2-Hydroxy-3-iodo-1,4-naphthoquinone

Base Information

• Chemical Name: 2-Hydroxy-3-iodo-1,4-naphthoquinone
• CAS No.: 572874-62-5
• Molecular Formula: C10H5IO3
• Molecular Weight: 300.052
• DSSTox Substance ID: DTXSID701286464
• Nikkaji Number: J1.930.453A,J904.570H
• Pharos Ligand ID: F2A6PXHNL3J5
• ChEMBL ID: CHEMBL4292211
• Mol file: 572874-62-5.mol

Synonyms:2-Hydroxy-3-iodonaphthalene-1,4-dione;2-hydroxy-3-iodo-1,4-naphthoquinone;35135-38-7;CHEMBL4292211;SCHEMBL10068411;DTXSID701286464;AMY27838;BDBM50464477;MFCD18448649;3-Iodo-4-hydroxynaphthalene-1,2-dione;4-Hydroxy-3-iodo-1,2-naphthalenedione;572874-62-5;1,4-Naphthalenedione, 2-hydroxy-3-iodo-;N16907

Chemical Property of 2-Hydroxy-3-iodo-1,4-naphthoquinone

Chemical Property:

• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 299.92834
• Heavy Atom Count: 14
• Complexity: 332

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(C(=O)C2=O)I)O

Technology Process of 2-Hydroxy-3-iodo-1,4-naphthoquinone

There total 12 articles about 2-Hydroxy-3-iodo-1,4-naphthoquinone 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: 66.0%

3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide (117560-06-2) + N-methylaniline (100-61-8) → benzhydrylidene(methyl)amine (552-82-9) + 2-iodo-3-phenoxy-1,4-naphthoquinone (160246-88-8) + 3-iodo-4-hydroxy-1,2-naphthoquinone (572874-62-5)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃;

DOI:10.1021/jo0343679

Reference yield: 55.0%

phenethylamine (64-04-0) + 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide (117560-06-2) → (N-phenyl)phenylethylamine (1739-00-0) + 2-iodo-3-phenoxy-1,4-naphthoquinone (160246-88-8) + 3-iodo-4-hydroxy-1,2-naphthoquinone (572874-62-5) + Z,E-3-iodo-4-hydroxy-1[(2-phenylethyl)imino]-2-naphthalenone (571166-63-7)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; Further byproducts given;

DOI:10.1021/jo0343679

Reference yield: 55.0%

p-toluidine (106-49-0,12221-03-3) + 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide (117560-06-2) → 4-methyldiphenylamine (620-84-8) + 2-iodo-3-phenoxy-1,4-naphthoquinone (160246-88-8) + 3-iodo-4-hydroxy-1,2-naphthoquinone (572874-62-5)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃;

DOI:10.1021/jo0343679

upstream raw materials:

p-toluidine

3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide

4-methoxy-aniline

phenethylamine

Downstream raw materials:

2-hydroxy-3-iodonaphthalene-1,4-dione

Refernces

• 1、 Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros,Tsanakopoulou, Maria. "Studies on the reactivity of aryliodonium ylides of 2-hydroxy-1,4-naphthoquinone: Reactions with amines". . p. 5627 - 5631. Retrieved 2007/10/03.