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

Overview

request from searcher

Names & identifiers

Preferred name: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
IUPAC: 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
English name: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Molecular formula: C8Cl2N2O2
Molecular weight: 227

Names & synonyms

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

Show more names

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

Database identifiers

CAS: 84-58-2
PubChem CID: 6775
DTXSID: DTXSID7052577
ChEMBL: CHEMBL3759231
UNII: 1H5KD39UH7
EC Number: 201-542-2
Nikkaji: J4.898D、J510.000C

Properties

Computed structural properties

XLogP: 1.6
Topological polar surface area: 81.7 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 14
Formal charge: 0
Complexity: 464

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy

Physical DescriptionYellow to orange solid; [Merck Index] Dark yellow powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point: 210 · 210-215 °C (dec.)(lit.)
Boiling point: 301.8 · 301.8±42.0 °C(Predicted)
Density: 1.75 · 1.7500 (estimate)
storage temp.: 30 °C · 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 · 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 DataBase Reference: 84 · 84-58-2(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 1 H5KD39UH7 · 1H5KD39UH7
NIST Chemistry Reference: 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2)
EPA Substance Registry System: 1 · 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2)
UNSPSC Code: 12352117 · 12352117
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301+H311+H331-H315-H319
Precautionary statements: 501 · 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
PPE: 2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes: T
Risk Statements: 25 · 25-29-41-37/38-20/21-23/24/25
Safety Statements: 22 · 22-24/25-37-45-36/37-26-36/37/39
RIDADR: 3439 · UN 3439 6.1/PG 3
WGK Germany: 3 · 3
RTECS: 4825000 · GU4825000
F: 21 · 21
TSCA: TSCA listed
HazardClass: 6.1 · 6.1
PackingGroup: II
HS Code: 29269095 · 29269095
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 Oral · Acute Tox. 3 Oral
REACH Registrations: Active
Limited Quantities: 5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 3 items

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 item

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%)

Safety data

F: 21
PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 3
tsca: TSCA listed
rtecs: GU4825000
ridadr: UN 3439 6.1/PG 3
hs_code: 29269095
risk_code: 25-29-41-37/38-20/21-23/24/25
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T
safety_code: 22-24/25-37-45-36/37-26-36/37/39
hazard_class: 6.1
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: II
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
Hazard Classifications: Acute Tox. 3 Oral
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

Chemistry & industry

Uses & manufacturing

UsesUsed in steroid synthesis (oxidizing agent); [Merck Index]

General Manufacturing Information1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-: ACTIVE

Applications · 2 items

Description2,3-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.

UsesAn 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 methods · 1 item

PreparationThe 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