2-(oxiran-2-yl)-3-(prop-2-en-1-yl)naphthalene-1,4-dione

Base Information

• Chemical Name: 2-(oxiran-2-yl)-3-(prop-2-en-1-yl)naphthalene-1,4-dione
• CAS No.: 86499-02-7
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.258
• Mol file: 86499-02-7.mol

Synonyms:1,4-Naphthalenedione,2-oxiranyl-3-(2-propenyl)- (9CI); NSC 370934

Chemical Property of 2-(oxiran-2-yl)-3-(prop-2-en-1-yl)naphthalene-1,4-dione

Chemical Property:

• Vapor Pressure: 1.75E-06mmHg at 25°C
• Boiling Point: 396.1°Cat760mmHg
• Flash Point: 177.5°C
• Density: 1.294g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(oxiran-2-yl)-3-(prop-2-en-1-yl)naphthalene-1,4-dione

There total 8 articles about 2-(oxiran-2-yl)-3-(prop-2-en-1-yl)naphthalene-1,4-dione 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: 62.0%

2-allyl-1,4-dimethoxy-3-oxiranylnaphtalene (86498-93-3) → 2-Allyl-3-oxiranyl-[1,4]naphthoquinone (86499-02-7)

Guidance literature:

With pyridine-2-carboxylic acid, Ag(II) salt; In water; benzene; Ambient temperature;

DOI:10.1016/S0040-4020(01)91854-X

Reference yield:

1,4-dimethoxynaphthalene (10075-62-4) → 2-Allyl-3-oxiranyl-[1,4]naphthoquinone (86499-02-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / HBr / acetic acid / 20 h / Ambient temperature

2: 94 percent / bromine / CCl₄ / 168 h

3: 87 percent / potassium phenylselenite, dipotassium hydrogen phosphate, 18-crown-6 / acetonitrile / 22 h / Heating

4: 97 percent / toluene-p-sulfonic acid / benzene / 3 h / Heating

5: 1.) n-BuLi, CuI, (CH₃)2Se / 1.) THF, hexane -78 deg C, 3 h 2.) THF, hexane -78 deg C 70 min then rt 1 h

6: HCl / H₂O; tetrahydrofuran; hexane / 15 h / Ambient temperature

7: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature

8: 62 percent / silver(II) dipicolinate / benzene; H₂O / Ambient temperature

With hydrogenchloride; sodium hydroxide; dipotassium hydrogenphosphate; copper(l) iodide; n-butyllithium; 18-crown-6 ether; dimethylselenide; pyridine-2-carboxylic acid, Ag(II) salt; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; bromine; Potassium benzeneselenite; toluene-4-sulfonic acid; In tetrahydrofuran; tetrachloromethane; hexane; water; acetic acid; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)91854-X

Reference yield:

2-(bromomethyl)-1,4-dimethoxynaphthalene (79971-24-7) → 2-Allyl-3-oxiranyl-[1,4]naphthoquinone (86499-02-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / bromine / CCl₄ / 168 h

2: 87 percent / potassium phenylselenite, dipotassium hydrogen phosphate, 18-crown-6 / acetonitrile / 22 h / Heating

3: 97 percent / toluene-p-sulfonic acid / benzene / 3 h / Heating

4: 1.) n-BuLi, CuI, (CH₃)2Se / 1.) THF, hexane -78 deg C, 3 h 2.) THF, hexane -78 deg C 70 min then rt 1 h

5: HCl / H₂O; tetrahydrofuran; hexane / 15 h / Ambient temperature

6: 93 percent / NaOH, TEBA / tetrahydrofuran / 4 h / Ambient temperature

7: 62 percent / silver(II) dipicolinate / benzene; H₂O / Ambient temperature

With hydrogenchloride; sodium hydroxide; dipotassium hydrogenphosphate; copper(l) iodide; n-butyllithium; 18-crown-6 ether; dimethylselenide; pyridine-2-carboxylic acid, Ag(II) salt; N-benzyl-N,N,N-triethylammonium chloride; bromine; Potassium benzeneselenite; toluene-4-sulfonic acid; In tetrahydrofuran; tetrachloromethane; hexane; water; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)91854-X

upstream raw materials:

2-allyl-1,4-dimethoxy-3-oxiranylnaphtalene

1,4-dimethoxynaphthalene

2-(bromomethyl)-1,4-dimethoxynaphthalene

2-bromo-3-(2-bromomethyl)-1,4-dimethoxynaphthalene

Refernces