D60400
2,3-Dichloro-5,6-dicyano-p-benzoquinone
98%
Synonym(s):
4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ
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About This Item
Empirical Formula (Hill Notation):
C8Cl2N2O2
CAS Number:
Molecular Weight:
227.00
UNSPSC Code:
12352117
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-542-2
Beilstein/REAXYS Number:
747939
MDL number:
Assay:
98%
Form:
powder
Quality Level
assay
98%
form
powder
reaction suitability
reagent type: oxidant
mp
210-215 °C (dec.) (lit.)
storage temp.
2-8°C
SMILES string
ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O
InChI
1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
InChI key
HZNVUJQVZSTENZ-UHFFFAOYSA-N
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.
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
supp_hazards
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Regulatory Information
危险化学品
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DDQ-mediated formation of carbon? carbon bonds: Oxidation of imines
Bortolotti B, et al.
Tetrahedron, 49, 10157-10157 (1993)
Predictive model for oxidative C-H bond functionalization reactivity with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone.
Morales-Rivera CA, et al.
Journal of the American Chemical Society, 139(49), 17935-17944 (2017)
Mild and efficient photochemical and thermal deprotection of thioacetals and ketals using DDQ
Mathew L and Sankararaman S
The Journal of Organic Chemistry, 58, 7576-7576 (1993)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D60400-250MG | 04061833261453 |
| D60400-10G | 04061835556564 |
| D60400-100G | 04061833587195 |
| D60400-5G | 04061833587201 |