B10358

p-Benzoquinone

reagent grade, ≥98%

• Synonym(s): Quinone
• Linear Formula: C₆H₄(=O)₂
• CAS Number: 106-51-4
• Molecular Weight: 108.09
• Beilstein: 773967
• EC Number: 203-405-2
• MDL number: MFCD00001591
• UNSPSC Code: 12352005
• PubChem Substance ID: 57653913
• NACRES: NA.21

Properties

• biological source: synthetic
• Quality Level: 200
• grade: reagent grade
• vapor density: 3.73 (vs air)
• vapor pressure: 0.1 mmHg ( 25 °C)
• Assay: ≥98%
• form: powder or crystals
• autoignition temp.: 815 °F
• greener alternative product characteristics: Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• mp: 113-115 °C (lit.)
• solubility: water: soluble 14.7 g/L at 20 °C
• functional group: ketone
• greener alternative category: Aligned
• storage temp.: room temp
• SMILES string: O=C1C=CC(=O)C=C1
• InChI: 1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
• InChI key: AZQWKYJCGOJGHM-UHFFFAOYSA-N
• Gene Information: human ... ACHE(43) , BCHE(590) , CES1(1066)

Description

General description

p-Benzoquinone (PBQ) is a cyclic conjugated diketone. Its high-resolution photoelectron spectrum has been reported.[1] The visible and near ultraviolet spectra of PBQ have been recorded and analyzed.[2] Its addition as coagent has been reported to enhance the crosslinking rate of polypropylene initiated by the pyrolysis of peroxides.[3] Its impact on hemoglobin (Hb) has been investigated based on immunoblots and mass spectral analysis of a smoker′s blood.[4]

Free radical inhibitor

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Application

p-Benzoquinone may be used to form benzofuranone derivatives on reacting with anilides of β-aminocrotonic acids via Nenitzescu reaction.[5]

Dienophile employed in Diels-Alder cycloadditions to form naphthoquinones,[6] and 1,4-phenanthrenediones.[7]

Oxidant used in first step of greener amine synthesis from terminal olefins by Wacker oxidation followed by transfer hydrogenation of the resultant imine.

Formal anti-Markovnikov hydroamination of terminal olefins

Safety Information

• Pictograms: GHS02,GHS06,GHS08,GHS05,GHS09
• Signal Word: Danger
• Hazard Statements: H228,H301 + H331,H314,H317,H335,H341,H410
• Precautionary Statements: P210 - P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Sol. 1 - Muta. 2 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 4.1B - Flammable solid hazardous materials
• WGK: WGK 3
• Flash Point(F): 170.6 °F - closed cup
• Flash Point(C): 77 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves