4,5-Dichlor-3,6-dioxocyclohexa-1,4-dien-1,2-dicarbonitril
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
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Grundinformationen
- CAS
84-58-2- Standard-SMILES
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O- InChIKey
HZNVUJQVZSTENZ-UHFFFAOYSA-N- Summenformel
- C8Cl2N2O2
- Durchschnittliche Molmasse
- 227 g/mol
- Monoisotopische Masse
- 225,9336826
Überblick
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Namen und Bezeichner
- Bevorzugter Name
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- IUPAC
- 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
- Lokaler Name
- 4,5-Dichlor-3,6-dioxocyclohexa-1,4-dien-1,2-dicarbonitril
- Englischer Name
- 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
- Summenformel
- C8Cl2N2O2
- Molmasse
- 227
Namen und Synonyme
84-58-22,3-Dichloro-5,6-dicyano-1,4-benzoquinoneDichlorodicyanobenzoquinone2,3-Dichloro-5,6-dicyano-p-benzoquinone2,3-Dichloro-5,6-dicyanobenzoquinoneDichlorodicyano-p-benzoquinone1,4-CYCLOHEXADIENE-1,2-DICARBONITRILE, 4,5-DICHLORO-3,6-DIOXO-2,3-Dichloro-5,6-dicyanoquinone4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile2,3-Dichloro-5,6-dicyano-p-quinone2,3-Dicyano-5,6-dichlorobenzoquinone2,3-Dicyano-5,6-dichloro-1,4-benzoquinone
Weitere Namen anzeigen
DDQ2,3-dicyano-5,6-dichloro-p-benzoquinone4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile1,2-Dichloro-4,5-Dicyanobenzoquinone2，3-Dicyano-5，6-dichlorobenzoquinone2,3-dichloro-5,6-dicyano-4-benzoquinone
5,6-Dichloro-2,3-dicyano-p-benzoquinone5,6-Dicyano-2,3-dichloro-p-benzoquinone1H5KD39UH7NSC-401087RefChem:1330572,3-DDQDTXCID10818133201-542-2
Datenbank-Bezeichner
- CAS
84-58-2- PubChem CID
- 6775
- DTXSID
DTXSID7052577- ChEMBL
CHEMBL3759231- UNII
- 1H5KD39UH7
- EC Number
- 201-542-2
- Nikkaji
- J4.898D、J510.000C
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 81,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 464
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physical DescriptionYellow to orange solid; [Merck Index] Dark yellow powder; [Alfa Aesar MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 210 · 210-215 °C (dec.)(lit.)
- Siedepunkt
- 301.8 · 301.8±42.0 °C(Predicted)
- Dichte
- 1.75 · 1.7500 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane.
- Aggregatzustand
- Crystalline Powder or Crystals
- Farbe
- Yellow to orange
- Wasserlöslichkeit
- reacts
- Merck
- 14 · 14,3063
- BRN
- 747939 · 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 · 84-58-2(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2)
- EPA chemische Informationen
- 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (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.
Gefahrenhinweise
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/21337
2,3-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/kg; Intravenous LD50 (mouse) = 13 mg/kg; [RTECS] Decomposed by water; [Merck Index] Reacts with water evolving toxic gases; An irritant; Toxic by ingestion; [Alfa Aesar MSDS] See Hydroquinone. See NITRILES.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Sicherheitsdaten
- F
- 21
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3439 6.1/PG 3
- hs_code
- 29269095
- RTECS-Nr.
- GU4825000
- risk_code
- 25-29-41-37/38-20/21-23/24/25
- hazard_code
- T
- safety_code
- 22-24/25-37-45-36/37-26-36/37/39
- hazard_class
- 6.1
- packing_group
- II
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 Oral
Chemie und Industrie
Verwendung und Herstellung
UsesUsed in steroid synthesis (oxidizing agent); [Merck Index]
General Manufacturing Information1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-: ACTIVE
Anwendungen
Beschreibung2,3-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.
VerwendenAn 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.
Darstellung
synthetischeThe 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
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