N-(2,6-dimethyl-4-oxo-1-cyclohexa-2,5-dienylidene)acetamide

Base Information

• Chemical Name: N-(2,6-dimethyl-4-oxo-1-cyclohexa-2,5-dienylidene)acetamide
• CAS No.: 74827-88-6
• Molecular Formula: C10H11 N O2
• Molecular Weight: 177.203
• Mol file: 74827-88-6.mol

Synonyms:2,6-Dimethyl-N-acetyl-p-benzoquinoneimine

Chemical Property of N-(2,6-dimethyl-4-oxo-1-cyclohexa-2,5-dienylidene)acetamide

Chemical Property:

• Vapor Pressure: 0.0045mmHg at 25°C
• Boiling Point: 277.5°C at 760 mmHg
• Flash Point: 111.8°C
• PSA: 46.50000
• Density: 1.09g/cm³
• LogP: 1.44920

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-(2,6-dimethyl-4-oxo-1-cyclohexa-2,5-dienylidene)acetamide

There total 3 articles about N-(2,6-dimethyl-4-oxo-1-cyclohexa-2,5-dienylidene)acetamide 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: 41.0%

N-(4-hydroxy-2,6-dimethylphenyl)acetamide (6337-56-0) → N-acetyl-3,5-dimethyl-1,4-benzoquinone imine (74827-88-6)

Guidance literature:

With lead(IV) acetate; In ethyl acetate; at 45 ℃;

DOI:10.1021/jm00185a001

Reference yield:

3,5-dimethyl-4-aminophenol (3096-70-6) → N-acetyl-3,5-dimethyl-1,4-benzoquinone imine (74827-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaOAc / H₂O / 1 h

2: 41 percent / Pb(OAc)4 / ethyl acetate / 45 °C

With lead(IV) acetate; sodium acetate; In water; ethyl acetate;

DOI:10.1021/jm00185a001

Reference yield:

3,5-Dimethylphenol (108-68-9,50356-23-5) → N-acetyl-3,5-dimethyl-1,4-benzoquinone imine (74827-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) diazotized sulfanilic acid, 2.) sodium dithionite / 1.) 1 h, 2.) 65 deg C to 70 deg C

2: 89 percent / NaOAc / H₂O / 1 h

3: 41 percent / Pb(OAc)4 / ethyl acetate / 45 °C

With lead(IV) acetate; sodium dithionite; 4-sulfobenzenediazonium; sodium acetate; In water; ethyl acetate;

DOI:10.1021/jm00185a001

upstream raw materials:

N-(4-hydroxy-2,6-dimethylphenyl)acetamide

3,5-dimethyl-4-aminophenol

3,5-Dimethylphenol

Downstream raw materials:

4-acetamido-4-anilino-3,5-dimethyl-2,5-cyclohexadien-1-one

N-(1-isopropoxy-2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide

N-(2,6-dimethyl-4-oxo-1-pentyloxycyclohexa-2,5-dien-1-yl)acetamide

N-(1-butoxy-2,6-dimethyl-4-oxocyclohexa-2,5-dien-1-yl)acetamide

Refernces

• 1、 Konovalova,Avdeenko,Ledeneva,Yusina,Pirozhenko,Shishkin,Palamarchuk. "Thiocyanation of N-aryl, N-acetyl, and N-[arylsulfonylimino(methyl)methyl] derivatives of 1,4-benzoquinone monoimine". . p. 635 - 646. Retrieved 2014/07/08.
• 2、 Fernando,Calder,Ham. "Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines". . p. 1153 - 1158. Retrieved 2007/10/02.