cyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 103047
• Molecular Formular: C6H4O2
• Molecular Mass: 108.09476
• Monoisotopic Mass: 108.02112937
• SMILES: O=C1C=CC(=O)C=C1
• Canonical SMILES: O=C1C=CC(=O)C=C1
• InChI: InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4H
• InChIKey: AZQWKYJCGOJGHM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: quinone
• Synonyms: p-benzoquinone; p-quinone; 1,4-Benzoquinone; benzoquinone; Quinone; p-BENZOQUINONE; p-Benzoquinone; 1,4-Benzoquinone; p-Benzoquinone; 苯醌; 对苯醌

Database IDs

• CAS Number: 106-51-4
• EC Number: 203-405-2
• MDL Number: MFCD00001591
• Beilstein Number: 773967
• Merck Index: 148074
• PubChem SID: 24847521; 24891552; 162090615
• PubChem CID: 4650
• CHEBI ID: 16509
• CHEMBL: 8320
• Chemspider ID: 4489
• KEGG ID: C00472
• Unique Ingredient Identifier: 3T006GV98U
• Wikipedia Title: 1,4-Benzoquinone

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0241138
• LogD (pH = 7.4): 1.0241138
• Log P: 1.0241138
• Molar Refractivity: 31.0288 cm^3
• Polarizability: 10.729253 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Slightly soluble in petroleum ether; soluble in acetone; very soluble in ethanol, benzene, diethyl ether; Slightly soluble in water
• Apperance: Yellow solid
• Melting Point: 111-114 °C; 112-114 °C; 112-115°C; 113-115 °C(lit.); 115°C; 116 °C
• Boiling Point: ca 180°C subl.; Sublimes
• Flash Point: 170.6 °F; 77 °C; 77°C(171°F)
• Auto Ignition Point: 560 °C (1040 °F); 815 °F
• Density: 1.3 (water = 1); 1.318; 1.318 g/cm^3 at 20 °C
• Vapor Pressure: 0.09 mm Hg at 20 °C; 0.1 mmHg ( 25 °C)
• Vapor Density: 3.7 (air = 1); 3.73 (vs air)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: DK2625000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2587; UN2587
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2Z
• Risk Statements: 23/25-36/37/38-50; R:23/25-36/37/38-50; R23/25 R36/37/38 R50
• Safety Statements: 26-28-45-61; S:26-28-45-61; S26 S28 S45 S61
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS09
• GHS Signal Word: Danger
• Main Hazard: Toxic
• GHS Hazard statements: H301 + H331-H315-H319-H335-H400; H301-H315-H319-H331-H335-H400; H301-H331-H315-H319-H335-H400
• GHS Precautionary statements: P261-P273-P301 + P310-P305 + P351 + P338-P311; P280H-P273-P305+P351+P338-P302+P352-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2587 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ACHE(43), BCHE(590), CES1(1066)

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); ≥99% (GC); ≥99.5% (HPLC); 95+%; 97%; 98%; 98+%
• Grade: purum; reagent grade
• Ignition Residue: ≤0.3% (as SO4)
• Quality: for spectrophotometric det. of amines
• Sublimation Residue: ≤0.1%; ≤1%
• Pharmacopeia Traceability: traceable to USP 1056504
• Linear Formula: C6H4(=O)2
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02150439

Purity: 98%

Sigma Aldrich - 12309

Other Notes
Reagent for the spectrophotometric microdetermination of amines1

Sigma Aldrich - B10358

General description
Free radical inhibitor
Packaging
1 kg in glass bottle
5, 100, 500 g in glass bottle
Application
Dienophile employed in Diels-Alder cycloadditions to form naphthoquinones,1 and 1,4-phenanthrenediones.2

REFERENCES

• Mild reoxidant in palladium-catalyzed reactions, to convert Pd(0) back to Pd(II); see e.g.: Org. Synth. Coll., 8, 137 (1993). For use in the Pd-catalyzed oxidative addition of amines to electron-deficient alkenes, to give enamines, see Palladium(II) chloride, 11034. For the cis-1,4-stereo- and regioselective chloroacetoxylation of 1,3-dienes by Pd(OAc)₂ and LiCl, in the presence of benzoquinone, see Palladium(II) acetate, 10516.
• Reacts with allyl or isoprenyl tin derivatives in the presence of BF₃ etherate to give ortho allyl-substituted quinones: Org. Synth. Coll., 9, 741 (1998). For a reaction scheme, see 2,3-Dimethoxy-5-methyl-1,4-benzoquinone, B24777.