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1-Benzyl-5-nitro-1H-indazole, a chemical compound with the molecular formula C15H12N4O2, is a benzene derivative characterized by the presence of a nitro group and an indazole ring structure. 1-BENZYL-5-NITRO-1H-INDAZOLE, known for its unique structural and chemical properties, holds potential for a variety of applications across different industries, including organic synthesis, pharmaceuticals, and agrochemicals. Its versatility as a building block in the production of various chemicals and as an intermediate in the synthesis of pharmaceutical drugs makes it a compound of significant interest for further research and development.

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  • 23856-20-4 Structure
  • Basic information

    1. Product Name: 1-BENZYL-5-NITRO-1H-INDAZOLE
    2. Synonyms: 1-BENZYL-5-NITRO-1H-INDAZOLE;1-BENZYL-5-NITRO-1H-INDAZOLE, 95+%;1-benzyl-5-nitroindazole
    3. CAS NO:23856-20-4
    4. Molecular Formula: C14H11N3O2
    5. Molecular Weight: 253.26
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 23856-20-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 451.084°C at 760 mmHg
    3. Flash Point: 226.608°C
    4. Appearance: /
    5. Density: 1.31g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.668
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-BENZYL-5-NITRO-1H-INDAZOLE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-BENZYL-5-NITRO-1H-INDAZOLE(23856-20-4)
    12. EPA Substance Registry System: 1-BENZYL-5-NITRO-1H-INDAZOLE(23856-20-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 23856-20-4(Hazardous Substances Data)

23856-20-4 Usage

Uses

Used in Organic Synthesis:
1-Benzyl-5-nitro-1H-indazole is used as a building block in organic synthesis for the creation of a range of chemical compounds. Its unique structure allows for the formation of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
1-Benzyl-5-nitro-1H-indazole is utilized as an intermediate in the synthesis of pharmaceutical drugs. Its chemical properties make it a valuable component in the development of new medications, potentially contributing to advancements in healthcare.
Used in Agrochemicals:
In the agrochemical industry, 1-Benzyl-5-nitro-1H-indazole may be employed in the development of new pesticides or other agricultural chemicals. Its potential role in this sector underscores its broad applicability in chemical innovation.
Each of these uses highlights the compound's adaptability and the importance of continued research into its properties and potential applications. As the scientific community explores new ways to harness the capabilities of 1-benzyl-5-nitro-1H-indazole, its role in various industries is likely to expand, offering innovative solutions to existing challenges.

Check Digit Verification of cas no

The CAS Registry Mumber 23856-20-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,8,5 and 6 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 23856-20:
(7*2)+(6*3)+(5*8)+(4*5)+(3*6)+(2*2)+(1*0)=114
114 % 10 = 4
So 23856-20-4 is a valid CAS Registry Number.
InChI:InChI=1/C14H11N3O2/c18-17(19)13-6-7-14-12(8-13)9-15-16(14)10-11-4-2-1-3-5-11/h1-9H,10H2

23856-20-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-benzyl-5-nitroindazole

1.2 Other means of identification

Product number -
Other names 5-nitro-1-(phenylmethyl)-1H-indazole

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:23856-20-4 SDS

23856-20-4Relevant articles and documents

Targeting Her2-insYVMA with Covalent Inhibitors - A Focused Compound Screening and Structure-Based Design Approach

Lategahn, Jonas,Hardick, Julia,Grabe, Tobias,Niggenaber, Janina,Jeyakumar, Kirujan,Keul, Marina,Tumbrink, Hannah L.,Becker, Christian,Hodson, Luke,Kirschner, Tonia,Kl?vekorn, Philip,Ketzer, Julia,Baumann, Matthias,Terheyden, Susanne,Unger, Anke,Weisner, J?rn,Müller, Matthias P.,Van Otterlo, Willem A. L.,Bauer, Sebastian,Rauh, Daniel

, p. 11725 - 11755 (2020/11/26)

Mutated or amplified Her2 serves as a driver of non-small cell lung cancer or mediates resistance toward the inhibition of its family member epidermal growth factor receptor with small-molecule inhibitors. To date, small-molecule inhibitors targeting Her2 which can be used in clinical routine are lacking, and therefore, the development of novel inhibitors was undertaken. In this study, the well-established pyrrolopyrimidine scaffold was modified with structural motifs identified from a screening campaign with more than 1600 compounds, which were applied against wild-type Her2 and its mutant variant Her2-A775_G776insYVMA. The resulting inhibitors were designed to covalently target a reactive cysteine in the binding site of Her2 and were further optimized by means of structure-based drug design utilizing a set of obtained complex crystal structures. In addition, the analysis of binding kinetics and absorption, distribution, metabolism, and excretion parameters as well as mass spectrometry experiments and western blot analysis substantiated our approach.

Surmounting the resistance against EGFR inhibitors through the development of thieno[2,3-d]pyrimidine-based dual EGFR/HER2 inhibitors

Milik, Sandra N.,Abdel-Aziz, Amal Kamal,Lasheen, Deena S.,Serya, Rabah A.T.,Minucci, Saverio,Abouzid, Khaled A.M.

supporting information, p. 316 - 336 (2018/06/14)

In light of the emergence of resistance against the currently available EGFR inhibitors, our study focuses on tackling this problem through the development of dual EGFR/HER2 inhibitors with improved enzymatic affinities. Guided by the binding mode of the

Bicyclic heteroaromatic compounds as protein tyrosine kinase inhibitors

-

Page/Page column 39, (2015/12/18)

A pharmaceutical formulation comprising the compound of formula

NOVEL AMINE DERIVATIVE OR SALT THEREOF

-

Paragraph 0452-0453; 0575-0576, (2015/11/11)

A novel amine derivative expressed by general formula (1) (in the formula: G1, G2, and G3 are the same or different and represent CH or a nitrogen atom; R1 represents a chlorine atom, an optionally-substituted C3-8 cycloalkyl group, or the like; R2 represents -COOR5 (in the formula, R5 represents a hydrogen atom or a carboxyl protective group), or the like; R3 represents a hydrogen atom, or the like; and R4 represents an optionally-substituted condensed bicyclic hydrocarbon group, an optionally-substituted bicyclic heterocyclic group, or the like), or a salt thereof is useful in procedures such as the treatment or prevention of conditions related to excessive keratinocyte proliferation.

A method for the regioselective synthesis of 1-alkyl-1H-indazoles

Liu, Han-Jun,Hung, Shiang-Fu,Chen, Chuan-Lin,Lin, Mei-Huey

, p. 3907 - 3912 (2013/06/27)

A method for the regioselective synthesis of 3-unsubstituted 1-alkyl-1H-indazoles, starting with 2-halobenzonitriles and N-alkylhydrazines, is described. The two-step reaction pathway proceeds through the intermediacy of 1-alkyl-3-amino-1H-indazoles follo

Synthesis and cytotoxic activity of 2,5-disubstituted pyrimido[5,4-c] quinoline derivatives

Zhang, Fan,Zhai, Xin,Chen, Li Juan,Qi, Jian Guo,Cui, Bo,Gu, Yu Cheng,Gong, Ping

scheme or table, p. 1277 - 1280 (2012/01/06)

A series of 2,5-disubstituted pyrimido[5,4-c]quinoline derivatives were synthesized and their cytotoxic activity against H460, HT-29 and MDA-MB-231 cell lines was evaluated in vitro. It was found that most of the tested compounds especially compound 17, s

A general, one-step synthesis of substituted indazoles using a flow reactor

Wheeler, Rob C.,Baxter, Emma,Campbell, Ian B.,MacDonald, Simon J. F.

experimental part, p. 565 - 569 (2011/12/02)

Flow chemistry is a rapidly emerging technology within the pharmaceutical industry, both within medicinal and development chemistry groups. The advantages of flow chemistry, increased safety, improved reproducibility, enhanced scalability, are readily apparent, and we aimed to exploit this technology in order to provide small amounts of pharmaceutically interesting fragments via a safe and scalable route, which would enable the rapid synthesis of multigram quantities on demand. Here we report a general and versatile route which utilises flow chemistry to deliver a range of known and novel indazoles, including 3-amino and 3-hydroxy analogues.

Synthesis and evaluation of aniline headgroups for alkynyl thienopyrimidine dual EGFR/ErbB-2 kinase inhibitors

Waterson, Alex G.,Petrov, Kimberly G.,Hornberger, Keith R.,Hubbard, Robert D.,Sammond, Douglas M.,Smith, Stephon C.,Dickson, Hamilton D.,Caferro, Thomas R.,Hinkle, Kevin W.,Stevens, Kirk L.,Dickerson, Scott H.,Rusnak, David W.,Spehar, Glenn M.,Wood, Edgar R.,Griffin, Robert J.,Uehling, David E.

scheme or table, p. 1332 - 1336 (2009/11/30)

Aniline 'headgroups' were synthesized and incorporated into an alkynyl thienopyrimidine series of EGFR and ErbB-2 inhibitors. Potent inhibition of enzyme activity and cellular proliferation was observed. In certain instances, protein binding was reduced a

SUBSTITUTED TETRAHYDROBENZOTHIENOPYRIMIDINAMINE COMPOUNDS USEFUL FOR TREATING HYPER-PROLIFERATIVE DISORDERS

-

Page/Page column 117-118, (2010/02/10)

The present invention relates to a compound of Formula (I) and its use in treating hyper-proliferative disorders.

Optimization of 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitriles as orally active, irreversible inhibitors of human epidermal growth factor receptor-2 kinase activity

Tsou, Hwei-Ru,Overbeek-Klumpers, Elsebe G.,Hallett, William A.,Reich, Marvin F.,Floyd, M. Brawner,Johnson, Bernard D.,Michalak, Ronald S.,Nilakantan, Ramaswamy,Discafani, Carolyn,Golas, Jonathan,Rabindran, Sridhar K.,Shen, Ru,Shi, Xiaoqing,Wang, Yu-Fen,Upeslacis, Janis,Wissner, Allan

, p. 1107 - 1131 (2007/10/03)

A series of new 6,7-disubstituted-4-(arylamino)quinoline-3-carbonitrile derivatives that function as irreversible inhibitors of human epidermal growth factor receptor-2 (HER-2) and epidermal growth factor receptor (EGFR) kinases have been prepared. These compounds demonstrated enhanced activities for inhibiting HER-2 kinase and the growth of HER-2 positive cells compared to our EGFR kinase inhibitor 86 (EKB-569). Three synthetic routes were used to prepare these compounds. They were prepared mostly by acylation of 6-amino-4-(arylamino) quinoline-3-carbonitriles with unsaturated acid chlorides or by amination of 4-chloro-6-(crotonamido)-quinoline-3-carbonitriles with monocyclic or bicyclic anilines. The third route was developed to prepare a key intermediate, 6-acetamido-4-chloroquinoline-3-carbonitrile, that involved a safer cyclization step. We show that attaching a large lipophilic group at the para position of the 4-(arylamino) ring results in improved potency for inhibiting HER-2 kinase. We also show the importance of a basic dialkylamino group at the end of the Michael acceptor for activity, due to intramolecular catalysis of the Michael addition. This, along with improved water solubility, resulted in compounds with enhanced biological properties. We present molecular modeling results consistent with the proposed mechanism of inhibition. Binding studies of one compound, 25o (C-14 radiolabeled), showed that it binds irreversibly to HER-2 protein in BT474 cells. Furthermore, it demonstrated excellent oral activity, especially in HER-2 overexpressing xenografts. Compound 25o (HKI-272) was selected for further studies and is currently in phase I clinical trials for the treatment of cancer.

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