Salicylanilide

Base Information

• Chemical Name: Salicylanilide
• CAS No.: 87-17-2
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.236
• Hs Code.: DERIVATION
• European Community (EC) Number: 201-727-8
• NSC Number: 755836,14881
• UNII: LHP8NEY345
• DSSTox Substance ID: DTXSID7021784
• Nikkaji Number: J4.273K
• Wikipedia: Salicylanilide
• Wikidata: Q3469751
• NCI Thesaurus Code: C84142
• Metabolomics Workbench ID: 66934
• ChEMBL ID: CHEMBL82970
• Mol file: 87-17-2.mol

Synonyms:salicylanilide;salicylanilide, sodium salt;salicylanilide, zinc salt

Chemical Property of Salicylanilide

Chemical Property:

• Appearance/Colour: greyish-brownish powder
• Melting Point: 136-138 °C
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 294.3 °C at 760 mmHg
• PKA: 7.11±0.10(Predicted)
• Flash Point: 131.8 °C
• PSA: 49.33000
• Density: 1.278 g/cm³
• LogP: 2.71750
• Storage Temp.: -20°C
• Solubility.: H2O: slightly soluble
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 213.078978594
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

97% ^*data from raw suppliers

Salicylanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C1=CC=C(C=C1)NC(=O)C2=CC=CC=C2O
• Uses: antipyretic, fungicide Anti-mildew, fungicide. Salicylanilides are compounds of varying biological activity ranging from anti-inflammatory agents to antiviral and antimicrobial agents.

Technology Process of Salicylanilide

There total 64 articles about Salicylanilide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

aniline (62-53-3) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → salicylanilide (87-17-2)

Guidance literature:

With phosphorus trichloride; In 5,5-dimethyl-1,3-cyclohexadiene; for 0.55h; Microwave irradiation;

DOI:10.1080/00397911.2010.481745

Reference yield: 98.0%

salicylaldehyde (90-02-8) + aniline (62-53-3) → salicylanilide (87-17-2)

Guidance literature:

With [{(CH₂SiMe₂){(2,6-iPr₂C₆H₃)N}2}Y{N(SiMe₃)2}(THF)]; In toluene; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.200901015

Reference yield: 94.0%

bromobenzene (108-86-1,52753-63-6) + salicylamide (65-45-2) → salicylanilide (87-17-2)

Guidance literature:

With di-tert-butyl{2′-isopropoxy-[1,1′-binaphthalen]-2-yl}phosphane; caesium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tert-butyl alcohol; at 100 ℃; for 20h; Inert atmosphere;

DOI:10.1021/jo3005827

upstream raw materials:

phenyl N-phenylcarbamate

sodium phenoxide

2-phenylcarbamoyloxy-benzoic acid methyl ester

2-(2-hydroxy-benzoyloxy)-benzoic acid anilide

Downstream raw materials:

6,6'-dihydroxy-3,3'-methanediyl-di-benzoic acid dianilide

2-hydroxy-5-phenylazo-benzoic acid anilide

Dibromsalan

2-(benzothiazol-2-yl)phenol

Refernces

Synthesis and Biological Activity of a Series of Diaryl-Substituted α-Cyano-β-hydroxypropenamides, a New Class of Anthelmintic Agents

10.1021/jm00115a020

The study investigates the synthesis and biological activity of a series of a-cyano-B-hydroxypropenamides as potential anthelmintic agents. The lead compound, a-cyano-j3-hydroxy-N-[4-(trifluoromethyl)phenyl]-3-[4-(trifluoromethyl)phenyl]propenamide (1), demonstrated good activity against the nematode Nematospirodes dubius in mice and effectively reduced the hematophagous nematode Haemonchus contortus in sheep. However, it showed a narrow spectrum of activity against other parasitic nematodes. The study also explored the structure-activity relationships of various analogues, finding that certain substituents, such as halogens and electron-withdrawing groups, retained or enhanced activity. Mechanism of action studies using Ascaris mitochondria suggested that compound 1 acts as an uncoupler of oxidative phosphorylation, similar to the salicylanilide class of anthelmintics. The research aims to identify novel anthelmintic agents effective against resistant and non-resistant parasites, addressing the growing issue of resistance to existing treatments.