Hydrafacial When Can I Start Hydroquinone Again

"DDQ" redirects hither. For the Australian goggle box station, see RTQ.

2,3-Dichloro-5,6-dicyano-one,iv-benzoquinone^[i]

Names
Preferred IUPAC name 4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-i,2-dicarbonitrile[2]
Other names 2,3-Dichloro-5,half dozen-dicyano-p-benzoquinone iv,5-Dichloro-3,half-dozen-dioxo-1,iv-cyclohexadiene-1,ii-dicarbonitrile Dichlorodicyanobenzoquinone
Identifiers
CAS Number	84-58-2 Y
3D model (JSmol)	Interactive image
Abbreviations	DDQ
ChemSpider	6517 Y
ECHA InfoCard	100.001.402
EC Number	201-542-two
PubChem CID	6775
RTECS number	GU4825000
UNII	1H5KD39UH7 Y
CompTox Dashboard (EPA)	DTXSID7052577
InChI InChI=1S/C8Cl2N2O2/c9-5-6(10)eight(14)four(2-12)iii(1-xi)7(5)13 Y Key: HZNVUJQVZSTENZ-UHFFFAOYSA-Northward Y InChI=i/C8Cl2N2O2/c9-5-half dozen(ten)8(14)4(2-12)iii(1-11)vii(5)thirteen Key: HZNVUJQVZSTENZ-UHFFFAOYAL
SMILES ClC=1C(=O)C(\C#N)=C(\C#North)C(=O)C=1Cl
Properties
Chemic formula	C 8 Cl 2 North 2 O 2
Tooth mass	227.00 thousand·mol−ane
Appearance	yellow to orange powder
Density	1.7g/cm3
Melting point	210 to 215 °C (410 to 419 °F; 483 to 488 Yard) (decomposes)
Boiling point	301.8 °C (575.2 °F; 575.0 K) at 760mmHg
Solubility in water	reacts
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264, P270, P301+P310, P321, P330, P405, P501
Flash indicate	136.3 °C (277.3 °F; 409.iv G)
Except where otherwise noted, information are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yverify (what is Y N  ?)
Infobox references

Chemical compound

ii,3-Dichloro-v,6-dicyano-i,iv-benzoquinone (or DDQ) is the chemical reagent with formula C₆Cl₂(CN)₂O₂. This oxidant is useful for the dehydrogenation of alcohols,^[3] phenols,^[4] and steroid ketones.^[5] DDQ decomposes in h2o, but is stable in aqueous mineral acid.^[six]

Training [edit]

Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther starting time reported a 6-pace training in 1906.^[7] The substance did not receive interest until its potential as a dehydrogenation amanuensis was discovered. A single-pace chlorination from two,3-dicyanohydroquinone was reported in 1965.^[8]

Reactions [edit]

The reagent removes pairs of H atoms from organic molecules. The stoichiometry of its action is illustrated by the conversion of tetralin to naphthalene:

2 C₆Cl₂(CN)_iiO₂ + C₁₀H₁₂ → 2 C₆Cl₂(CN)₂(OH)_two + C₁₀H₈

The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which facilitates workup.

Solutions of DDQ in benzene are red, due to the formation of a charge-transfer complex.^[9]

Dehydrogenation [edit]

Aromatization [edit]

^[10]

Cross-Dehydrogenative Coupling [edit]

^[11]

Safety [edit]

DDQ reacts with h2o to release highly toxic hydrogen cyanide (HCN). A depression-temperature and weakly acidic environment increases the stability of DDQ.

References [edit]

1. ^ 2,3-Dichloro-five,6-dicyano-p-benzoquinone at Sigma-Aldrich
2. ^ Classification of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blueish Book). Cambridge: The Purple Guild of Chemistry. 2014. p. 50. doi:ten.1039/9781849733069-FP001. ISBN978-0-85404-182-iv.
3. ^ Braude, E. A.; Linstead, R. P.; Wooldridge, K. R. H. (1956). "593. Hydrogen Transfer. Function 9 The Selective Dehydrogenation of Unsaturated Alcohols by High-potential Quinones". Journal of the Chemical Society (Resumed). 1956: 3070–3074. doi:10.1039/JR9560003070.
4. ^ Becker, H. D. (1965). "Quinone Dehydrogenation. I. Oxidation of Monohydric Phenols". Journal of Organic Chemistry. 30 (4): 982–989. doi:10.1021/jo01015a006.
5. ^ Turner, A. B.; Ringold, H. J. (1967). "Applications of High-potential Quinones. Part I. The Machinery of Dehydrogenation of Steroidal Ketones by 2,3-Dichloro-5,half-dozen-Dicyanobenzoquinone". Journal of the Chemical Society C: Organic. 1967: 1720–1730. doi:10.1039/J39670001720.
6. ^ Derek R. Buckle, Steven J. Collier, Marking D. McLaws "2,3-Dichloro-v,6-dicyano-1,four-benzoquinone" in E-EROS ENCYCLOPEDIA OF REAGENTS FOR ORGANIC SYNTHESIS, 2005. doi:10.1002/047084289X.rd114.pub2
7. ^ Thiele, J.; Günther, F. (1906). "Ueber Abkömmlinge des Dicyanhydrochinons". Justus Liebig'due south Annalen der Chemie. 349 (one): 45–66. doi:x.1002/jlac.19063490103.
8. ^ Walker, D.; Waugh, T. D. (1965). "2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Training". The Journal of Organic Chemical science. 30 (9): 3240. doi:ten.1021/jo01020a529.
9. ^ Rathore, Rajendra; Kochi, Jay K. (2000), "Donor/acceptor organizations and the electron-transfer image for organic reactivity", Advances in Physical Organic Chemical science, Elsevier, pp. 193–318, doi:ten.1016/s0065-3160(00)35014-vi, ISBN9780120335350
10. ^ Brown, Westward.; Turner, A. B. (1971). "Application of High-potential Quinones. vii. Synthesis of Steroidal Phenanthrenes by Double Methyl Migration". Journal of the Chemical Guild C: Organic. 1971: 2566–2572. doi:10.1039/J39710002566. PMID 5167256.
11. ^ Zhang, Y.; Li, C. J. (2006). "DDQ-Mediated Directly Cross-Dehydrogenative-Coupling (CDC) between Benzyl Ethers and Unproblematic Ketones". Journal of the American Chemical Society. 128 (thirteen): 4242–4243. doi:x.1021/ja060050p. PMID 16568995.

External links [edit]

• "Like Neurons in the Brain": A Molecular Figurer that Evolves

fenstermolet1994.blogspot.com

Source: https://en.wikipedia.org/wiki/2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

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