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84-58-2 molecular structure
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4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile

ChemBase ID: 77210
Molecular Formular: C8Cl2N2O2
Molecular Mass: 227.0038
Monoisotopic Mass: 225.93368261
SMILES and InChIs

SMILES:
ClC1=C(C(=O)C(=C(C1=O)C#N)C#N)Cl
Canonical SMILES:
N#CC1=C(C#N)C(=O)C(=C(C1=O)Cl)Cl
InChI:
InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13
InChIKey:
HZNVUJQVZSTENZ-UHFFFAOYSA-N

Cite this record

CBID:77210 http://www.chembase.cn/molecule-77210.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
IUPAC Traditional name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
Synonyms
* 2,3-Dichloro-5,6-dicyano-p-benzoquinone* 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile* Dichlorodicyanobenzoquinone
2,3-DICHLORO-5,6-DICYANOQUINONE
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
1,2-Dichloro-4,5-dicyano-3,6-dioxocyclohexa-1,4-diene
4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
2,3-Dichloro-5,6-dicyanobenzoquinone
1,2-Dichloro-4,5-dicyano-p-benzoquinone
2,3-Chloro-5,6-dicyanoquinone
2,3-Dichloro-5,6-dicyano-p-quinone
Dichlorodicyano-p-benzoquinone
Dicyanodichloroquinone
NSC 401087
2,3-Dichloro-5,6-dicyano-p-benzoquinone
DDQ
2,3-Dichloro-5,6-dicyano-p-benzoquinone
4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile
2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
4,5-二氯-3,6-二氧-1,4-环己二烯-1,2-二甲腈
2,3-二氯-5,6-二氰基对苯醌
2,3-二氯-5,6-二氰基苯醌
CAS Number
84-58-2
EC Number
201-542-2
MDL Number
MFCD00001593
Beilstein Number
747939
Merck Index
143063
PubChem SID
24893996
24861867
162042083
PubChem CID
6775
Chemspider ID
6517
Wikipedia Title
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.4257357  LogD (pH = 7.4) 1.4257357 
Log P 1.4257357  Molar Refractivity 50.7186 cm3
Polarizability 18.073162 Å3 Polar Surface Area 81.72 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Benzene expand Show data source
Ethyl Acetate expand Show data source
reacts in water expand Show data source
Apperance
Yellow Solid expand Show data source
yellow to orange powder expand Show data source
Melting Point
210-215 °C (dec.) expand Show data source
210-215 °C (dec.)(lit.) expand Show data source
210-215°C expand Show data source
214-218°C expand Show data source
219-221°C expand Show data source
Boiling Point
301.8°C @ 760mmHg expand Show data source
Flash Point
136.3°C expand Show data source
Density
1.7g/cm3 expand Show data source
Storage Condition
0°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
Moisture Sensitive expand Show data source
Toxic/Moisture Sensitive/Store under Argon expand Show data source
RTECS
GU4825000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
Irritant Irritant (Xi) expand Show data source
UN Number
3439 expand Show data source
UN3439 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
II expand Show data source
Risk Statements
25-29 expand Show data source
R:36/37/38 expand Show data source
R25 R29 expand Show data source
Safety Statements
22-24/25-37-45 expand Show data source
7/8-20-36-45 expand Show data source
S:20-25-26-37/39 expand Show data source
S22 S24/25 S37 S45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P264-P270-P301+P310-P321-P405-P501A expand Show data source
P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 3439 6.1/PG 3 expand Show data source
Supplemental Hazard Statements
Contact with water liberates toxic gas. expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥95.0% (RT) expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Download expand Show data source
Empirical Formula (Hill Notation)
C8Cl2N2O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 05209966 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02150864 external link
Orange-yellow crystals.
Dehydrogenation reagent. Also used as a spray reagent for carbazoles.
Sigma Aldrich - D60400 external link
Application
Used with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.1
Versatile deprotection reagent for a variety of compounds, such as thioacetals, acetals, and ketals. Useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.
Packaging
5, 10, 100 g in glass bottle
Sigma Aldrich - 35680 external link
Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds1; Reagent for the mild cleavage of ether-type protecting groups2,3,4
Toronto Research Chemicals - D434110 external link
An oxidizing agent, especially in steroid synthesis.

REFERENCES

REFERENCES

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  • • Silyl and THP ethers are deprotected: J. Chem. Soc., Perkin 1, 2997 (1992); Synth. Commun., 25, 2373 (1995), respectively. Ethers of benzylic or allylic alcohols are oxidized to aldehydes, permitting the use of the methoxymethyl group as a masked aldehyde: Can. J. Chem., 67, 699 (1989). For cleavage of thioacetals to carbonyl groups, see: J. Org. Chem., 58, 7576 (1993); Chem. Lett., 965 (1994).
  • • Widely used dehydrogenation reagent, e.g. in aromatization reactions; review: Chem. Rev., 67, 153 (1967); 78, 317 (1978). For an example, see: Org. Synth. Coll., 6, 731 (1988). Dehydrogenation of chromanones to chromones and flavanones to flavones: Synthesis, 310 (1983); spirocyclohexenones to the corresponding cross-conjugated dienones: Org. Synth. Coll., 7, 473 (1990).
  • • Catalyzes formation of THP ethers from alcohols: Bull. Chem. Soc. Jpn., 65, 304 (1992), the isopropylidenation of carbohydrates with 2,2-Dimethoxypropane, A13810: Acta Chem. Scand., 47, 843 (1993); and C-N bond formation e.g. imines from arylamines and aldehydes (see also 1,2-Dianilinoethane, B23098), and, with 1 mole of DDQ, benzimidazole formation: Tetrahedron, 51, 5813 (1995):
  • • For a brief feature on uses of the reagent in synthesis, see: Synlett, 196 (2006).
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PATENTS

PATENTS

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INTERNET

INTERNET

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