CAS 118-75-2|Tetrachloro-<i>p</i>-benzoquinone|2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione|Chloranil|Tetrachloro-p-benzoquinone|Chloranil|四氯苯醌|四氯对苯醌|2,3,5,6-Tetrachlorocyclohexa-2,5-di...

General Information

Structure

Molecular Formula

C₆Cl₄O₂

Molecular Mass

245.875

Exact Mass

243.86523996

Charge

InChI

InChI=1S/C6Cl4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11

InChIKey

UGNWTBMOAKPKBL-UHFFFAOYSA-N

Canonic Smiles

ClC1=C(Cl)C(=O)C(=C(C1=O)Cl)Cl

Isomeric Smiles

C1(=C(C(=O)C(=C(C1=O)Cl)Cl)Cl)Cl

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.5799232

LogD (pH = 7.4)

2.5799232

Log P

2.5799232

Molar Refractivity

50.194

Polarizability

18.526142

Polar Surface Area

34.14

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Chloranil2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dioneTetrachloro-p-benzoquinoneTetrachloro-p-benzoquinoneChloranil四氯对苯醌四氯苯醌Tetrachloro-1,4-benzoquinonep-Chloranil2,3,5,6-Tetrachlorocyclohexa-2,5-diene-1,4-dione2,3,5,6-Tetrachlorobenzo-1,4-quinonep-CHLORANIL3,4,5,6-Tetrachloro-p-benzoquinoneCHLORANIL, PRACT四氯苯醌Chloranil对四氯苯醌四氯对醌2,3,5,6-四氯-1,4-苯醌Tetrachloro-1,4-benzoquinone2,3,5,6-Tetrachloro-1,4-benzoquinone四氯-1,4-苯醌p-Chloranil

IUPAC Traditional name

chloranil

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem SID

162058388248538702489912324868849

PubChem CID

EC Number

CAS Number

Chemspider ID

MDL Number

CHEMBL

Unique Ingredient Identifier

Wikipedia Title

KEGG ID

Beilstein Number

CHEBI ID

Merck Index

Registration numbers

Properties

Pharmacology Properties

human ... ACHE(43), BCHE(590), CES1(1066)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02156771

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

05208238

MP Biomedicals Rare Chemical collection

Wikipedia

Chloranil

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.

23280

Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds1

45374

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• High potential quinones dehydrogenate many hydroaromatic systems by hydride abstraction.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

chloranil

IUPAC name

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

Registration numbers

PubChem SID

162058388248538702489912324868849

PubChem CID

EC Number

CAS Number

Chemspider ID

MDL Number

CHEMBL

Unique Ingredient Identifier

Wikipedia Title

KEGG ID

Beilstein Number

CHEBI ID

Merck Index

Molecule Details

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

05208238

MP Biomedicals Rare Chemical collection

Wikipedia

Chloranil

Sigma Aldrich

232017

23280

Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds1

45374

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

References

PubChem Literature

From Data Sources

• 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).

• High potential quinones dehydrogenate many hydroaromatic systems by hydride abstraction.

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

human ... ACHE(43), BCHE(590), CES1(1066)

Molecule

ID:53625