2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
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
Identifiers & Physical Properties
| CAS No. | 84-58-2 |
|---|---|
| Molecular formula | C8Cl2N2O2 |
| Average molar mass | 227 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 1.6 |
|---|---|
| Topological polar surface area | 81.7 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 0 |
| Heavy atoms | 14 |
| Formal charge | 0 |
| Complexity | 464 |
| Chemical classes | 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] |
| Melting point | 210-215 °C (dec.)(lit.) |
| Boiling point | 301.8±42.0 °C(Predicted) |
| Density | 1.7500 (estimate) |
| Storage conditions | Store below +30°C. |
| Solubility | Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane.reacts |
| Physical state | Crystalline Powder or Crystals |
| Color | Yellow to orange |
| Sensitivity | Moisture Sensitive |
| 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 DataBase Reference | 84-58-2(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 1H5KD39UH7 |
| 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) |
| UNSPSC Code | 12352117 |
| NACRES | NA.22 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301+H311+H331-H315-H319 |
| GHS precautionary statements | P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard symbols | T |
| Risk statements (R) | 25-29-41-37/38-20/21-23/24/25 |
| Safety statements (S) | 22-24/25-37-45-36/37-26-36/37/39 |
| UN transport number | UN 3439 6.1/PG 3 |
| Water hazard class (WGK) | 3 |
| RTECS number | GU4825000 |
| F | 21 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 Oral |
| Packing group | II |
| Customs code | 29269095 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | 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. |
|---|---|
| Regulatory information | 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 |
| Hazards summary | 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 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | GU4825000 |
| UN transport number | UN 3439 6.1/PG 3 |
| Customs code | 29269095 |
| Risk statements (R) | 25-29-41-37/38-20/21-23/24/25 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | T |
| Safety statements (S) | 22-24/25-37-45-36/37-26-36/37/39 |
| Hazard class | 6.1Acute Tox. 3 Oral |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | II |
| GHS hazard statements | H301+H311+H331-H315-H319 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 |
Applications & Uses
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.
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.
Preparation & Synthesis
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