UNII-282MU82Z9A | A800252 | NSC 223099 | AMY18021 | NSC-223099 | beta-Phenylhydroxylamine | Hydroxylamine, N-phenyl- | N-PHENYLHYDROXYLAMINE | N-Phenyl-hydroxylamine | .beta.-Phenylhydroxylamine | N-hydroxylaniline | ph

Specifications & Purity

≥98%(HPLC)

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504751377
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751377
• Canonical Smiles: C1=CC=C(C=C1)NO
• IUPAC Name: N-phenylhydroxylamine
• InChIKey: CKRZKMFTZCFYGB-UHFFFAOYSA-N
• INCHI: 1S/C6H7NO/c8-7-6-4-2-1-3-5-6/h1-5,7-8H
• Isomeric SMILES: C1=CC=C(C=C1)NO
• WGK Germany: 3
• RTECS: NC4900000
• UN Number: 2811
• Packing Group: I
• Molecular Weight: 109.13
• Reaxy-Rn: 507174
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=507174&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class N-phenylhydroxylamines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: N-phenylhydroxylamines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: N-phenylhydroxylamines
• Alternative Parents: Arylhydroxamates 1-hydroxylamino, 4-unsubstituted benzenoids 1-hydroxylamino, 2-unsubstituted benzenoids Benzene and substituted derivatives N-organohydroxylamines Organopnictogen compounds Organic oxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: N-phenylhydroxylamine - 1-hydroxylamino, 4-unsubstituted benzenoid - 1-hydroxylamino, 2-unsubstituted benzenoid - Arylhydroxamate - Monocyclic benzene moiety - N-organohydroxylamine - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-phenylhydroxylamines. These are hydroxylamines that are N-substituted with a phenyl group.
• External Descriptors: a small molecule

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Sult1a1 Aryl sulfotransferase (136 Activities)

Discover Target: Sult1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

UL80 Human herpes virus 5 capsid protein P40 (342 Activities)

Discover Target: UL80

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Melt Point(°C): 80-84℃
• Molecular Weight: 109.130 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 109.053 Da
• Monoisotopic Mass: 109.053 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 59.500
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Mengting Chen, Meihua Zhang, Xiaoshuang Liu, Yingxin Liu.  (2023)  Pt/C-catalyzed Selective Hydrogenation of Nitroarenes to N-arylhydroxylamines under Mild Conditions.  ChemistrySelect,  8  (37): (e202301117).  [PMID:] [10.1002/slct.202301117]

2. Shengnan Yue, Xueguang Wang, Shaoting Li, Yao Sheng, Xiujing Zou, Xionggang Lu, Chunlei Zhang.  (2020)  Highly selective hydrogenation of halogenated nitroarenes over Ru/CN nanocomposites by in situ pyrolysis.  NEW JOURNAL OF CHEMISTRY,  44  (27): (11861-11869).  [PMID:] [10.1039/D0NJ02165B]

3. Ying Lü, Jianfa Li, Yimin Li, Liping Liang, Huaping Dong, Kun Chen, Chunxia Yao, Zhanfeng Li, Jinxiang Li, Xiaohong Guan.  (2018)  The roles of pyrite for enhancing reductive removal of nitrobenzene by zero-valent iron.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2018.09.086]

4. Jiahui Xu, Xianlang Chen, Jia-qi Bai, Zhengan Miao, Yuan Tan, Nannan Zhan, Huangfei Liu, Mei Ma, Mengdie Cai, Qin Cheng, Song Sun.  (2024)  Efficient Co/NSPC catalyst for selective hydrogenation of halonitrobenzenes and mechanistic insight.  Catalysis Science & Technology,  14  (5): (1167-1180).  [PMID:] [10.1039/D3CY01767B]

5. Shuchen Wang, Kai He, Yuanfang Lai, Feng He.  (2024)  Enhanced removal of nitrobenzene with lignosulfonate modified zero valent iron: removal kinetic, reaction mechanism, and application feasibility.  Journal of Environmental Chemical Engineering,      [PMID:] [10.1016/j.jece.2024.112023]

6. Guanru Chen, Fengjian Chu, Shuheng Zhang, Wangyu Li, Shiwen Zhou, Wei Wei, Weiwei Chen, Xiaozhi Wang, Lei Yue, Hongru Feng, Yanli Cui, Yuanjiang Pan.  (2024)  Ortho C–H Bond Activations in an Atmospheric Microwave Plasma Ion Source.  JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY,      [PMID:38597607] [10.1021/jasms.4c00011]

7. Jia-qi Bai, Jiahui Xu, Mei Ma, Zhengan Miao, Jiawen Yu, Huangfei Liu, Zhangkai Qian, Mengdie Cai, Qin Cheng, Yong Jiang, Song Sun.  (2024)  Photo-thermal Catalytic Hydrogenation of Halogenated Nitrobenzenes over Ni/P25 Catalyst.  LANGMUIR,      [PMID:38809579] [10.1021/acs.langmuir.4c01132]

8. Jiaxin Li, Ganceng Yang, Yanqing Jiao, Hongyan Sun, Jiaqi Wang, Yue Liu, Chungui Tian, Haijing Yan, Honggang Fu.  (2025)  Charge redistribution of Mo-incorporated Fe2Ni2N customizes potential-determining step for highly selective electroreduction of nitrobenzene to azoxybenzene.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2025.125358]

9. Hong-Da Zhang, Wei-Yao Yang, Miao Pang, Ya-Qiao Tian, Shi-Chao Su, Zhi-Ping Zhao, Le Sang.  (2025)  Hydrophobic Ni foam catalyst for nitrobenzene hydrogenation enhancement in micropacked bed reactors.  AICHE JOURNAL,      [PMID:] [10.1002/aic.18846]