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

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

Product Name
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
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
Formula Weight
227
MOL File
84-58-2.mol
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D60400
Product name
2,3-Dichloro-5,6-dicyano-p-benzoquinone
Purity
98%
Packaging
5g
Price
$30
Updated
2024/03/01
Sigma-Aldrich
Product number
D60400
Product name
2,3-Dichloro-5,6-dicyano-p-benzoquinone
Purity
98%
Packaging
10g
Price
$53.6
Updated
2024/03/01
TCI Chemical
Product number
D1070
Product name
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Purity
>97.0%(T)
Packaging
25g
Price
$104
Updated
2024/03/01
TCI Chemical
Product number
D1070
Product name
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Packaging
5G
Price
$30
Updated
2021/12/16
TCI Chemical
Product number
D1070
Product name
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Purity
>97.0%(T)
Packaging
250g
Price
$632
Updated
2024/03/01
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Chemical Properties,Usage,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.

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.

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

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

Jinan Finer Chemical Co., Ltd
Product
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 84-58-2
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
200mt/year
Release date
2021-09-17
Hebei Yanxi Chemical Co., Ltd.
Product
DDQ 84-58-2
Price
US $0.00/kg
Min. Order
1kg
Purity
99
Supply Ability
20tons
Release date
2023-10-23
Great Innovation (Shanghai) Pharma Co., Ltd.,
Product
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 84-58-2
Price
US $10.00/Kg/Drum
Min. Order
500KG
Purity
99%
Supply Ability
10T per month
Release date
2021-07-28

84-58-2, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinoneRelated Search:

4,4'-Dichlorodiphenyl sulfone Chloranil Idebenone Diphenyldichloromethane 1,4-Benzoquinone 2,6-DICHLORO-1,4-BENZOQUINONE Titanocene dichloride Bis(cyclopentadienyl)zirconium dichloride 1,4-Benzoquinone dioxime Tetraacetylethylenediamine CIS-1,2-DICHLOROETHYLENE 2-Chloropropene 4-Chlorobutyronitrile Chloroacetone hex-2-enal 2-CHLORO-1,4-BENZOQUINONE 1-METHYL-1,4-CYCLOHEXADIENE HYDROGEN CYANIDE

  • 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
  • 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-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
  • 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-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
  • Dichlorodicyanobenzoquinone
  • Dichlorodicyano-p-benzoquinone
  • Dichlorodicyanoquinone
  • 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 &gt
  • 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%