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5-METHOXY-2-NITROANILINE, also known as 5-Methoxy-2-nitrobenzenamine, is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its nitro group and methoxy group attached to the benzene ring, which contribute to its reactivity and potential applications in the pharmaceutical industry.

16133-49-6

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16133-49-6 Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-2-NITROANILINE is used as a synthetic intermediate for the development of methoxybenzimidazole compounds. These compounds act as inhibitors of PI3K, a protein involved in cell growth and survival, and are used in the therapeutic treatment of cancer.
Additionally, 5-METHOXY-2-NITROANILINE is used as a synthetic intermediate for the development of NR2B-selective NMDA receptor antagonists. These antagonists are employed in the treatment of a range of nervous system disorders, such as chronic pain, anxiety, and neurodegenerative diseases, by selectively targeting the NR2B subunit of the NMDA receptor.

Check Digit Verification of cas no

The CAS Registry Mumber 16133-49-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,1,3 and 3 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 16133-49:
(7*1)+(6*6)+(5*1)+(4*3)+(3*3)+(2*4)+(1*9)=86
86 % 10 = 6
So 16133-49-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O3/c1-12-5-2-3-7(9(10)11)6(8)4-5/h2-4H,8H2,1H3

16133-49-6 Well-known Company Product Price

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  • Alfa Aesar

  • (H34046)  5-Methoxy-2-nitroaniline, 98%   

  • 16133-49-6

  • 1g

  • 277.0CNY

  • Detail
  • Alfa Aesar

  • (H34046)  5-Methoxy-2-nitroaniline, 98%   

  • 16133-49-6

  • 10g

  • 1499.0CNY

  • Detail
  • Aldrich

  • (722227)  5-Methoxy-2-nitroaniline  97%

  • 16133-49-6

  • 722227-25G

  • 1,003.86CNY

  • Detail

16133-49-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-Methoxy-2-nitroaniline

1.2 Other means of identification

Product number -
Other names Benzenamine, 5-methoxy-2-nitro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16133-49-6 SDS

16133-49-6Related news

Molecular structure, hydrogen-bonding patterns and topological analysis (QTAIM and NCI) of 5-METHOXY-2-NITROANILINE (cas 16133-49-6) and 5-METHOXY-2-NITROANILINE (cas 16133-49-6) with 2-amino-5-nitropyridine (1:1) co-crystal07/17/2019

In this work, we report an analysis of the molecular structure and the hydrogen-bonding patterns in the crystal structures of 5-methoxy-2-nitroaniline (1) and 5-methoxy-2-nitroaniline with 2-amino-5-nitropyridine (1:1) co-crystal (2). X-ray single crystal diffraction experiments were carried out...detailed

16133-49-6Relevant academic research and scientific papers

Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives

Wu, Daoxin,Liu, Minhua,Li, Zhong,Dang, Mingming,Liu, Xingping,Li, Jianming,Huang, Lu,Ren, Yeguo,Zhang, Zai,Liu, Weidong,Liu, Aiping

, p. 8 - 14 (2019)

A series of novel imidazo[4,5-b]pyridine derivatives were synthesized and their structures were characterized by NMR spectroscopy, mass spectrometry and elemental analysis. The results of bioassays showed that some compounds exhibit good fungicidal activity against Puccinia polysora In particular, compound 7b showed an EC50 value of 4.00 mg/L, which was comparable with that of tebuconazole. Besides, preliminary structure-activity relationship was discussed.

Palladium(II)-catalyzed, heteroatom-directed, regioselective C-H nitration of anilines using pyrimidine as a removable directing group

Pawar, Govind Goroba,Brahmanandan, Abhilashamole,Kapur, Manmohan

, p. 448 - 451 (2016/02/18)

A new palladium-catalyzed, heteroatom-directed strategy for C-H nitration of anilines is described. This C-H functionalization reaction is highly ortho-selective and results in very good yields. The highlight of the work is the use of pyrimidine as the removable directing group. This approach constitutes one of the rare methods of ortho-nitration of anilines, a reaction that is normally very difficult to achieve via traditional approaches.

Conformationally restricted dynamic supramolecular catalysts for substrate-selective epoxidations

Sheibani, Esmaeil,Waernmark, Kenneth

experimental part, p. 2059 - 2067 (2012/04/23)

A second generation of a substrate-selective dynamic supramolecular catalytic system consisting of a catalyst part and a receptor part, connected by a hydrogen-bonding motif, has been realized based on rational design. The results from analyses of the equilibrium mixture of the species generated by the components of the first generation system led us to selectively lock the cisoid conformation of the catalyst part to increase the amount of the substrate-selective catalytic cavity in the equilibrium mixture. This was realized by strapping the catalyst part by organic synthesis. This strapping led to an increase in substrate selectivity in the pair-wise competitive epoxidations of pyridyl- vs. phenyl-appended styrenes and pyridyl- vs. phenyl-appended stilbenes of both Z- and E- configuration compared to the first generation system, reaching 3.4:1 as the highest substrate selectivity for Z-mono-pyridyl-stilbene (27a) vs. the corresponding all-carbon analogue (28a) and for E-dipyridyl-stilbene (26b) vs. the corresponding all-carbon analogue (28b), respectively.

Synthesis of atropisomeric 5,5′-linked biphenyl bisaminophosphine ligands and their applications in asymmetric catalysis

Zhang, Yong Jian,Wei, Hao,Zhang, Wanbin

experimental part, p. 1281 - 1286 (2009/04/18)

Atropisomeric 5,5′-linked biphenyl bisaminophosphine ligands 2 has been synthesized. The axial chirality of this type of ligands can be retained by macro-ring strain produced from 5,5′-linkage of biphenyl even without 6,6′-substituents on biphenyls. The Rh complex of bisaminophosphine 2a as a catalyst is effectively working in the asymmetric hydrogenation of methyl (Z)-2-acetamido-3-arylacrylates, however, for hydrogenation of arylenamide, the low enantioselectivity was observed. When the ligands applied to Pd-catalyzed allylic alkylation, it is found that ligand 2b having a longer backbone linkage is a better ligand for enantioselection in the reaction.

Triazole Derivatives

-

Page/Page column 37, (2009/01/20)

Novel triazole derivatives are inhibitors of TGF-beta receptor I kinase, and can be employed, inter alia, for the treatment of tumours.

Highly chemoselective nitration of aromatic amines using the Ph3P/Br2/AgNO3 system

Iranpoor, Nasser,Firouzabadi, Habib,Nowrouzi, Najmeh,Firouzabadi, Dena

, p. 6879 - 6881 (2007/10/03)

The use of PPh3/Br2/AgNO3 provides a new reagent system for the novel and highly chemoselective nitration of aromatic amines under mild reaction conditions.

Benzotriazine inhibitors of kinases

-

Page/Page column 90, (2008/06/13)

The invention provides benzotriazine compounds having formula (I). The benzotriazine compounds of the invention are capable of inhibiting kinases, such members of the Src kinase family, and various other specific receptor and non-receptor kinases.

Process for preparing isomerically pure prodrugs of proton pump inhibitors

-

Page/Page column 26, (2010/02/10)

Synthetic methods for preparing isomerically pure N-arylsulfonyl derivatives of proton pump inhibitors which include a substituted benzimidazole nucleus are shown by the synthetic schemes and experimental description.

A Combined Experimental and Theoretical Approach toward the Development of Optimized Luminescent Carbostyrils

Strohmeier, Gernot A.,Fabian, Walter M. F.,Uray, Georg

, p. 215 - 226 (2007/10/03)

The synthesis and photophysical data of new carbostyrils (quinoline-2(1H)-ones) with the longest hitherto observed absorption- and emission wavelengths are described. Introduction of 6-amino, 7-MeO, and 4-(CF3) substituents enabled us to rise the absorption and fluorescence maxima up to 414 and 557 nm, respectively. Supported by semi-empirical and ab initio calculations, the 6,7-(1,4-diazine)-fused carbostyril 23b displayed absorption maxima at up to 440 nm, with quantum yields of up to 0.9 and large Stokes shifts (> 100 nm), comparable to the best coumarin chromophores known. The new fluorophore is neither pH-sensitive between pH 6 and 10 nor susceptible to O2 quenching. At pH 3, the emitted light appears greenish-white, which arises from three different stages of protonation.

Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments

-

Page/Page column 24; 47, (2010/02/08)

The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.

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