4,5-Dichlor-3,6-dioxocyclohexa-1,4-dien-1,2-dicarbonitril
DDQ · 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE · 2,3-dicyano-5,6-dichloro-p-benzoquinone · 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile · 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE · 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE · Dichlorodicyanobenzoquinone · 1,2-Dichloro-4,5-Dicyanobenzoquinone
Identifikatoren & physikalische Daten
| CAS No. | 84-58-2 |
|---|---|
| Summenformel | C8Cl2N2O2 |
| Durchschnittliche Molmasse | 227 g/mol |
| Monoisotopische Masse | 225,9336826 g/mol |
| SMILES | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O |
| InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N |
| PubChem CID | 6775 |
| ChEMBL | CHEMBL3759231 |
| EC No. | 201-542-2 |
| DTXSID | DTXSID7052577 |
| Lokaler Name | 4,5-Dichlor-3,6-dioxocyclohexa-1,4-dien-1,2-dicarbonitril |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 81,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 464 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| Physical Description | Yellow to orange solid[Merck Index] Dark yellow powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 210-215 °C (dec.)(lit.) |
| Siedepunkt | 301.8±42.0 °C(Predicted) |
| Dichte | 1.7500 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane.reacts |
| Aggregatzustand | Crystalline Powder or Crystals |
| Farbe | Yellow to orange |
| Merck | 14,3063 |
| BRN | 747939 |
| InChI | 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13 |
| InChIKey | HZNVUJQVZSTENZ-UHFFFAOYSA-N |
| SMILES | ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O |
| CAS Datenbank | 84-58-2(CAS DataBase Reference) |
| NIST chemische Informationen | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2) |
| EPA chemische Informationen | 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 77 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-Status: Active Update: 01-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/213372,3-Dichloro-5,6-dicyano-p-benzoquinone: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Intraperitoneal LD50 (mouse) = 31 mg/kgIntravenous LD50 (mouse) = 13 mg/kg[RTECS] Decomposed by water[Merck Index] Reacts with water evolving toxic gasesAn irritantToxic by ingestion[Alfa Aesar MSDS] See Hydroquinone. See NITRILES. |
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| F | 21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3439 6.1/PG 3 |
| Zollcode | 29269095 |
| RTECS-Nr. | GU4825000 |
| R-Sätze (R) | 25-29-41-37/38-20/21-23/24/25 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 22-24/25-37-45-36/37-26-36/37/39 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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