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

Base Information

• Chemical Name: 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)-
• CAS No.: 135-61-5
• Deprecated CAS: 12221-06-6,12235-62-0,12235-62-0
• Molecular Formula: C18H15NO2
• Molecular Weight: 277.323
• Hs Code.: 2924299090
• European Community (EC) Number: 205-205-0
• NSC Number: 37188
• DSSTox Substance ID: DTXSID6059653
• Nikkaji Number: J5.608A
• Wikidata: Q72493605
• Mol file: 135-61-5.mol

Synonyms:3-hydroxy-4'-nitro-2-naphthanilide chloroacetate;naphthol AS-D

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

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 5.83E-07mmHg at 25°C
• Melting Point: 196-198 °C
• Refractive Index: 1.715
• Boiling Point: 399.689 °C at 760 mmHg
• PKA: 8.73±0.40(Predicted)
• Flash Point: 195.525 °C
• PSA: 49.33000
• Density: 1.277 g/cm³
• LogP: 4.17910
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 277.110278721
• Heavy Atom Count: 21
• Complexity: 370

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-2''-methyl-2-naphthanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC(=O)C2=CC3=CC=CC=C3C=C2O

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

There total 6 articles about 2-Naphthalenecarboxamide, 3-hydroxy-N-(2-methylphenyl)- 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: 74.0%

o-toluidine (95-53-4) + 3-Hydroxy-2-naphthoic acid (92-70-6) → naphthol ASD (135-61-5)

Guidance literature:

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

DOI:10.3390/molecules18077977

Reference yield:

nitrilotriacetic acid (139-13-9,80751-51-5) + o-toluidine (95-53-4) → naphthol ASD (135-61-5)

Guidance literature:

With sodium carbonate; In anhydrous phosphorus trichloride; water;

Reference yield:

3-hydroxy-2-naphthoic acid methyl ester (883-99-8) → naphthol ASD (135-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: water; sodium hydroxide / ethanol / 6 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In ethanol; dichloromethane;

DOI:10.1002/adsc.201901573

upstream raw materials:

o-toluidine

3-Hydroxy-2-naphthoic acid

2-tolyl isothiocyanate

nitrilotriacetic acid

Downstream raw materials:

3-o-tolyl-naphtho[2,3-e][1,3]oxazine-2,4-dione

dimethyl 2-[2-hydroxy-3-(2-methylphenylcarbamoyl)naphthalen-1-yl]-but-2-enedioate

dimethyl 2-(methoxycarbonylmethyl)-4-oxo-3-o-tolyl-3,4-dihydro-2H-naphtho[2,3-e][1,3]oxazine-2-carboxylate

diethyl 2-[2-hydroxy-3-(2-methylphenylcarbamoyl)naphthalen-1-yl]-but-2-enedioate

Refernces

• 1、 Cai, Jinhui,Hu, Xu-Dong,Liu, Wen-Bo,Wang, Zhen-Kai,Yao, Fei,Zhang, Yun-Hao. "Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade". supporting information. . Retrieved 2020/02/25.
• 2、 Fujita, Satoshi,Momiyama, Masayoshi,Kondo, Yasumitsu,Kagiyama, Naoto,Hori, Samuel H.,Toru, Takeshi. "Fluorescent substrates for potential use in enzyme-linked immunosorbent assay of membrane-bound nucleic acids". . p. 1347 - 1353. Retrieved 2007/10/02.