2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (HCID 6775)

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 Struktureigenschaften

XLogP: 1,6
Polarare Oberfläche (TPSA): 81,7 Å²
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

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 3 Einträge

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 · 1 Eintrag

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 · 2 Einträge

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 · 1 Eintrag

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