CAS No.4640-41-9,dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile Suppliers

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dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile

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Synthetic route

: 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

: 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%

: 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

: 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

: 91266-61-4
1-cyclopropyl-1-methyldibenzospiro<2.4>heptane

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

A: 4425-82-5
9-methylene-fluorene

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

C: 112145-98-9
7-(o,o'-biphenylene)-3,4-dichloro-1,6-dicyano-9-cyclopropylbicyclo<4.4.0>deca-3,8-diene-2,4-dione

Conditions

Conditions	Yield
In benzene Ambient temperature;	A 19% B 93% C 56%

...Expand

: ((1R,2S)-1-Methoxy-2-pentyl-cyclopropoxy)-trimethyl-silane

A: 7367-81-9
methyl (E)-oct-2-enoate

B: 35234-16-3
(E)-methyl oct-3-enoate

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

D: 69668-85-5
methyl (Z)-oct-3-enoate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 60℃; for 20h; Yields of byproduct given;	A 76% B n/a C 86% D n/a
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 60℃; for 20h; Yield given;	A 76% B n/a C 86% D n/a

...Expand

: 5273-86-9
C12H16O3

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

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

B: 106128-88-5
2,4,5-trimethoxy cinnamaldehyde

Conditions

Conditions	Yield
With acetic acid In 1,4-dioxane for 0.5h; Sonication;	A n/a B 85%

...Expand

: 142763-11-9
(S)-4-(3,4-dimethoxybenzyl)oxazolidin-2-one

: 64-18-6
formic acid

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

A: (R)-4-(3,4-dimethoxybenzoyl)oxazolidin-2-one

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

Conditions

Conditions	Yield
In water at 60℃; for 3h;	A 84% B n/a

...Expand

: (Z)-1-Methoxy-1-(trimethylsiloxy)-2-ethyl-2-phenylcyclopropane

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

B: 84009-51-8
(Z)-Methyl 3-phenyl-2-pentenoate

C: 84009-51-8
methyl (E)-3-phenyl-2-pentenoate

D: Methyl 3-phenyl-3-pentenoate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 6h; Heating; Yield given. Yields of byproduct given;	A 82% B n/a C n/a D 48%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 6h; Heating; Yield given;	A 82% B n/a C n/a D 48%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 6h; Heating; Yields of byproduct given;	A 82% B 48% C n/a D n/a

...Expand

: (Z)-1-Methoxy-1-(trimethylsiloxy)-2-isopropyl-2-phenylcyclopropane

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

B: 79238-26-9
methyl 4-methyl-3-phenyl-3-penten-1-oate

C: (Z)-Methyl 3-phenyl-4-methyl-2-pentenoate

D: (E)-Methyl 3-phenyl-4-methyl-2-pentenoate

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 15h; Heating;	A 77% B 14% C n/a D n/a
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 15h; Heating; Yield given;	A 77% B 14% C n/a D n/a
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 15h; Heating; Yield given. Yields of byproduct given;	A 77% B 14% C n/a D n/a

...Expand

: ((1R,2R)-1-Methoxy-2-phenyl-cyclopropoxy)-trimethyl-silane

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

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

B: 103-26-4
Methyl cinnamate

Conditions

Conditions	Yield
In tetrahydrofuran for 0.2h; Product distribution; Mechanism; Heating; reactions of derivatives with DDQ and chloranil under var. conditions;	A 65% B 74%

...Expand

: 37568-24-4
1,1-dicyclopropyl-dibenzospiro<2.4>heptane

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

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

B: 121125-21-1
1,4-bis<<4-cyclopropyl-5-(9-fluorenylidene)pent-3-enyl>oxy>-2,3-dichloro-5,6-dicyanobenzene

Conditions

Conditions	Yield
In benzene for 15h;	A 65% B 24%

...Expand

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

: 2071-20-7
bis-diphenylphosphinomethane

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

B: 1445314-69-1
3-[bis(diphenylphosphoryl)methyl]-4,5-dichloro-3-hydroxy-6-oxocyclohexa-1,4-diene-1,2-dicarbonitrile

C: 2071-21-8
bis(diphenylphosphoryl)methane

Conditions

Conditions	Yield
In tetrahydrofuran for 20h; Reflux;	A 5% B 65% C 15%

...Expand

: 1,1-Dimethoxy-2-methyl-2-phenylcyclopropane

A: 3461-38-9
3-methylenebenzenepropanoic acid methyl ester

B: 3461-50-5
methyl trans-3-methylcinnamate

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

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran Heating;	A 14% B 53% C 63%

...Expand

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

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

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

B: 5-chloro-6-hydroxy-4-oxo-1,4-dihydrobenzo[4,5]furo[2,3-d]pyrimidine-7,8-dicarbonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 48h;	A n/a B 63%

...Expand

: (Z)-1-Methoxy-1-(trimethylsiloxy)-2-methyl-2-phenylcyclopropane

A: 3461-38-9
3-methylenebenzenepropanoic acid methyl ester

B: 3461-50-5
methyl trans-3-methylcinnamate

C: 3461-50-5, 5440-87-9, 26423-89-2
methyl (Z)-3-phenyl-but-2-enoate

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

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 2h; Heating; Yields of byproduct given;	A 41% B n/a C n/a D 56%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 2h; Heating; Yield given;	A 41% B n/a C n/a D 56%

...Expand

: 107-21-1
ethylene glycol

: 124312-35-2
3',4'-dichloro-1',6'-dicyanospironorcarene>-2',5'-dione

A: 165-37-7
spiro<1,3-dioxolane-2,9'-fluorene>

B: 486-25-9
9-fluorenone

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

Conditions

Conditions	Yield
In acetonitrile for 4h; Ambient temperature;	A 56% B 26% C n/a

...Expand

: 124312-35-2
3',4'-dichloro-1',6'-dicyanospironorcarene>-2',5'-dione

: 504-63-2
trimethyleneglycol

A: 165-37-7
spiro<1,3-dioxolane-2,9'-fluorene>

B: 486-25-9
9-fluorenone

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

Conditions

Conditions	Yield
In acetonitrile Ambient temperature;	A 51% B 37% C n/a

...Expand

: 124312-35-2
3',4'-dichloro-1',6'-dicyanospironorcarene>-2',5'-dione

: 504-63-2
trimethyleneglycol

A: 486-25-9
9-fluorenone

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

C: spiro<1,3-dioxane-2,9'-fluorene>

Conditions

Conditions	Yield
In acetonitrile Ambient temperature;	A 37% B n/a C 51%

...Expand

: 4214-38-4, 22880-58-6
(diphenylmethylene)triphenylphosphorane

: 141-52-6
sodium ethanolate

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

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

B: 5,6-Dichloro-4,7-diethoxy-2,2-diphenyl-indan-1,3-diylidenediamine

Conditions

Conditions	Yield
In ethanol for 24h;	A 18% B 48%

...Expand

: 123439-12-3
4-amino[2.2]paracyclophane

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

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

B: 2-cyano-3-(4-<2.2>paracyclophanyl)amino-5,6-dichloro-1,4-benzoquinone

Conditions

Conditions	Yield
In ethyl acetate for 72h; Ambient temperature;	A n/a B 47%

...Expand

: 5351-58-6
benzaldehyde thiocarbohydrazone

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

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

B: N-[1,5,2,3]Oxathiadiazol-(4E)-ylidene-N'-[1-phenyl-meth-(Z)-ylidene]-hydrazine

C: 6,7-Dichloro-5-hydroxy-3-{[1-phenyl-meth-(Z)-ylidene]-hydrazono}-3H-indazole-4-carbonitrile

Conditions

Conditions	Yield
In ethyl acetate for 72h; Ambient temperature;	A 39% B 27% C 47%

...Expand

: 7484-46-0
S-methyl benzenylmethylene hydrazine dithiocarboxylate

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

A: 1925-71-9
2-methylmercapto-5-phenyl-1,3,4-thiadiazole

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

C: dimethyl N,N'-diphenylethanebis(thiohydrazonate)

Conditions

Conditions	Yield
In benzene for 48h; Mechanism; Ambient temperature; further azomethine educts; further dicyanoquinone reagents;	A 33% B n/a C 41%

...Expand

: 67-56-1
methanol

: 22293-10-3
(1-diazoethyl)benzene

A: 4316-35-2
acetophenone dimethyl acetal

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

Conditions

Conditions	Yield
In benzene at 25℃; for 1h;	A 36% B n/a

...Expand

: 24978-42-5, 24764-91-8
1,4-bis(4'-methoxyphenyl)-1,4-diazabuta-1,3-diene

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

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

B: 4,5-Dichloro-6-hydroxy-1-(4-methoxy-phenyl)-3-(4-methoxy-phenylamino)-1H-indole-7-carbonitrile

Conditions

Conditions	Yield
In ethyl acetate for 48h; Ambient temperature; Yields of byproduct given;	A n/a B 34%

...Expand

: 24764-92-9
1,4-bis(p-tolyl)-1,4-diaza-1,3-butadiene

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

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

B: 2-chloro-5,6-dicyano-3-p-toluidino-p-benzoquinone

C: 4,5-Dichloro-6-hydroxy-1-p-tolyl-3-p-tolylamino-1H-indole-7-carbonitrile

Conditions

Conditions	Yield
In ethyl acetate for 48h; Ambient temperature; Yield given;	A n/a B n/a C 32%
In ethyl acetate for 48h; Ambient temperature; Yields of byproduct given;	A n/a B n/a C 32%
In ethyl acetate for 48h; Product distribution; Mechanism; Ambient temperature;

...Expand

: 30834-76-5
glyoxal-bis(4-dimethylaminophenylimine)

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

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

B: 4-Chloro-5-(4-dimethylamino-phenylamino)-3,6-dioxo-cyclohexa-1,4-diene-1,2-dicarbonitrile

C: 4,5-Dichloro-1-(4-dimethylamino-phenyl)-3-(4-dimethylamino-phenylamino)-6-hydroxy-1H-indole-7-carbonitrile

Conditions

Conditions	Yield
In ethyl acetate for 48h; Ambient temperature; Yield given;	A n/a B n/a C 30%
In ethyl acetate for 48h; Ambient temperature; Yields of byproduct given;	A n/a B n/a C 30%

...Expand

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

: 121-45-9
phosphorous acid trimethyl ester

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

B: Phosphoric acid 2,3-dichloro-5,6-dicyano-4-hydroxy-phenyl ester dimethyl ester

C: Phosphoric acid 2,3-dichloro-5,6-dicyano-4-methoxy-phenyl ester dimethyl ester

Conditions

Conditions	Yield
In dichloromethane at -10 - 20℃;	A n/a B 20% C 18%

...Expand

: 67-56-1
methanol

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

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

B: 2,3-dichloro-5-cyano-6-methoxy-p-benzoquinone

Conditions

Conditions	Yield
for 48h; Ambient temperature;	A 20% B 14%

...Expand

: C34H28Fe2N2

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

: C34H28Fe2N2*2C8H2Cl2N2O2

Conditions

Conditions	Yield
In chloroform stirred, room temperature, 14 h; filtrn., washed (chloroform), elem. anal.;	89.7%

: C32H32Fe2N2

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

: C32H32Fe2N2*2C8H2Cl2N2O2

Conditions

Conditions	Yield
In chloroform stirred, room temperature, 14 h; filtrn., washed (chloroform), elem. anal.;	86.9%

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

: 92827-67-3
C20H20S4

: C20H19S4(1+)*ClO4(1-)

Conditions

Conditions	Yield
With perchloric acid at 50℃;	81%

: 112-30-1
1-Decanol

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

: 4,5-dichloro-3,6-didecyloxyphthalonitrile

Conditions

Conditions	Yield
Stage #1: 1-Decanol; 2,3-dichloro-5,6-dicyanohydroquinone With triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; for 20.5h; Mitsunobu Displacement; Inert atmosphere;	77.1%

: 15893-42-2
3-(4-methoxyphenyl)propionyl chloride

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

: 142834-89-7
3-(4-Methoxy-phenyl)-propionic acid 2,3-dichloro-5,6-dicyano-4-[3-(4-methoxy-phenyl)-propionyloxy]-phenyl ester

Conditions

Conditions	Yield
	76%

: C29H26Fe2N2O

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

: C29H26Fe2N2O*2C8H2Cl2N2O2

Conditions

Conditions	Yield
In chloroform stirred, room temperature, 14 h; filtrn., washed (chloroform), elem. anal.;	71.4%

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

: 102-92-1
Cinnamoyl chloride

: 142834-88-6
(E)-3-Phenyl-acrylic acid 2,3-dichloro-5,6-dicyano-4-[(E)-(3-phenyl-acryloyl)oxy]-phenyl ester

Conditions

Conditions	Yield
	70%

: 186581-53-3, 908094-01-9
diazomethane

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

: 4640-42-0
2,3-dicyano-5,6-dichloro-1,4-dimethoxybenzene

Conditions

Conditions	Yield
In diethyl ether at 0℃; for 0.75h;	67%

: 109-65-9
1-bromo-butane

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

: 116453-92-0
3,6-dibutoxy-4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 3h;	60%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 70 - 80℃; for 3h;	52%

: 628-17-1
amyl iodide

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

: 119429-67-3
4,5-dichloro-3,6-dipentyloxyphthalonitrile

Conditions

Conditions	Yield
	58%

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

: 75-03-6
ethyl iodide

: 111482-59-8
4,5-Dichloro-3,6-diethoxy-phthalonitrile

Conditions

Conditions	Yield
In diethyl ether for 60h;	55%

: 542-69-8
1-iodo-butane

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

: 116453-92-0
3,6-dibutoxy-4,5-dichlorophthalonitrile

Conditions

Conditions	Yield
In diethyl ether for 56h;	52%
With potassium hydroxide; tetrabutylammomium bromide at 100℃; for 18h;

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