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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Structure
CAS No.
84-58-2
Chemical Name:
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Synonyms
2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE;4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile;Dichlorodicyanobenzoquinone;2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE;2,3-DICHLORO-5,6-DICYANOBENZOQUINONE;1,2-Dichloro-4,5-Dicyanobenzoquinone;Dichlorodicyanoquinone;2，3-Dicyano-5，6-dichlorobenzoquinone;2,3-dichloro-5,6-dicyano-4-benzoquinone;2,3,5,6-Dichlorodicyanoquinone
CBNumber:
CB5751792
Molecular Formula:
C8Cl2N2O2
Molecular Weight:
227
MOL File:
84-58-2.mol
MSDS File:
SDS
Modify Date:
2023/11/16 9:24:38
Request For Quotation

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Properties

Melting point 210-215 °C (dec.)(lit.)
Boiling point 301.8±42.0 °C(Predicted)
Density 1.7500 (estimate)
storage temp. 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 14,3063
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)
EPA Substance Registry System 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- (84-58-2)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  T
Risk Statements  25-29-41-37/38-20/21-23/24/25
Safety Statements  22-24/25-37-45-36/37-26-36/37/39
RIDADR  UN 3439 6.1/PG 3
WGK Germany  3
RTECS  GU4825000
F  21
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29269095
NFPA 704
1
3 2
W

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 250MG ₹1342.3 2022-06-14 Buy
Sigma-Aldrich(India) D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 5G ₹2143.35 2022-06-14 Buy
Sigma-Aldrich(India) D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 10G ₹2800 2022-06-14 Buy
Sigma-Aldrich(India) D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 100G ₹16730 2022-06-14 Buy
TCI Chemicals (India) D1070 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 84-58-2 25G ₹4100 2022-05-26 Buy
Product number Packaging Price Buy
D60400 250MG ₹1342.3 Buy
D60400 5G ₹2143.35 Buy
D60400 10G ₹2800 Buy
D60400 100G ₹16730 Buy
D1070 25G ₹4100 Buy

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Chemical Properties,Uses,Production

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.
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

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

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.

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.

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Preparation Products And Raw materials

Raw materials

Carbon tetrachloride 3,6-Dihydroxyphthalonitrile

Preparation Products

1-Benzofuran-5-carbaldehyde 2,6-Di-tert-butyl-p-benzoquinone 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran N-methylacridine 9-Methylene-9H-fluorene
2,7-Dibromophenanthrene 4-Methyl-3-nitrobenzonitrile
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Suppliers

Global( 498)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
Otto Chemie Pvt. Ltd. +91 9820041841 Mumbai, India 32 58 Inquiry
JSK Chemicals +919879767970 Gujarat, India 3756 58 Inquiry
TCI Chemicals (India) Pvt. Ltd. 1800 425 7889 New Delhi, India 6778 58 Inquiry
Otto Chemie Pvt. Ltd. +91 9820041841 Mumbai, India 5873 58 Inquiry
Alfa Aesar 1 800 209 7001 Maharashtra, India 6913 58 Inquiry
Central Drug House(P) Ltd. 91-11-49404040 New Delhi, India 6160 58 Inquiry
Triveni chemicals 08048762458 New Delhi, India 6093 58 Inquiry
LOBA CHEMIE PVT.LTD. 91-22-6663 6699 Mumbai, India 3077 58 Inquiry
Aarohi Enterprises 08047621208 Hyderabad, India 20 58 Inquiry
Sakshi Corporation 07942539673 Mumbai, India 223 58 Inquiry
Supplier Advantage
Otto Chemie Pvt. Ltd. 58
JSK Chemicals 58
TCI Chemicals (India) Pvt. Ltd. 58
Otto Chemie Pvt. Ltd. 58
Alfa Aesar 58
Central Drug House(P) Ltd. 58
Triveni chemicals 58
LOBA CHEMIE PVT.LTD. 58
Aarohi Enterprises 58
Sakshi Corporation 58

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2,3-Dichloro-5,6-dicyano-para-benzoquinone 2-dicarbonitrile,4,5-dichloro-3,6-dioxo-4-cyclohexadiene-1 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo- 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ ) 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE ( DDQ ) 99 DICHLORO(2,3-)-5,6-DICYANO-4-BENZOQUINONE LABOTEST-BB LT00005588 1,2-DICARBONITRILE-4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE 2,3-DICHLORO-5,6-DICYANOQUINONE 4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-CARBONITRILE 4,5-DICHLORO-3,6-DIOXO-1,4-CYCLOHEXADIENE-1,2-DICARBONITRILE 2,3-Dichloro-5,6-dicyano-1,4-Benzoquinone(DDQ) 4,5-dichloro-3,6-dihydroxy phthalonitrile 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINON 2,3-Dichloro-5,6-dicyanobenzoquinone, 98+% 2,3-Dichloro-5,6-dicyanobenzoq 1,2-Dichloro-4,5-dicyano-p-benzoquinone 2,3-Chloro-5,6-dicyanoquinone 2,3-Dichloro-5,6-dicyano-p-quinone 2,3-Dicyano-5,6-dichloro-2,5-cyclohexadiene-1,4-dione 3,6-Dihydro-3,6-dioxo-4,5-dichloro-1,2-benzenedicarbonitrile 4,5-Dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile DDQ(0-6℃) 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone,98% 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE pure 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ 3-Dichloro-5 4-benzoquinone (DDQ) 6-dicyano-1 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98% 100GR 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98% 10GR 4-Cyclohexadiene-1,2-dicarbonitrile,4,5-dichloro-3,6-dioxo-1 2,3-Dichloro-5,6-dicyano-p-benzoquinone,4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ 2,3-Dichloro-5,6-dic 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 1,2-Dichloro-4,5-dicyano-3,6-dioxocyclohexa-1,4-diene Two-5,6- two2,3-chlorinecyanogenp-benzoquinone 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% DDQ 2 3- two 6- two -5 chlorine cyanide, p-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 2,3-Dichloro-5,6-dicyano-p-benzoquinone, 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile 2,3-DichL oro-5,6-dicyano-1,4-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone > 2,3-Dichoro-5,6-dicyano-1,4-benzoquinone 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone ISO 9001：2015 REACH Dichloro-5,6-Dicyano-1,4-Benzoquinone(DDQ) 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) pure, 98% 2,3-DICHLORO-5,6-DICYANO-p-BENZOQUINONE For Synthesis 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-1,4-BENZOQUINONE 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE 2，3-Dicyano-5，6-dichlorobenzoquinone 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Dichlorodicyanobenzoquinone Dichlorodicyano-p-benzoquinone