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ChemicalBook >> CAS DataBase List >>2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

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

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Structure
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
MDL Number:
MFCD00001593
MOL File:
84-58-2.mol
MSDS File:
SDS
Last updated:2023-11-16 09:24:38
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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)
EWG's Food Scores 1
FDA UNII 1H5KD39UH7
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)  GHS hazard pictograms
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(50)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 5g $30 2024-03-01 Buy
Sigma-Aldrich D60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone 98% 84-58-2 10g $53.6 2024-03-01 Buy
TCI Chemical D1070 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) 84-58-2 25g $104 2024-03-01 Buy
TCI Chemical D1070 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 84-58-2 5G $30 2021-12-16 Buy
TCI Chemical D1070 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone >97.0%(T) 84-58-2 250g $632 2024-03-01 Buy
Product number Packaging Price Buy
D60400 5g $30 Buy
D60400 10g $53.6 Buy
D1070 25g $104 Buy
D1070 5G $30 Buy
D1070 250g $632 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 synthesis

1425681-45-3
106266-06-2
84-58-2
Synthesis of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone from 1,4-Cyclohexadiene-1,2-dicarbonitrile, 4,5-dichloro-3,6-dioxo-, compd. with 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (1:1)

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( 501)Suppliers
Supplier Tel Email Country ProdList Advantage
Hangzhou Qiwei Pharmatech Co.,Ltd
13282840061 mw@qwpharmatech.com China 109 58
Hebei Yanxi Chemical Co., Ltd. 		+8617531190177 peter@yan-xi.com China 5993 58
Firsky International Trade (Wuhan) Co., Ltd 		+8615387054039 admin@firsky-cn.com China 436 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21695 55
Zjartschem 		+86-571-8723 8903 jocelynpan@zjarts.com jocelynpan@zjarts.com CHINA 993 58
Tianjin Zhongxin Chemtech Co., Ltd. 		+86-022-66880623 +8618622897568 sales@tjzxchem.com China 559 58
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
NINGBO INNO PHARMCHEM CO., LTD. 		13867897135 sales@nbinno.com CHINA 925 58
Hubei Jusheng Technology Co.,Ltd. 		18871490254 linda@hubeijusheng.com CHINA 28180 58
Supplier Advantage
Hangzhou Qiwei Pharmatech Co.,Ltd
58
Hebei Yanxi Chemical Co., Ltd. 		58
Firsky International Trade (Wuhan) Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Zjartschem 		58
Tianjin Zhongxin Chemtech Co., Ltd. 		58
career henan chemical co 		58
NINGBO INNO PHARMCHEM CO., LTD. 		58
Hubei Jusheng Technology Co.,Ltd. 		58

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View Lastest Price from 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone pictures 2024-04-19 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
 US $0.00 / Kg/Drum 1KG 99% 200mt/year Jinan Finer Chemical Co., Ltd
DDQ pictures 2023-10-23 DDQ
84-58-2
 US $0.00 / kg 1kg 99 20tons Hebei Yanxi Chemical Co., Ltd.
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone pictures 2023-10-08 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
84-58-2
 US $30.00 / KG 1KG 99% 20T Firsky International Trade (Wuhan) Co., Ltd
  • DDQ pictures
  • DDQ
    84-58-2
  • US $0.00 / kg
  • 99
  • Hebei Yanxi Chemical Co., Ltd.

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

DDQ(84-58-2)MSDDQ(84-58-2)13CNMRDDQ(84-58-2)IR1DDQ(84-58-2)IR2DDQ(84-58-2)Raman

84-58-2(2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)Related Search:

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CIS-1,2-DICHLOROETHYLENE 2-Chloropropene 4-Chlorobutyronitrile Chloroacetone hex-2-enal
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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