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

• ChemBase ID: 53625
• Molecular Formular: C6Cl4O2
• Molecular Mass: 245.875
• Monoisotopic Mass: 243.86523996
• SMILES: C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl
• Canonical SMILES: ClC1=C(Cl)C(=O)C(=C(C1=O)Cl)Cl
• InChI: InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
• InChIKey: UGNWTBMOAKPKBL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrachlorocyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: chloranil
• Synonyms: 2,3,5,6-Tetrachlorobenzo-1,4-quinone; 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione; CHLORANIL, PRACT; 2,3,5,6-Tetrachloro-1,4-benzoquinone; Chloranil; Tetrachloro-1,4-benzoquinone; Tetrachloro-p-benzoquinone; Chloranil; Chloranil; 3,4,5,6-Tetrachloro-p-benzoquinone; Tetrachloro-p-benzoquinone; p-CHLORANIL; 2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione; p-Chloranil; Tetrachloro-1,4-benzoquinone; p-Chloranil; 2,3,5,6-四氯-1,4-苯醌; 四氯对醌; 四氯苯醌; 四氯-1,4-苯醌; 四氯对苯醌; 四氯苯醌; 对四氯苯醌

Database IDs

• CAS Number: 118-75-2
• EC Number: 204-274-4
• MDL Number: MFCD00001594
• Beilstein Number: 393006
• Merck Index: 142078
• PubChem SID: 24899123; 24853870; 162058388; 24868849
• PubChem CID: 8371
• CHEBI ID: 36703
• CHEMBL: 192627
• Chemspider ID: 8068
• KEGG ID: C18933
• Unique Ingredient Identifier: 01W5X7N5XV
• Wikipedia Title: Chloranil

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.5799232
• LogD (pH = 7.4): 2.5799232
• Log P: 2.5799232
• Molar Refractivity: 50.194 cm^3
• Polarizability: 18.526142 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: yellow solid
• Melting Point: ~295 °C (dec.); 287-290°C; 289 - 291°C; 289 °C (dec.)(lit.); 289°C (decomposes); 295-296 °C (dec.); 295–296 °C; ca 290°C subl.
• Flash Point: >100°C
• Density: 1.97; 1.970
• Vapor Pressure: 5.1 x 10-6 mm Hg at 25 °C
• Hydrophobicity(logP): 3.3

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Light Sensitive; IRRITANT
• RTECS: DK6825000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077; UN3077
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3; III
• Risk Statements: 36/38-50/53; R:36/38-50/53; R36/38 R50/53
• Safety Statements: 37-60-61; S:37-60-61; S37 S60 S61
• TSCA Listed: false; 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H410; H400-H410-H315-H319-H303
• GHS Precautionary statements: P273-P305 + P351 + P338-P501; P280-P305+P351+P338-P302+P352-P321-P362-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Pharmacology Properties

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

Product Information

• Purity: ≥97.0% (AT); ≥99.0% (AT); 95%; 97%; 99%
• Grade: analytical standard; PESTANAL®, analytical standard; puriss.; purum
• Packaging: ampule of 1000 mg
• Sublimation Residue: ≤1%; ≤3%
• Linear Formula: C6Cl4(=O)2
• Empirical Formula (Hill Notation): C6Cl4O2

DETAILS

MP Biomedicals - 05208238

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156771

(3,4,5,6-Tetrachloro-p-benzoquinone; Tetrachloro-p-benzoquinone)

Sigma Aldrich - 45374

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 232017

Packaging
25, 100 g in poly bottle
Application
Synthesis of dibenzofurans via oxidative cyclization.1
Undergoes photoinduced cycloaddition reactions with stilbene derivatives and α,β-unsaturated carbonyl compounds. Fluorescence quencher.

Sigma Aldrich - 23280

Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds1

REFERENCES

• High potential quinones dehydrogenate many hydroaromatic systems by hydride abstraction.
• Reviews: Adv. Org. Chem., 2, 329 (1960); Chem. Rev., 67, 153 (1967); 78, 317 (1978).
• Forms complexes with many non-aromatic electron-donors, e.g. carbonyl compounds, esters, amides, lactones, lactams and alkyl iodides: J. Org. Chem., 53, 2163 (1988).