3-Hydroxy-4'-methoxy-2-naphthanilide

Base Information

• Chemical Name: 3-Hydroxy-4'-methoxy-2-naphthanilide
• CAS No.: 92-79-5
• Molecular Formula: C18H15NO3
• Molecular Weight: 293.322
• Hs Code.: 2924299090
• European Community (EC) Number: 202-190-2
• NSC Number: 37613
• UNII: T0MUF32GX6
• DSSTox Substance ID: DTXSID2059067
• Nikkaji Number: J73.259A
• Wikidata: Q27289515
• ChEMBL ID: CHEMBL63883
• Mol file: 92-79-5.mol

Synonyms:92-79-5;3-Hydroxy-4'-methoxy-2-naphthanilide;Naphthol AS-RL;Naphtazol RL;Naphtol AS-RL;Naphtanilide RL;Azoic Coupling Component 11;Azonaphtol PA;Naphthanil RL;Naphthoide RL;Naphtoelan RL;Azoground RL;Solunaptol PAL;Acna Naphthol R;Cibanaphthol RBL;Irganaphthol RBL;Sanatol RL;Azotol PA;Anthonaphthol MRL;Celcot RBL;Naphthol AS-RL Supra;Amarthol AS-RL;Daito Grounder RL;Hiltonaphthol AS-RL;3-hydroxy-N-(4-methoxyphenyl)naphthalene-2-carboxamide;Naphtanilide RL Supra;Naphtol AS-RL Supra;Amanil Naphthol AS-RL;Naphthol AS-RL Dispersible;C.I. Azoic Coupling Component 11;2-Naphth-p-anisidide, 3-hydroxy-;2-Naphthalenecarboxamide, 3-hydroxy-N-(4-methoxyphenyl)-;C.I. 37535;3-Hydroxy-N-(4-methoxyphenyl)-2-naphthamide;NSC 37613;3-Hydroxy-2-naphthoyl-p-anisidide;EINECS 202-190-2;UNII-T0MUF32GX6;T0MUF32GX6;CHEMBL63883;C.I.Azoic Coupling Component 11;2-Hydroxy-3-((4-methoxyphenyl)carbamoyl)naphthalene;2-Hydroxy-3-[(4-methoxyphenyl)carbamoyl]naphthalene;NSC-37613;EC 202-190-2;Oprea1_801037;cid_66721;MLS001194832;SCHEMBL2048865;3-Hydroxy-2-naphth-p-anisidide;DTXSID2059067;HMS2859A04;1-Hydroxy-3-Naphthoyl-P-Anisidine;NSC37613;BDBM50091987;STK362990;3-hydroxy-4'-methoxy-2-naphthanilid;AKOS001572915;NCGC00245832-01;CI 37535;SMR000554652;C.I.37535;LS-185506;CS-0366019;EU-0068113;FT-0631457;3-Hydroxy-N-(4-methoxyphenyl)-2-naphthamide #;SR-01000400026;SR-01000400026-1;W-109342;Q27289515;3-Hydroxy-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide

Chemical Property of 3-Hydroxy-4'-methoxy-2-naphthanilide

Chemical Property:

• Melting Point: 229~230℃
• Boiling Point: 426.8 °C at 760 mmHg
• PKA: 8.75±0.40(Predicted)
• Flash Point: 211.9 °C
• PSA: 58.56000
• Density: 1.304 g/cm³
• LogP: 3.87930
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 293.10519334
• Heavy Atom Count: 22
• Complexity: 379

Purity/Quality:

99% ^*data from raw suppliers

2-HYDROXY-3-NAPHTHOYL-P-ANISIDIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)NC(=O)C2=CC3=CC=CC=C3C=C2O

Technology Process of 3-Hydroxy-4'-methoxy-2-naphthanilide

There total 7 articles about 3-Hydroxy-4'-methoxy-2-naphthanilide 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: 80.0%

4-methoxy-aniline (104-94-9) + 3-Hydroxy-2-naphthoic acid (92-70-6) → naphthol AS-RL (92-79-5)

Guidance literature:

With ortho-iodophenylboronic acid; In toluene; for 20h; Inert atmosphere; Reflux; Sealed tube;

Reference yield: 45.0%

3-hydroxy-2-naphthoyl chloride (1734-00-5) + 4-methoxy-aniline (104-94-9) → naphthol AS-RL (92-79-5)

Guidance literature:

In tetrahydrofuran; for 1h; Reflux;

DOI:10.1016/j.bmc.2012.09.056

Reference yield:

4-amino-phenol (123-30-8) → naphthol AS-RL (92-79-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / acetonitrile / 24 h / 20 °C

2: trichlorophosphate / chlorobenzene / 0.25 h / Microwave irradiation

With sodium hydride; trichlorophosphate; In chlorobenzene; acetonitrile;

DOI:10.3390/molecules23071635

upstream raw materials:

4-methoxy-aniline

3-Hydroxy-2-naphthoic acid

4-Methoxyphenyl isothiocyanate

3-hydroxy-2-naphthoyl chloride

Downstream raw materials:

8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid p-anisidide

3-(4-methoxy-phenyl)-2,2-dioxo-2,3-dihydro-2λ⁶-naphtho[2,3-e][1,2,3]oxathiazin-4-one

3-hydroxy-N-(4-methoxyphenyl)-4-[(4-methoxyphenyl)azo]naphthalene-2-carboxamide

4-(4-Diethylamino-phenylazo)-3-hydroxy-naphthalene-2-carboxylic acid (4-methoxy-phenyl)-amide

Refernces

• 1、 Kos, Jiri,Kapustikova, Iva,Clements, Carol,Gray, Alexander I.,Jampilek, Josef. "3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity". . p. 887 - 892. Retrieved 2018/02/12.
• 2、 Gonec, Tomas,Kralova, Katarina,Pesko, Matus,Jampilek, Josef. "Antimycobacterial N-alkoxyphenylhydroxynaphthalenecarboxamides affecting photosystem II". . p. 1881 - 1885. Retrieved 2017/04/07.