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84-58-2

Basic Information
CAS No.: 84-58-2
Name: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Article Data: 36
Molecular Structure:
Molecular Structure of 84-58-2 (2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)
Formula: C8Cl2N2O2
Molecular Weight: 227.006
Synonyms: DDQ (oxidizing agent);2,3-Dicyano-5,6-dichlorobenzoquinone;5,6-Dicyano-2,3-dichloro-p-benzoquinone;4,5-Dichloro-3,6-dioxo-1, 4-cyclohexadiene-1,2-dicarbonitrile;1,4-Cyclohexadiene-1,2-dicarbonitrile,4,5- dichloro-3,6-dioxo-;2,3-Dichloro-5,6-dicyano-p-quinone;5,6-Dichloro-2,3-dicyano-p-benzoquinone;Dichlorodicyano-p-benzoquinone;1,2-Dichloro-4,5-dicyanobenzoquinone;Dichlorodicyanoquinone;4-benzoquinone;1,2-Dicarbonitrile-4,5-dichloro-3,6-dioxo-1,4-cyclohexadiene;
EINECS: 201-542-2
Density: 1.7 g/cm3
Melting Point: 210-215 °C (dec.)(lit.)
Boiling Point: 301.8 °C at 760 mmHg
Flash Point: 136.3 °C
Solubility: reacts with water
Appearance: yellow to orange powder
Hazard Symbols: ToxicT
Risk Codes: 25-29-41-37/38-20/21-23/24/25
Safety: 22-24/25-37-45-36/37-26-36/37/39
Transport Information: UN 3439 6.1/PG 3
PSA: 81.72000
LogP: 1.17116
Synthetic route

C10H10N4O2

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
Stage #1: C10H10N4O2 With sodium chloride at 38℃; for 2h;
Stage #2: With ethyl 3-chloropropanoate; tetracarbonyl nickel at 45℃; for 3h; Temperature;
96%
4640-41-9

2,3-dichloro-5,6-dicyanohydroquinone

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
With nitric acid
6476-44-4

pyrene - 2,3-dichloro-5,6-dicyano-p-benzoquinone complex

A

129-00-0

pyrene

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In chloroform at 31℃; Equilibrium constant; Thermodynamic data; other temperatures, ΔH;
35079-56-2, 31366-25-3

[2,2']Bi[[1,3]dithiolylidene]

84-58-2

2,3-dichloro-5,6-dicyano-1,4-benzoquinone anion radical

A

31366-25-3

tetrathiafulvalene

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant;
99447-83-3

C14H13NO*C8Cl2N2O2

A

62500-20-3

(Z)-N-(3-methylbenzylidene)-1-phenylmethanamine oxide

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 25℃; Equilibrium constant;
99447-84-4

C14H13NO*C8Cl2N2O2

A

19865-55-5

N-(4-methylbenzylidene)aniline oxide

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 25℃; Equilibrium constant;

trans-stilbene - 2,3-dichloro-5,6-dicyano-p-benzoquinone complex

A

103-30-0

(E)-1,2-diphenyl-ethene

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In chloroform at 31℃; Equilibrium constant; Thermodynamic data; other temperatures, ΔH;

fluorene - 2,3-dichloro-5,6-dicyano-p-benzoquinone complex

A

86-73-7

9H-fluorene

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In chloroform at 31℃; Equilibrium constant; Thermodynamic data; other temperatures, ΔH;

2-bromofluorene - 2,3-dichloro-5,6-dicyano-p-benzoquinone complex

A

1133-80-8

2-bromo-9H-fluorene

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In chloroform at 31℃; Equilibrium constant; Thermodynamic data; other temperatures, ΔH;

C13H10ClNO*C8Cl2N2O2

A

35427-95-3, 141356-94-7

N-(2-chlorobenzylidene)aniline N-oxide

B

84-58-2

2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions
ConditionsYield
In dichloromethane at 25℃; Equilibrium constant;
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Standards and Recommendations

Purity ≥98.0% (GC)
Loss on drying  <0.5 % (80°C)
Ash<0.1 %

Specification

 1.Introduction of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

The 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone,with its CAS NO.84-58-2,is a kind of yellow to orange crystals. It is soluble in benzene, acetic acid, slightly soluble in chloroform and dichloromethane. It has synonyms of DDQ (oxidizing agent);2,3-Dicyano-5,6-dichlorobenzoquinone;5,6-Dicyano-2,3-dichloro-p-benzoquinone;4,5-Dichloro-3,6-dioxo-1, 4-cyclohexadiene-1,2-dicarbonitrile and 1,4-Cyclohexadiene-1,2-dicarbonitrile,4,5- dichloro-3,6-dioxo-. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone should be stored in shady and cool warehouse and mainly used in synthesis of steroidal compounds oxidant, for the use of family planning and chlormadinone acetate, three ene norgestrel production.

2.Properties of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

(1) Density: 1.7 g/cm3  (2) Melting Point: 210-215 °C (dec.)(lit.) (3) Boiling Point: 301.8 °C at 760 mmHg
(4) Index of Refraction: 1.601  (5) Molar Refractivity: 45.73 cm3  (6) Molar Volume: 133.4 cm3
(7) Surface Tension: 71.4 dyne/cm (8) Enthalpy of Vaporization: 54.2 kJ/mol (9) Vapour Pressure: 0.00103 mmHg at 25 °C
(10) Storage Temp.: 0-6 °C  (11)Water Solubility: reacts (12) Sensitive: moisture sensitive

(13) XLogP3-AA: 1.6  (14) H-Bond Acceptor: 4  (15) Exact Mass: 225.933683  (16) MonoIsotopic Mass: 225.933683
(17) Topological Polar Surface Area: 81.7  (18) Heavy Atom Count: 14
 

3.Structure descriptors of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

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

4.Safety data of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Hazard Codes: ToxicT
Risk Statements: 25-29-41-37/38-20/21-23/24/25
R25 :Toxic if swallowed.
R29:Contact with water liberates toxic gas.
R41:Risk of serious damage to the eyes.
R37/38:Irritating to respiratory system and skin.
R20/21:Harmful by inhalation and in contact with skin.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-24/25-37-45-36/37-26-36/37/39
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S37:Wear suitable gloves.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 3439 6.1/PG 3
WGK Germany: 3
RTECS: GU4825000
F: 21
HazardClass: 6.1
PackingGroup: II
HS Code: 29269095


5.Toxity data of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 31mg/kg (31mg/kg)   Chemotherapy Vol. 16, Pg. 371, 1971.
 
mouse LD50 intravenous 13mg/kg (13mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07894,