3-Hydroxy-3'-nitro-2-naphthanilide

Base Information

• Chemical Name: 3-Hydroxy-3'-nitro-2-naphthanilide
• CAS No.: 135-65-9
• Molecular Formula: C17H12N2O4
• Molecular Weight: 308.293
• Hs Code.: DERIVATION
• European Community (EC) Number: 205-209-2
• NSC Number: 37168
• UNII: 8K775B2J7E
• DSSTox Substance ID: DTXSID3044544
• Nikkaji Number: J5.612J
• Wikidata: Q27270667
• ChEMBL ID: CHEMBL65374
• Mol file: 135-65-9.mol

Synonyms:3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide

Chemical Property of 3-Hydroxy-3'-nitro-2-naphthanilide

Chemical Property:

• Appearance/Colour: yellow to brown powder
• Vapor Pressure: 0.001Pa at 20℃
• Melting Point: 246-247 °C
• Boiling Point: 448 °C at 760 mmHg
• PKA: 8.65±0.40(Predicted)
• Flash Point: 224.7 °C
• PSA: 95.15000
• Density: 1.449 g/cm³
• LogP: 4.30210
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 308.07970687
• Heavy Atom Count: 23
• Complexity: 450

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-3'-nitro-2-naphthanilide >95.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36
• Safety Statements: 36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C(=CC2=C1)C(=O)NC3=CC(=CC=C3)[N+](=O)[O-])O

Technology Process of 3-Hydroxy-3'-nitro-2-naphthanilide

There total 2 articles about 3-Hydroxy-3'-nitro-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: 58.0%

3-nitro-aniline (99-09-2) + 3-Hydroxy-2-naphthoic acid (92-70-6) → 3-hydroxy-3'-nitro-2-naphthanilide (135-65-9)

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-nitro-aniline (99-09-2) → 3-hydroxy-3'-nitro-2-naphthanilide (135-65-9)

Guidance literature:

With toluene;

Reference yield: 92.0%

3-hydroxy-3'-nitro-2-naphthanilide (135-65-9) → C17H14N2O3

Guidance literature:

3-hydroxy-3'-nitro-2-naphthanilide; With tris(pentafluorophenyl)borate; methylphenylsilane; In toluene; at 27 - 50 ℃; for 25h; Inert atmosphere; Sealed tube;

With tetrabutyl ammonium fluoride; In toluene; at 0 - 27 ℃; for 1h; chemoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.8b03014

upstream raw materials:

3-hydroxy-2-naphthoyl chloride

3-nitro-aniline

3-Hydroxy-2-naphthoic acid

Downstream raw materials:

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

3,3'-dihydroxy-4,4'-biphenyl-4,4'-diyl-bis-azo-di-[2]naphthoic acid bis-(3-nitro-anilide)

4-(9,10-dioxo-9,10-dihydro-[2]anthrylazo)-3-hydroxy-[2]naphthoic acid-(3-nitro-anilide)

3-hydroxy-2-naphthoic acid 3'-aminoanilide

Refernces

• 1、 Ni, Jizhi,Oguro, Tsubasa,Sawazaki, Taka,Sohma, Youhei,Kanai, Motomu. "Hydroxy Group Directed Catalytic Hydrosilylation of Amides". supporting information. p. 7371 - 7374. Retrieved 2018/11/25.
• 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.