| Identification | More | [Name]
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone | [CAS]
84-58-2 | [Synonyms]
1,2-DICARBONITRILE-4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE
2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE
2,3-DICHLORO-5,6-DICYANOBENZOQUINONE
2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE
2,3-DICHLORO-5,6-DICYANOQUINONE
2，3-Dicyano-5，6-dichlorobenzoquinone
4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-CARBONITRILE
4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-DICARBONITRILE
DDQ
DICHLORO(2,3-)-5,6-DICYANO-4-BENZOQUINONE
LABOTEST-BB LT00005588
1,2-Dichloro-4,5-Dicyanobenzoquinone
2,3,5,6-Dichlorodicyanoquinone
2,3-dichloro-5,6-dicyano-4-benzoquinone
2,3-Dichloro-5,6-dicyano-para-benzoquinone
2-dicarbonitrile,4,5-dichloro-3,6-dioxo-4-cyclohexadiene-1
4-Cyclohexadiene-1,2-dicarbonitrile,4,5-dichloro-3,6-dioxo-1
Dichlorodicyanobenzoquinone
Dichlorodicyano-p-benzoquinone
Dichlorodicyanoquinone | [EINECS(EC#)]
201-542-2 | [Molecular Formula]
C8Cl2N2O2 | [MDL Number]
MFCD00001593 | [Molecular Weight]
227 | [MOL File]
84-58-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to orange powder | [Melting point ]
210-215 °C (dec.)(lit.)
| [Boiling point ]
301.8±42.0 °C(Predicted) | [density ]
1.7500 (estimate) | [storage temp. ]
0-6°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 | [Detection Methods]
HPLC | [Merck ]
14,3063 | [BRN ]
747939 | [InChIKey]
HZNVUJQVZSTENZ-UHFFFAOYSA-N | [CAS DataBase Reference]
84-58-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-(84-58-2) | [Storage Precautions]
Moisture sensitive | [EPA Substance Registry System]
84-58-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R25:Toxic if swallowed.
R29:Contact with water liberates toxic gas.
R41:Risk of serious damage to eyes.
R37/38:Irritating to respiratory system and skin .
R20/21:Harmful by inhalation and in contact with skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37:Wear suitable gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3439 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
GU4825000
| [F ]
21 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29269095 |
| Hazard Information | Back Directory | [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. | [Chemical Properties]
yellow to orange powder | [Uses]
An oxidizing agent, especially in steroid synthesis. | [Application]
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
An effective reagent for the benzylic and allylic C?H functionalization.
An oxidizing agent for the synthesis of functionalized furans and benzofurans.
A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles. | [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 | [Mechanism of action]
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) has many applications in the oxidation of various organic compounds such as ketones, alcohols, phenols, aromatic compounds, heterocyclic structures, etc. Apart from that, the presence of two chlorine atoms and two nitrile groups on the benzoquinone ring may also behave as a potential chlorinating agent. Consequently, DDQ could act simultaneously as the chlorinating agent and the oxidant. It can also remove the protective functional groups during deprotections of different chemical entities. For dehydrogenation by DDQ, the mechanism includes the transfer of hydride to the quinone oxygen followed by the transfer of a proton to the phenolate ion[1]. | [Safety]
DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). A low-temperature and weakly acidic environment increases the stability of DDQ. | [Purification Methods]
Crystallise DDQ from CHCl3, CHCl3/*benzene (4:1), or *benzene and store it at 0o. [Pataki & Harvey J Org Chem 52 2226 1987, Beilstein 10 H 902, 10 II 635, 10 IV 3521.] | [References]
[1] Alsharif, Meshari A. et al. “DDQ as a versatile and easily recyclable oxidant: a systematic review.” RSC Advances 47 (2021): 29826–29858.
|
| Well-known Reagent Company Product Information | Back Directory | [Acros Organics]
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98%(84-58-2) | [Alfa Aesar]
2,3-Dichloro-5,6-dicyanobenzoquinone, 98+%(84-58-2) | [Sigma Aldrich]
84-58-2(sigmaaldrich) | [TCI AMERICA]
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone,>97.0%(T)(84-58-2) |
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