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:

98%,99%, ^*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

• 1、 Akhir, Abdul,Ansari, Shabina B.,Chopra, Sidharth,Kaul, Grace,Lal, Jhajan,Reddy, Damodara N.. "Bio-evaluation of fluoro and trifluoromethyl-substituted salicylanilides against multidrug-resistant S. aureus". . p. 2301 - 2315. Retrieved 2021/10/30.
• 2、 Bai, Jin,Li, Shangzhang,Li, Wanfang,Qu, Erdong,Zheng, Yan. "Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides". supporting information. . Retrieved 2021/12/27.