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N1-(2,4-Dichlorophenyl)benzamide, a chemical compound with the molecular formula C13H9Cl2NO, is a benzamide derivative characterized by the presence of two chlorine atoms attached to a phenyl ring. N1-(2,4-DICHLOROPHENYL)BENZAMIDE holds potential in the pharmaceutical and organic synthesis industries, serving as a building block for the creation of biologically active molecules and pharmaceutical drugs. Its unique structure and properties make it a subject of interest for further research into its possible pharmacological activities.

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  • 10286-76-7 Structure
  • Basic information

    1. Product Name: N1-(2,4-DICHLOROPHENYL)BENZAMIDE
    2. Synonyms: N1-(2,4-DICHLOROPHENYL)BENZAMIDE;N-(2,4-DICHLOROPHENYL)BENZAMIDE
    3. CAS NO:10286-76-7
    4. Molecular Formula: C13H9Cl2NO
    5. Molecular Weight: 266.12
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 10286-76-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 300.4°Cat760mmHg
    3. Flash Point: 135.5°C
    4. Appearance: /
    5. Density: 1.384g/cm3
    6. Vapor Pressure: 0.00112mmHg at 25°C
    7. Refractive Index: 1.656
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: N1-(2,4-DICHLOROPHENYL)BENZAMIDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: N1-(2,4-DICHLOROPHENYL)BENZAMIDE(10286-76-7)
    12. EPA Substance Registry System: N1-(2,4-DICHLOROPHENYL)BENZAMIDE(10286-76-7)
  • Safety Data

    1. Hazard Codes:  Xn:Harmful;
    2. Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
    3. Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 10286-76-7(Hazardous Substances Data)

10286-76-7 Usage

Uses

Used in Pharmaceutical Industry:
N1-(2,4-Dichlorophenyl)benzamide is used as a building block for the synthesis of various biologically active molecules and pharmaceutical drugs. Its unique structure allows for the development of new compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, N1-(2,4-Dichlorophenyl)benzamide serves as a key intermediate for the production of a range of chemical compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of various organic compounds.
Used in Research and Development:
N1-(2,4-Dichlorophenyl)benzamide is used as a subject of research for its potential pharmacological activities. Its biological effects and interactions with biological systems are of interest to scientists, who aim to explore its possible applications in medicine and drug development.

Check Digit Verification of cas no

The CAS Registry Mumber 10286-76-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,2,8 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 10286-76:
(7*1)+(6*0)+(5*2)+(4*8)+(3*6)+(2*7)+(1*6)=87
87 % 10 = 7
So 10286-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H9Cl2NO/c14-10-6-7-12(11(15)8-10)16-13(17)9-4-2-1-3-5-9/h1-8H,(H,16,17)

10286-76-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(2,4-dichlorophenyl)benzamide

1.2 Other means of identification

Product number -
Other names benzoic acid-(2,4-dichloro-anilide)

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:10286-76-7 SDS

10286-76-7Relevant articles and documents

Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: The isocyano group as an N1 synthon

Liu, Jian-Quan,Shen, Xuanyu,Liu, Zhenhua,Wang, Xiang-Shan

, p. 6314 - 6317 (2017)

An interesting radical coupling reaction of aromatic aldehydes with isocyanides was disclosed for the synthesis of amides catalyzed by copper. According to the experimental results and mechanistic study, the isocyano group acted as an N1 synthon rather than exhibiting the carbene-like reactivity, exploiting a new reactivity profile of isocyanides.

N-Acyltetrazole as an intermediate for preparation of carboxylic acid derivatives

Jursic

, p. 361 - 364 (1993)

A new mild and very efficient procedure for preparation of acid derivatives via N-acyl-5-phenyltetrazole is reported. The yields are high at -10°C and purification is simple but, because of the thermal instability of the intermediate, a certain amount of corresponding oxadiazole arises if the reaction is carried out at higher temperature.

Efficient Electrocatalysis for the Preparation of (Hetero)aryl Chlorides and Vinyl Chloride with 1,2-Dichloroethane

Liang, Yujie,Lin, Fengguirong,Adeli, Yeerlan,Jin, Rui,Jiao, Ning

supporting information, p. 4566 - 4570 (2019/02/14)

Although the application of 1,2-dichloroethane (DCE) as a chlorinating reagent in organic synthesis with the concomitant release of vinyl chloride as a useful byproduct is a fantastic idea, it still presents a tremendous challenge and has not yet been achieved because of the harsh dehydrochlorination conditions and the sluggish C?H chlorination process. Here we report a bifunctional electrocatalysis strategy for the catalytic dehydrochlorination of DCE at the cathode simultaneously with anodic oxidative aromatic chlorination using the released HCl as the chloride source for the efficient synthesis of value-added (hetero)aryl chlorides. The mildness and practicality of the protocol was further demonstrated by the efficient late-stage chlorination of bioactive molecules.

Revisiting 1-chloro-1,2-benziodoxol-3-one: Efficient: ortho -chlorination of aryls under aqueous conditions

Vinayak, Botla,Ravindrakumar, Pardhi Vishal,Ramana, Daggupati V.,Chandrasekharam, Malapaka

, p. 8953 - 8959 (2018/06/08)

The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho-selective chlorination proceeds in the absence of a radical initiator. Various electronically differentiated anilides and sulfonamides are tolerated under aqueous conditions.

Amide-assisted radical strategy: Metal-free direct fluorination of arenes in aqueous media

Liang, Deqiang,Li, Yanni,Gao, Shulin,Li, Renlun,Li, Xiangguang,Wang, Baoling,Yang, Hai

supporting information, p. 3344 - 3349 (2017/07/28)

A metal- and initiator-free direct fluorination of arenes with the assistance of an amide group is developed. This reaction proceeded under simple aqueous conditions with good functional group tolerance and ortho-para selectivity, and is highly practical because it could be readily scaled up to a multigram-scale. At this stage, an exclusive mechanism could not be proposed, and several possibilities have been discussed. The possibility of the amide-assisted radical chain mechanism has been supported by experimental and computational investigations as well as a seminal work.

Molecular modeling studies, synthesis and biological evaluation of derivatives of N-phenylbenzamide as Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors

Desai, Kumar R.,Shaikh, Mushtaque S.,Coutinho, Evans C.

experimental part, p. 321 - 332 (2012/06/01)

The search for new antimalarial agents is necessary as current drugs in the market have become vulnerable due to the emergence of resistant strains of Plasmodium falciparum (Pf). The enzyme dihydroorotate dehydrogenase (PfDHODH) is a validated target for development of antimalarial agents. PfDHODH is a crucial enzyme in the de novo pyrimidine biosynthesis pathway and is essential for the growth of the parasite. In this article, we report the design, synthesis and evaluation of benzanilides as inhibitors of PfDHODH. From the pool of molecules designed using molecular modeling techniques, candidates were shortlisted for further evaluation based on docking scores and 3D-QSAR studies. The activities of these shortlisted analogs were predicted from CoMFA and CoMSIA models. The most promising molecules were synthesized using solvent-free microwave-assisted synthesis and their structures characterized by spectroscopic techniques. The molecules were screened for in vitro antimalarial activity by the whole cell assay method. Two molecules viz. KMC-3 and KMC-15 were found to be active at 8.7 and 5.7 μM concentrations, respectively. Springer Science+Business Media, LLC 2011.

Aminolysis of allyl esters with bislithium aryl amides

Faler, Catherine A.,Joullié, Madeleine M.

, p. 7229 - 7231 (2007/10/03)

The aminolysis of allyl esters with bislithium amides is reported. Tertiary aryl amides were synthesized in a one-pot reaction with bislithium amides and a suitable electrophile in good yields. The scope of this reaction was demonstrated with a variety of anilines and aminopyridines and applied to the synthesis of triphenylmethylacetamides.

Activation of the aryl hydrocarbon receptor by methyl yellow and related congeners: structure-activity relationships in halogenated derivatives.

Kato, Taka-aki,Matsuda, Tomonari,Matsui, Saburo,Mizutani, Takaharu,Saeki, Ken-ichi

, p. 466 - 471 (2007/10/03)

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure-activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2'- and 6'-position), and reduction by substitution at the para-position (4'-position). The greatest enhancement of the ligand activity was observed in 2',6'-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4'-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2')-chlorine-substitution, and the AhR ligand activity of 2',4'-dichlorobenzanilide was similar to that of 2'-chloro-MY. These results suggest that the amide bond is equivalent to the -N=N- or -CH=CH- double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.

AlCl3-mediated migration of benzamido group of N-phenoxybenzamide derivatives to the phenyl group

Miyazawa, Etsuko,Sakamoto, Takeshi,Kikugawa, Yasuo

, p. 7 - 12 (2007/10/03)

AlCl3-mediated decomposition of N-phenoxybenzamide derivatives in dichloromethane mainly leads to regioselective intramolecular migration of benzamido group from the oxygen to the ortho position of the phenyl group via electron-deficient nitrogen intermediates.

The mechanism of electrochemical reduction of N-haloamides in acetonitrile: trapping of intermediate amide anions and father-son protonation

Berube, Denis,Lessard, Jean

, p. 1127 - 1142 (2007/10/02)

The electrochemical reduction of N-haloamides (ZCONRX) in acetonitrile involves two consecutive one-electron transfers and generates the amide anions.Attempts to trap the intermediate amidyl radical resulting from first electron transfer were unssuccesful.In the case of the N-halo-N-hydroamides (R=H), the amide anion formed at the electrode abstracts a proton from an incoming N-halo-N-hydroamide molecule to give the parent amide and the conjugate base of the N-haloamide (father-son protonation).Thus, half of the N-halo-N-hydroamide reaching the electrode is reduced, the other half being converted to its conjugate base.In acetonitrile-LiClO4 (0.2 M) containing 0.2percent water, the conjugate base is reducible and polarograms therefore show two waves (irreversible and diffusion controlled) of equivalent intensities due respectively to the reduction of the N-halo-N-hydroamide and to the reduction of its conjugate base.In the case of the N-chloro-N-alkyl(aryl)amides (X=Cl, R=alkyl or aryl), the amide anion abstracts a proton from the medium to give the parent amide and anionic species that react with the starting N-chloroamide regenerating the amide anion.Hence, the coulometric results are low (0.5 F/mol).However, in the presence of acetic acid, the reduction consumes 2 F/mol as expected.The N-alkylamide anion has been trapped by N-alkylation and N-acylation.The voltammograms of N-chloro-N-alkyl(aryl)amides show multiple waves on mercury and platinum due to passivation-adsorption phenomena but a single wave on vitreous carbon.

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