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

Name
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
EINECS 201-542-2
CAS No. 84-58-2
Article Data36
CAS DataBase
Density 1.7 g/cm³
Solubility reacts with water
Melting Point 210-215 °C (dec.)(lit.)
Formula C₈Cl₂N₂O₂
Boiling Point 301.8 °C at 760 mmHg
Molecular Weight 227.006
Flash Point 136.3 °C
Transport Information UN 3439 6.1/PG 3
Appearance yellow to orange powder
Safety 22-24/25-37-45-36/37-26-36/37/39
Risk Codes 25-29-41-37/38-20/21-23/24/25
Molecular Structure
Hazard Symbols T
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;
PSA 81.72000
LogP 1.17116

Synthetic route

: C10H10N4O2

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In acetonitrile at 25℃; Equilibrium constant;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In dichloromethane at 25℃; Equilibrium constant;

: C13H10ClNO*C8Cl2N2O2

A: 32019-33-3
N-(3-chlorobenzylidene)aniline oxide

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 25℃; Equilibrium constant;

: C14H13NO2*C8Cl2N2O2

A: 99447-81-1
1-(3-methoxyphenyl)-N-phenylmethanimine oxide

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 25℃; Equilibrium constant;

: C14H13NO2*C8Cl2N2O2

A: 30924-55-1
1-(2-methoxyphenyl)-N-phenylmethanimine oxide

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 25℃; Equilibrium constant;

: N,N'-Bis-(4-methoxy-phenyl)-diazene N-oxide; compound with 4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 1562-94-3, 21650-70-4, 51437-65-1
4,4'-azoxy anisole

Conditions

Conditions	Yield
In dichloromethane at 25℃; Equilibrium constant;

: C30H26N2*C8Cl2N2O2

A: C30H26N2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C30H26N2*C8Cl2N2O2

A: 107348-22-1, 107538-42-1
N,N'-{[2.2]paracyclophane-4,13-diyldimethylylidene}dianiline

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C32H30N2*C8Cl2N2O2

A: 107348-32-3
C32H30N2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C32H30N2*C8Cl2N2O2

A: C32H30N2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C30H24Cl2N2*C8Cl2N2O2

A: 107348-28-7
C30H24Cl2N2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C30H24Cl2N2*C8Cl2N2O2

A: C30H24Cl2N2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C32H30N2O2*C8Cl2N2O2

A: C32H30N2O2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: C32H30N2O2*C8Cl2N2O2

A: 107348-26-5, 107538-46-5
C32H30N2O2

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane at 22℃; Equilibrium constant;

: 4,5-Dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with 2,2,6,6-tetramethyl-1-nitroso-piperidine

A: 6130-93-4
2,2,6,6-tetramethyl-1-nitrosopiperidine

B: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

Conditions

Conditions	Yield
In dichloromethane Equilibrium constant;

: 1,1,3,3-Tetramethyl-2-nitroso-2,3-dihydro-1H-isoindole; compound with 4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 1,1,3,3-Tetramethyl-2-nitroso-2,3-dihydro-1H-isoindole

Conditions

Conditions	Yield
In dichloromethane Equilibrium constant; Thermodynamic data; ΔH0, ΔS0;

: C14H22N2O*C8Cl2N2O2

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 176437-17-5
di-1-norbornylnitrosamine

Conditions

Conditions	Yield
In dichloromethane Equilibrium constant;

: C20H30N2O*C8Cl2N2O2

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 176437-16-4
di-1-adamantylnitrosamine

Conditions

Conditions	Yield
In dichloromethane Equilibrium constant;

: 4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with benzo[b]thiophene

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 95-15-8
Benzo[b]thiophene

Conditions

Conditions	Yield
In dichloromethane at 24℃; Equilibrium constant; decomplexation;

: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

: 7697-37-2
nitric acid

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile; compound with acenaphthylene

A: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

B: 208-96-8
acenaphthylene

Conditions

Conditions	Yield
In 1,2-dichloro-ethane Equilibrium constant;

: 603-76-9
1-methylindole

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 61995-39-9
4,5-Dichloro-3-hydroxy-1-(1-methyl-1H-indol-3-yl)-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In 1,4-dioxane for 24h; Ambient temperature;	100%

: 10075-50-0
5-bromo-1H-indole

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1-(5-Bromo-1H-indol-3-yl)-4,5-dichloro-3-hydroxy-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In 1,4-dioxane for 120h; Ambient temperature;	100%
In 1,4-dioxane at 20℃; for 0.5h;

: 1006-94-6
5-methoxylindole

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4,5-Dichloro-3-hydroxy-1-(5-methoxy-1H-indol-3-yl)-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In 1,4-dioxane for 2h; Ambient temperature;	100%
In 1,4-dioxane at 20℃; for 0.5h;

: 115843-45-3
1-<(4,5-dimethyl-2-phenyl-1,4-cyclohexadien-1-yl)sulphonyl>-4-methylbenzene

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 115843-46-4
4,5-dimethyl-2-<(4-methylphenyl)sulphonyl>-1,1'-biphenyl

Conditions

Conditions	Yield
In chloroform for 12h; Ambient temperature;	100%

: 67-56-1
methanol

: 29040-52-6
6-methoxy-3-methylbenzofuran

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4,5-Dichloro-3-(3,6-dimethoxy-3-methyl-2,3-dihydro-benzofuran-2-yloxy)-6-hydroxy-phthalonitrile

Conditions

Conditions	Yield
for 0.25h; Ambient temperature;	99%

...Expand

aqueous potassium carbonate: aqueous potassium carbonate

: 208510-90-1
7-methyl-6-nitroindoline

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 133053-70-0
7-methyl-6-nitroindole

Conditions

Conditions	Yield
In dichloromethane; benzene	99%

...Expand

: 120-72-9
indole

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 61995-38-8
4,5-Dichloro-3-hydroxy-1-(1H-indol-3-yl)-6-oxo-cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In 1,4-dioxane for 24h; Ambient temperature;	98%
In 1,4-dioxane at 20℃; for 0.5h;

: 58315-26-7
5,5'-Diphenyl-3,3'-bi(3H-1,2-dithiolyliden)

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 80695-50-7
(E)-5,5'-Diphenyl-[3,3']bi[[1,2]dithiolylidene]; compound with 4,5-dichloro-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
In carbon disulfide; benzene	98%

: 661-69-8
hexamethyldistannane

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 76279-10-2
C6Cl2(CN)2(OSn(CH3)3)2

Conditions

Conditions	Yield
In benzene keeping at room temp. (N2) for 20 h; various yields in various conditions; sepn., recrystn. from benzene; elem. anal.;	98%

: 166987-34-4
Pt((C2C5H4)Fe(C5H5))(P(C6H5)3)2(C6H4OCH3)

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: Pt((C2C5H4)Fe(C5H5))(P(C6H5)3)2(C6H4OCH3)(1+)*C6Cl2(CN)2O2(1-)=[Pt((C2C5H4)Fe(C5H5))(P(C6H5)3)2(C6H4OCH3)][C6Cl2(CN)2O2]

Conditions

Conditions	Yield
In dichloromethane; benzene N2-atmosphere; stirring (15 min); filtering; elem. anal.;	98%

: 1131759-20-0
C46H49N

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1131759-26-6
C92H96N2

Conditions

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In toluene at 25℃; for 0.166667h; Inert atmosphere;	98%

: 29040-52-6
6-methoxy-3-methylbenzofuran

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4,5-Dichloro-3-hydroxy-6-(6-methoxy-3-methyl-benzofuran-2-yloxy)-phthalonitrile

Conditions

Conditions	Yield
In benzene for 0.25h; Ambient temperature;	97%
In benzene for 0.25h; Mechanism; Ambient temperature; other solvents;

: 131323-89-2
1,1-di(thiophen-2-yl)ethan-1-ol

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

A: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

B: 132609-53-1
7,8-Dichloro-6,9-dioxo-4-thiophen-2-yl-6,9-dihydro-naphtho[2,1-b]thiophene-5a,9a-dicarbonitrile

Conditions

Conditions	Yield
In dichloromethane for 0.25h; Ambient temperature;	A n/a B 97%

...Expand

: methyl N-methyl-N-tosyl-L-tryptophanate

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: methyl (Z)-α-N-methyl-p-toluenesulfonamidoindole-3-acrylate

Conditions

Conditions	Yield
In tetrahydrofuran for 2h; Ambient temperature;	97%

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

Conditions

Conditions	Yield
With sodium disulfite	97%
With sodium hydrogencarbonate In water; toluene	97%
With 5,6-O-isopropylidene-L-ascorbic acid In 1,2-dimethoxyethane for 6h; UV-irradiation;	96%

: 102-54-5
ferrocene

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: [ferricinium][2,3-dichloro-5,6-dicyano-p-benzoquinone anion radical]

Conditions

Conditions	Yield
In benzene	97%
In benzene	97%
In not given

: 103816-91-7
dicarbonyl[1-4-η-5-(1,3-dihydroxy-2-propyl)cyclohepta-1,3-diene](triphenyl phosphite)iron

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 103816-96-2
Fe(CO)2(P(OC6H5)3)(C7H8(CH(CH2OH)CH2O))

Conditions

Conditions	Yield
In dichloromethane addn. of quinone to soln. of Fe-compd. (0°C), stirring (7.5 h); quenching with Et3N, poured into water, extn. (Et2O), drying (MgSO4), solvent removal, preparative TLC;	97%

: SNS[Al(OC(CF3)3)4]

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1008132-86-2
1SNS[Al(OC(CF3)3)4]

Conditions

Conditions	Yield
In liquid sulphur dioxide ligand (2.28 mmol) and Al compd. (2.10 mmol) stirred for 7 d; filtered, evapd. (vac.),;	97%

: (pS,S,P)-(C5H5)Fe(C5H3)(CH2CH2CCH)(CHCH2(C6H)(O)2CH3

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1318803-75-6, 1319747-23-3
(pS,M)-(C5H5)Fe(C5H3)CH2CH2(C4H2)(C6H)(O)2CH3

Conditions

Conditions	Yield
In dichloromethane treatment of Fe complex with C6Cl2O2(CN)2 in CH2Cl2 at room temp.;	97%

: 106266-06-2
Risperidone

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1425681-45-3
C23H27FN4O2*C8Cl2N2O2

Conditions

Conditions	Yield
In methanol at 20℃; for 0.75h; Equilibrium constant;	97%

: 13735-81-4
1-styrenyloxytrimethylsilane

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1449251-39-1
4,5-dichloro-3-hydroxy-6-oxo-1-(2-oxo-2-phenylethyl)cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 1-styrenyloxytrimethylsilane; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 0.0166667h; Stage #2: With silica gel In acetonitrile	97%

: 1833-53-0
2-(Trimethylsilyloxy)propene

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1449251-40-4
4,5-dichloro-3-hydroxy-6-oxo-1-(2-oxopropyl)cyclohexa-2,4-diene-1,2-dicarbonitrile

Conditions

Conditions	Yield
Stage #1: 2-(Trimethylsilyloxy)propene; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 0.0166667h; Stage #2: With silica gel In acetonitrile	97%

: 110-87-2
3,4-dihydro-2H-pyran

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

Conditions

Conditions	Yield
With oxygen; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 83℃; under 760.051 Torr; for 0.5h; Diels-Alder Cycloaddition; Reflux;	97%

: 67525-00-2
C17H16

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

A: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

B: 112145-99-0
7-(o,o'-biphenylene)-3,4-dichloro-1,6-dicyano-9-methylbicyclo<4.4.0>deca-3,8-diene-2,5-dione

Conditions

Conditions	Yield
In benzene for 12h; Heating;	A 96% B 78%

...Expand

: 67525-00-2
C17H16

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

A: 112145-99-0
7-(o,o'-biphenylene)-3,4-dichloro-1,6-dicyano-9-methylbicyclo<4.4.0>deca-3,8-diene-2,5-dione

B: 67902-00-5
2,3-dichloro-5,6-dicyano-p-hydroquinone

Conditions

Conditions	Yield
In benzene Heating;	A 78% B 96%

...Expand

: 132609-51-9
7-Thiophen-2-yl-3a,6-dihydro-benzo[b]thiophene-4,4,5,5-tetracarbonitrile

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

A: 4640-41-9
2,3-dichloro-5,6-dicyanohydroquinone

B: 132609-54-2
7-Thiophen-2-yl-benzo[b]thiophene-4,4,5,5-tetracarbonitrile

Conditions

Conditions	Yield
In dichloromethane for 0.0833333h;	A n/a B 96%

...Expand

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 2-iminobis(propenoic acid) dimethyl ester

: 5,6-dichloro-3,8-dicyano-7-hydroxy-4-oxo-11-azatricyclo[5.4.0.03,8]undeca-5,9-diene-1,10-dicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
In toluene for 2.5h; Cycloaddition; Heating;	96%

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 213971-37-0
3,4-dihydro-6,7-dimethoxy-3-methyl-5-n-propyl-1(2H)naphthalenone

A: 213971-21-2
6-Bromo-2,3-dimethoxy-1,7-dimethylnaphthalene

B: 213971-38-1
2,3-Dimethoxy-7-methyl-1-n-propylnaphthalene

Conditions

Conditions	Yield
With hydrogenchloride; sodium borohydrid In dichloromethane; isopropyl alcohol; benzene	A n/a B 96%

...Expand

: 1353640-13-7
6,13-dihydropentacene-2,3,9,10-tetracarboxylic acid tetrakis(3,5-bis(3,5-dimethoxy)benzyloxy)ester

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: C70H54Cl2N2O18

Conditions

Conditions	Yield
In toluene at 50℃; for 3h; Inert atmosphere; Darkness;	96%

: 1-(5-methylhex-4-enyloxy)-4-nitrobenzene

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: (+/-)-(4aRS,5RS,8aSR)-2,3-dichloro-7-methyl-5-(2-(4-nitrophenoxy)ethyl)-1,4-dioxo-1,4,4a,5,8,8a-hexahydronaphthalene-4a,8a-dicarbonitrile

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 60h; Diels-Alder Cycloaddition; diastereoselective reaction;	96%

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Standards and Recommendations

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

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone 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: Toxic T
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,

Product Name

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

Synthetic route

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Standards and Recommendations

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

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