1,2-Benzoquinone

Base Information

• Chemical Name: 1,2-Benzoquinone
• CAS No.: 583-63-1
• Deprecated CAS: 526209-93-8
• Molecular Formula: C6H4 O2
• Molecular Weight: 108.097
• European Community (EC) Number: 812-469-6
• UNII: SVD1LJ47R7
• DSSTox Substance ID: DTXSID60894765
• Nikkaji Number: J7.445D,J3.332.157K
• Wikipedia: 1,2-Benzoquinone,Orthobenzoquinone
• Wikidata: Q402601
• Metabolomics Workbench ID: 41855
• Mol file: 583-63-1.mol

Synonyms:1,2-benzoquinone;2-benzoquinone;o-benzoquinone

Chemical Property of 1,2-Benzoquinone

Chemical Property:

• Melting Point: 65°C (rough estimate)
• Refractive Index: 1.5017 (estimate)
• Boiling Point: 213.3°Cat760mmHg
• Flash Point: 76.4°C
• PSA: 34.14000
• Density: 1.256g/cm³
• LogP: 0.25060
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.021129366
• Heavy Atom Count: 8
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

1,2-BENZOQUINONE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: A poison. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C(=O)C=C1

Technology Process of 1,2-Benzoquinone

There total 59 articles about 1,2-Benzoquinone 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: 95.0%

1,2-diamino-benzene (95-54-5) → ortoquinone (583-63-1)

Guidance literature:

With sodium hypochlorite; Dowex 1X₈-200 - chloride form; In dichloromethane; for 2.5h;

DOI:10.1039/a905598c

Reference yield: 93.0%

2-methoxy-phenol (90-05-1) → ortoquinone (583-63-1)

Guidance literature:

With potassium hydroxide; lithium perchlorate; In water; acetonitrile; at 0 ℃; anodic oxidation at Pt electrode;

Reference yield: 91.0%

2-amino-phenol (95-55-6) → ortoquinone (583-63-1)

Guidance literature:

With sodium hypochlorite; Dowex 1X₈-200 - chloride form; In ethyl acetate; for 2.5h;

DOI:10.1039/a905598c

upstream raw materials:

1-Ethynylcyclohexan-1-ol

2-methoxy-phenol

phenol

benzo[1,4]dioxine

Downstream raw materials:

4-indol-3-yl-[1,2]benzoquinone

(E)-2-(phenyldiazenyl)phenyl benzoate

cis,cis-Muconic acid

4-chloro-1,2-benzenediol

Refernces

Triphenylphosphane-mediated addition of dimethyl acetylenedicarboxylate to 1,2- and 1,4-benzoquinones: Synthesis of novel γ-spirolactones

10.1055/s-2000-8212

The research investigates the addition of zwitterionic intermediates, generated by triphenylphosphane and dimethyl acetylenedicarboxylate (DMAD), to 1,2- and 1,4-benzoquinones to synthesize novel unsaturated ?-spirolactones. The purpose is to explore the reactivity of quinones towards these intermediates and develop a method for creating highly functionalized spirolactones. The study finds that both ortho- and para-quinones readily react with the zwitterionic intermediate, yielding spirolactones in moderate to high yields. Key chemicals used include triphenylphosphane, DMAD, various benzoquinones (such as 4,6-di-tert-butyl-3-methoxy-1,2-benzoquinone and 1,4-benzoquinone), and solvents like benzene. The results show that this method provides a facile route to produce spirolactones, which are present in several biologically active natural products.