|
| Product Name: | DDQ | | Synonyms: | 1,2-Dichloro-4,5-Dicyanobenzoquinone;2,3,5,6-Dichlorodicyanoquinone;2,3-dichloro-5,6-dicyano-4-benzoquinone;2,3-Dichloro-5,6-dicyano-para-benzoquinone;2-dicarbonitrile,4,5-dichloro-3,6-dioxo-4-cyclohexadiene-1;1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-;2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ );2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ ) 99 | | CAS: | 84-58-2 | | MF: | C8Cl2N2O2 | | MW: | 227 | | EINECS: | 201-542-2 | | Product Categories: | API intermediates;Benzoquinones;Benzoquinones, etc. (Charge Transfer Complexes);Biochemistry;Charge Transfer Complexes for Organic Metals;Functional Materials;Reagents for Oligosaccharide Synthesis;Aromatics;Intermediates | | Mol File: | 84-58-2.mol |  |
| Melting point | 210-215 °C (dec.)(lit.) | | Boiling point | 301.8±42.0 °C(Predicted) | | density | 1.7500 (estimate) | | storage temp. | Store below +30°C. | | solubility | Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane. | | form | Crystalline Powder or Crystals | | color | Yellow to orange | | Water Solubility | reacts | | Sensitive | Moisture Sensitive | | Merck | 14,3063 | | BRN | 747939 | | InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N | | CAS DataBase Reference | 84-58-2(CAS DataBase Reference) | | NIST Chemistry Reference | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2) | | EPA Substance Registry System | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2) |
| Description | 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has a variety of applications. DDQ is a deprotection agent for ketals, acetals, and thioacetals. It is a useful electron transfer reagent for synthesis of quinolones and an oxidizing agent used to synthesize steroids. Additionally, DDQ is used with Ph3P to synthesize 1,2-benzisoxazoles. | | Chemical Properties | yellow to orange powder | | Uses | An oxidizing agent, especially in steroid synthesis.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes. | | Application | 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
An effective reagent for the benzylic and allylic C?H functionalization.
An oxidizing agent for the synthesis of functionalized furans and benzofurans.
A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles. | | Preparation | The first synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) was described by J.Thiele and F.Guntber in 1906. However, no interest was shown in the compound until Linstead and co-workers discovered its extraordinary potency as a dehydrogenating agent. Its oxidation potential is greater than that of any other known quinone.
2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation | | Safety | DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). A low-temperature and weakly acidic environment increases the stability of DDQ. | | Purification Methods | Crystallise DDQ from CHCl3, CHCl3/*benzene (4:1), or *benzene and store it at 0o. [Pataki & Harvey J Org Chem 52 2226 1987, Beilstein 10 H 902, 10 II 635, 10 IV 3521.] |
| | DDQ Preparation Products And Raw materials |
|
