o-Quinomethane

Base Information

• Chemical Name: o-Quinomethane
• CAS No.: 27890-67-1
• Molecular Formula: C7H6 O
• Molecular Weight: 106.124
• DSSTox Substance ID: DTXSID901336114
• Metabolomics Workbench ID: 58244
• Nikkaji Number: J302.681G
• Wikidata: Q27123420
• Mol file: 27890-67-1.mol

Synonyms:o-quinomethane;o-quinone methide;6-methylidenecyclohexa-2,4-dien-1-one;o-Quinonemethide;6-methylene-2,4-cyclohexadien-1-one;SCHEMBL522896;CHEBI:52409;DTXSID901336114;Q27123420

Chemical Property of o-Quinomethane

Chemical Property:

• Vapor Pressure: 0.257mmHg at 25°C
• Boiling Point: 204.9°Cat760mmHg
• Flash Point: 77.3°C
• Density: 1.01g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 106.041864811
• Heavy Atom Count: 8
• Complexity: 185

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1C=CC=CC1=O

Technology Process of o-Quinomethane

There total 22 articles about o-Quinomethane 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:

3-methoxycarbonyl-4H-1,2-benzoxazine (538342-16-4) → methyl cyanoformate (17640-15-2) + 6-methylene-cyclohexa-2,4-dienone (27890-67-1)

Guidance literature:

With vinyloxycyclohexane; In ⁽²⁾H₈-toluene; at 80 ℃; Further Variations:; Solvents; Temperatures; Kinetics;

DOI:10.1021/jo702246w

Reference yield:

3-phenyl-4H-1,2-benzoxazine (127383-38-4) → 6-methylene-cyclohexa-2,4-dienone (27890-67-1) + benzonitrile (100-47-0)

Guidance literature:

at 90 ℃; other benzoxazines;

Reference yield:

benzo[1,4]dioxine (255-37-8) → 6-methylene-cyclohexa-2,4-dienone (27890-67-1) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

at 776.9 ℃; Product distribution; very low pressure pyrolysis at 550-1210 K; formation of o-quinone methide intermediate; conversion of o-quinone methide to benzene at higher temperatures; mechanism; MS study;

DOI:10.1039/a800189h

upstream raw materials:

2-(methoxymethyl)phenol

salicylic alcohol

methanol

chromane

Downstream raw materials:

2-(methoxymethyl)phenol

o-Hydroxyethylbenzene

ortho-cresol

3,4-dihydro-2-methyl-2H-1-benzopyran

Refernces

• 1、 Letulle,Guenot,Ripoll. "The syntheses of 6-methylene-2,4-cyclohexadien-1-imine and related o-quinonoids by FVT of 1-hetero-1,2,3,4-tetrahydronaphthalenes". . p. 2013 - 2016. Retrieved 1991.
• 2、 Degner, Amanda,Carlsson, Henrik,Karlsson, Isabella,Eriksson, Johan,Pujari, Suresh S.,Tretyakova, Natalia Y.,T?rnqvist, Margareta. "Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood". . p. 1305 - 1314. Retrieved 2018/12/11.
• 3、 Menezes, José C. J. M. D. S.,Gomes, Ana T. P. C.,Silva, Artur M. S.,Faustino, Maria A. F.,Neves, Maria G. P. M. S.,Tomé, Augusto C.,De C. Da Silva, Fernando,Ferreira, Vitor F.,Cavaleiro, José A. S.. "Reaction of β-vinyl-meso-tetraphenylporphyrin with o-quinone methides". body text. p. 1841 - 1844. Retrieved 2011/10/01.