p-Benzoquinone, 98+%, Thermo Scientific Chemicals

Description

p-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
p-Benzoquinone is used as a dienophile in Diels-Alder cycloadditions to prepare naphthoquinones and 1,4-phenanthrenediones. It acts as a dehydrogenation reagent and an oxidizer in synthetic organic chemistry. In the Thiele-Winter reaction, it is involved in the preparation of triacetate of hydroxyquinol by reacting with acetic anhydride and sulfuric acid. It is also used in the synthesis of bromadol and to suppress double- bond migration during olefin metathesis reactions. It is used as a precursor to hydroquinone which finds application in photography and as a reducing agent and an antioxidant in rubber production.

Solubility
Soluble in water, ethanol, ether, methanol, benzene, acetone and ethyl acetate.

Notes
Light sensitive. Store in cool place. Incompatible and reacts violently with strong oxidizing agents.

Specifications

Chemical Identifiers

• CAS: 106-51-4
• Molecular Formula: C6H4O2
• Molecular Weight (g/mol): 108.096
• MDL Number: MFCD00001591
• InChI Key: AZQWKYJCGOJGHM-UHFFFAOYSA-N
• Synonym: p-benzoquinone, benzoquinone, quinone, 1,4-benzoquinone, p-quinone, chinone, 2,5-cyclohexadiene-1,4-dione, cyclohexadienedione, para-quinone, 1,4-benzoquine
• PubChem CID: 4650
• ChEBI: CHEBI:16509
• IUPAC Name: cyclohexa-2,5-diene-1,4-dione
• SMILES: C1=CC(=O)C=CC1=O

• Melting Point: 112°C to 115°C
• Density: 1.318
• Boiling Point: ∼180°C (sublimation)
• Flash Point: 77°C (171°F)
• Assay Percent Range: ≥98%
• Odor: Pungent
• Quantity: 100 g
• UN Number: UN2587
• Beilstein: 773967
• Sensitivity: Light sensitive
• Merck Index: 14,8074
• Solubility Information: Soluble in water,ethanol,ether,methanol,benzene,acetone and ethyl acetate.
• Formula Weight: 108.1
• Percent Purity: ≥98%
• Chemical Name or Material: p-Benzoquinone

Safety and Handling

Product Identifier

• p-Benzoquinone

Signal Word

• Danger

Hazard Category

• Acute toxicity Category 3
• ACUTE AQUATIC Acute 1
• Serious eye damage/eye irritation Category 2
• Skin corrosion/irritation Category 2
• Specific target organ toxicity Category 3

Hazard Statement

• H301-Toxic if swallowed.
• H315-Causes skin irritation.
• H319-Causes serious eye irritation.
• H331-Toxic if inhaled.
• H335-May cause respiratory irritation.
• H400-Very toxic to aquatic life.

Precautionary Statement

• P261-Avoid breathing dust/fume/gas/mist/vapours/spray.
• P273-Avoid release to the environment.
• P280-Wear protective gloves/protective clothing/eye protection/face protection.
• P302+P352-IF ON SKIN: Wash with plenty of water/soap.
• P304+P340-IF INHALED: Remove person to fresh air and keep comfortable for breathing.
• P305+P351+P338-IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

Supplemental information

• MIXTURE LIST-Contains : Quinone

RUO – Research Use Only