3-Hydroxy-2-naphthanilide

Base Information

• Chemical Name: 3-Hydroxy-2-naphthanilide
• CAS No.: 92-77-3
• Molecular Formula: C17H13NO2
• Molecular Weight: 263.296
• Hs Code.: H13NO2 MOL WT. 263.30
• European Community (EC) Number: 202-188-1
• NSC Number: 45173
• UNII: V3ZU6E76NB
• DSSTox Substance ID: DTXSID1052618
• Nikkaji Number: J1.928.650I,J4.660D
• Wikipedia: Naphthol_AS
• Wikidata: Q25387080
• ChEMBL ID: CHEMBL63731
• Mol file: 92-77-3.mol

Synonyms:3-hydroxy-2-naphthanilide;naphthol AS;naphthol AS, 14C-labeled cpd;naphthol AS, monosodium salt

Chemical Property of 3-Hydroxy-2-naphthanilide

Chemical Property:

• Appearance/Colour: beige powder
• Melting Point: 246-248 °C(lit.)
• Refractive Index: 1.4500 (estimate)
• Boiling Point: 391.774 °C at 760 mmHg
• PKA: 9.70(at 25℃)
• Flash Point: 190.738 °C
• PSA: 49.33000
• Density: 1.311 g/cm³
• LogP: 3.87070
• Storage Temp.: Refrigerator
• Solubility.: Solubility Insoluble in water; sparingly soluble in ethanol
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 263.094628657
• Heavy Atom Count: 20
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

Naphtol AS ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 36/37-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC(=O)C2=CC3=CC=CC=C3C=C2O
• Description: Naphtol AS is a coupling agent in cotton dying. Occupational dermatitis was reported in a woman involved in needlework, probably sensitized from occupational contact with clothes.
• Uses: Naphtol AS was used as off-the-shelf color-based anion sensors in organic solvents.

Technology Process of 3-Hydroxy-2-naphthanilide

There total 16 articles about 3-Hydroxy-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: 91.0%

aniline (62-53-3) + 3-Hydroxy-2-naphthoic acid (92-70-6) → 2,3-oxynaphthoic acid phenylamide (92-77-3)

Guidance literature:

With phosphorus trichloride; at 184 ℃; for 2h; Product distribution; Mechanism; var. catalysts, var. time;

Reference yield:

4-(3-aminophenetyl)-4',4-dimethyltriphenylamine + 3-Hydroxy-2-naphthoic acid (92-70-6) → 2,3-oxynaphthoic acid phenylamide (92-77-3)

Guidance literature:

With anhydrous phosphorus trichloride; In 1,4-dioxane; ethyl acetate; toluene;

Reference yield:

2,4-bis(anilino)-1,3-diphenyl-1,3,2,4-diazadiphosphetidine (18440-21-6,79957-34-9) + 3-Hydroxy-2-naphthoic acid (92-70-6) → 2,3-oxynaphthoic acid phenylamide (92-77-3)

Guidance literature:

With toluene;

DOI:10.1021/ja01208a001

upstream raw materials:

3-acetoxy-2-naphthoic acid

3-(benzoyloxy)-2-naphthoic acid

phenyl isothiocyanate

3-Hydroxy-2-naphthoic acid

Downstream raw materials:

3-methoxy-[2]naphthoic acid anilide

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

1-(4-nitrophenylazo)-2-hydroxynaphthalene-3-carboxanilide

4-(2,4-dinitro-phenylazo)-3-hydroxy-[2]naphthoic acid anilide

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.