CAS 84-58-2 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

NAVIGATION

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

PRICE INQUIRY

Catalog Number

ACM84582

CAS Number

84-58-2

Product Name

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Structure

Category

Charge Transfer Complexes; Molecular Conductors

IUPAC Name

4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile

Molecular Weight

227g/mol

Molecular Formula

C8Cl2N2O2

Canonical SMILES

C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N

InChI

InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13

InChI Key

HZNVUJQVZSTENZ-UHFFFAOYSA-N

Application

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) is an important chemical reagent with various applications in organic synthesis. It primarily functions as a powerful oxidizing agent, especially effective in the synthesis of steroids. DDQ is widely utilized as a deprotection agent for ketals, acetals, and thioacetals, and serves as a valuable electron-transfer reagent for producing quinolines from imines and alkynes or alkenes. In addition, it plays a crucial role in oxidative couplings, cyclization reactions, and the dehydrogenation of alcohols, phenols, and steroid ketones. Furthermore, DDQ is used in conjunction with Ph3P to efficiently synthesize 1,2-benzisoxazoles, as well as in the functionalization of benzylic and allylic C-H bonds, contributing to the creation of functionalized furans and benzofurans. Its versatile nature makes DDQ indispensable in modern synthetic chemistry.

Complexity

464

Covalently-Bonded Unit Count

EC Number

201-542-2

Exact Mass

225.933683g/mol

Formal Charge

Heavy Atom Count

MeSH Entry Terms

2,3-DDQ;2,3-dichloro-5,6-dicyano-1,4-benzoquinone;2,3-dichloro-5,6-dicyanobenzoquinone;dichlorodicyanobenzoquinone

Monoisotopic Mass