2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy-

Base Information

• Chemical Name: 2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy-
• CAS No.: 5442-40-0
• Molecular Formula: C17H12 Cl N O2
• Molecular Weight: 297.741
• Hs Code.: 2924299090
• European Community (EC) Number: 226-636-0
• NSC Number: 50683,12969
• UNII: 5K5YW3Y3C4
• DSSTox Substance ID: DTXSID8063888
• Nikkaji Number: J73.256G
• Wikidata: Q81991071
• ChEMBL ID: CHEMBL528589
• Mol file: 5442-40-0.mol

Synonyms:5442-40-0;N-(3-Chlorophenyl)-3-hydroxynaphthalene-2-carboxamide;2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy-;TCMDC-124171;C.I. Azoic Coupling Component 22;2-Naphthanilide, 3'-chloro-3-hydroxy-;C.I. 37511;NSC 12969;GNF-Pf-2634;5K5YW3Y3C4;EINECS 226-636-0;NSC 50683;NSC-12969;NSC-50683;N-(3-Chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide;2-HYDROXY-3-NAPHTHOYL-M-CHLOROANILIDE;UNII-5K5YW3Y3C4;Oprea1_159669;Oprea1_571684;CHEMBL528589;SCHEMBL2129113;DTXSID8063888;3-Hydroxy-naphthalene-2-carboxylic acid (3-chloro-phenyl)-amide;NSC12969;NSC50683;AKOS000592805;CCG-275204;C.I.37511;N-(3-Chlorophenyl)-3-hydroxy-2-naphthamide;SJ000142233;SR-01000400032;SR-01000400032-1;N-(3-chlorophenyl)-3-hydroxy-naphthalene-2-carboxamide

Chemical Property of 2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy-

Chemical Property:

• Vapor Pressure: 1.77E-07mmHg at 25°C
• Boiling Point: 415°Cat760mmHg
• Flash Point: 204.8°C
• PSA: 49.33000
• Density: 1.399g/cm³
• LogP: 4.52410
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 297.0556563
• Heavy Atom Count: 21
• Complexity: 376

Purity/Quality:

99%, ^*data from raw suppliers

2-HYDROXY-3-NAPHTHOYL-META-CHLOROANILIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C(=CC2=C1)C(=O)NC3=CC(=CC=C3)Cl)O

Technology Process of 2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy-

There total 4 articles about 2-Naphthalenecarboxamide, N-(3-chlorophenyl)-3-hydroxy- 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: 69.0%

3-chloro-aniline (108-42-9) + 3-Hydroxy-2-naphthoic acid (92-70-6) → N-(3-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide (5442-40-0)

Guidance literature:

With phosphorus trichloride; In chlorobenzene; at 100 - 130 ℃; for 0.75h; Microwave irradiation;

DOI:10.3390/molecules18077977

Reference yield:

3-hydroxy-2-naphthoyl chloride (1734-00-5) + 3-chloro-aniline (108-42-9) → N-(3-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide (5442-40-0)

Guidance literature:

With sodium acetate; In N,N-dimethyl-formamide; chlorobenzene; at 5 - 50 ℃;

Reference yield:

3-Hydroxy-2-naphthoic acid (92-70-6) → N-(3-chlorophenyl)-3-hydroxynaphthalene-2-carboxamide (5442-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 1 h / Reflux

2: tetrahydrofuran / 1 h / Reflux

With thionyl chloride; In tetrahydrofuran;

DOI:10.1016/j.bmc.2012.09.056

upstream raw materials:

3-chloro-aniline

3-Hydroxy-2-naphthoic acid

3-hydroxy-2-naphthoyl chloride

Downstream raw materials:

C₂₀H₁₆ClNO₃

Refernces

• 1、 Kos, Jiri,Zadrazilova, Iveta,Pesko, Matus,Keltosova, Stanislava,Tengler, Jan,Gonec, Tomas,Bobal, Pavel,Kauerova, Tereza,Oravec, Michal,Kollar, Peter,Cizek, Alois,Kralova, Katarina,Jampilek, Josef. "Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides". . p. 7977 - 7997. Retrieved 2013/08/23.
• 2、 Vattipalli, Ramya,Shirodkar, Prabhakar Y.,Somani, Rakesh R.,Kadam, Vilasrao J.. "Synthesis and β-adrenergic blocking activity of naphthyloxypropylamines". experimental part. p. 1587 - 1590. Retrieved 2009/04/07.