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1448-87-9

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1448-87-9 Usage

Description

2-Chloroquinoxaline, also known as QCI, is a chemical compound with the molecular formula C8H5ClN2. It is a white to grey to purple or light brown powder, which is known for its various applications in different industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
2-Chloroquinoxaline is used as a reagent for the synthesis of various pharmaceutical compounds, such as chloroquinoxaline sulfamide. It plays a crucial role in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2-Chloroquinoxaline is utilized to study the effect of solvent on hydrolysis in aqueous-organic solvent mixtures, such as acetonitrile and dimethylesulphoxide. This helps researchers understand the behavior of the compound in different solvent environments and optimize reaction conditions for various chemical processes.
Used in Organic Synthesis:
2-Chloroquinoxaline is also used in the synthesis of complex organic molecules, such as 2-(3-butynyl-2-methyl-2-ol) quinoxaline. Its unique chemical structure allows it to be a valuable building block for the creation of novel compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 1448-87-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,4 and 8 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1448-87:
(6*1)+(5*4)+(4*4)+(3*8)+(2*8)+(1*7)=89
89 % 10 = 9
So 1448-87-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H5ClN2/c9-8-5-10-6-3-1-2-4-7(6)11-8/h1-5H

1448-87-9 Well-known Company Product Price

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  • Aldrich

  • (136301)  2-Chloroquinoxaline  98%

  • 1448-87-9

  • 136301-1G

  • 351.00CNY

  • Detail
  • Aldrich

  • (136301)  2-Chloroquinoxaline  98%

  • 1448-87-9

  • 136301-5G

  • 1,168.83CNY

  • Detail

1448-87-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloroquinoxaline

1.2 Other means of identification

Product number -
Other names 3-chloroquinoxaline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1448-87-9 SDS

1448-87-9Synthetic route

2-hydroxyquinoxaline
1196-57-2

2-hydroxyquinoxaline

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With pyridine; trichlorophosphate at 160℃; for 2h; Autoclave; neat (no solvent);94%
With dmap; thionyl chloride; bis(trichloromethyl) carbonate for 6.5h; Reflux; Green chemistry;94%
With P,P-dichlorophenylphosphine oxide at 110℃; for 12h; Inert atmosphere;81%
quinoxalin-2(1)-one
1196-57-2

quinoxalin-2(1)-one

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With trichlorophosphate In toluene for 1h; Reflux;93%
With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane for 4h; Heating;88%
With trichloroisocyanuric acid; triphenylphosphine In toluene for 4h; Heating;77%
benzoimidazole
51-17-2

benzoimidazole

chloroform
67-66-3

chloroform

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

phthalonitrile
91-15-6

phthalonitrile

Conditions
ConditionsYield
at 390 - 400℃;A 12%
B 88%
2,6-dichloroquinoxaline
18671-97-1

2,6-dichloroquinoxaline

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With 18-crown-6 ether; 4 A molecular sieve; cesium fluoride In tetrahydrofuran for 20h; Product distribution; Ambient temperature; other 6-substituted 2-chloroquinoxalines; var. temp., reaction time and stoichiometry of reagents;87%
3-chloroquinoxaline 1-oxide
5227-59-8

3-chloroquinoxaline 1-oxide

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With sodium dimethyl phosphonate In tetrahydrofuran at 20℃; for 4h;85%
C22H15N3O2
120569-15-5

C22H15N3O2

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

benzophenone
119-61-9

benzophenone

C

hexachloroethane
67-72-1

hexachloroethane

D

benzophenone azine
983-79-9

benzophenone azine

Conditions
ConditionsYield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;A 74%
B n/a
C n/a
D n/a
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With N,N-dimethyl-formamide; trichlorophosphate In dichloromethane at 0 - 25℃; Inert atmosphere; regioselective reaction;63%
With trichlorophosphate
diphenyl(quinoxalin-2-yl)(6-(trifluoromethyl)pyridin-3-yl)phosphonium trifluoromethanesulfonate

diphenyl(quinoxalin-2-yl)(6-(trifluoromethyl)pyridin-3-yl)phosphonium trifluoromethanesulfonate

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
With lithium chloride In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;60%
1-(2-Azido-phenyl)-4-chloro-1H-pyrazole

1-(2-Azido-phenyl)-4-chloro-1H-pyrazole

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

2-chloro-5H-benzo[d]pyrazolo[1,2-a][1,2,3]triazolylium betaine

2-chloro-5H-benzo[d]pyrazolo[1,2-a][1,2,3]triazolylium betaine

Conditions
ConditionsYield
at 450℃; under 0.01 Torr;A 54%
B n/a
at 450℃; under 0.01 Torr;A n/a
B 54%
quinoxalin-2(1)-one
1196-57-2

quinoxalin-2(1)-one

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

2-chloroquinoxaline-6-sulfonyl chloride
877078-00-7

2-chloroquinoxaline-6-sulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid; thionyl chloride at 110℃; for 11h;A 8.5 g
B 44%
6-chloro-1,2-dihydroquinoxalin-2-one
2427-71-6

6-chloro-1,2-dihydroquinoxalin-2-one

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

2,6-dichloroquinoxaline
18671-97-1

2,6-dichloroquinoxaline

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamideA n/a
B 41%
2-hydrazinoquinoxaline
61645-34-9

2-hydrazinoquinoxaline

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

2-hydroxyquinoxaline
1196-57-2

2-hydroxyquinoxaline

Conditions
ConditionsYield
With copper(I) chloride; hydrogenchloride; selenium(IV) oxide In water 1) 20 to 25 deg C 2) heating to boiling point;A 10%
B 13%
3-Chloroquinoxaline-2-carboxylic acid
20254-76-6

3-Chloroquinoxaline-2-carboxylic acid

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
at 160℃; under 1 Torr;
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

B

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

C

quinoxaline-6-carbonitrile
23088-24-6

quinoxaline-6-carbonitrile

D

quinoxaline-5-carbonitrile
77130-32-6

quinoxaline-5-carbonitrile

E

2-hydroxyquinoxaline
1196-57-2

2-hydroxyquinoxaline

F

quinoxaline-2-carbonitrile
7483-33-2

quinoxaline-2-carbonitrile

Conditions
ConditionsYield
With benzoyl chloride In dichloromethane for 3h; Product distribution; Ambient temperature; different cyanides, reagents, catalyst, solvents, reaction times and temperatures;
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

A

2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

B

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

C

6-chloroquinoxaline
5448-43-1

6-chloroquinoxaline

D

quinoxaline-2-carbonitrile
7483-33-2

quinoxaline-2-carbonitrile

Conditions
ConditionsYield
With potassium cyanide; benzoyl chloride In chloroform; water for 0.5h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

6-chloroquinoxaline
5448-43-1

6-chloroquinoxaline

Conditions
ConditionsYield
With trichlorophosphate for 0.166667h; Heating;A 90 % Chromat.
B 10 % Chromat.
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

A

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B

6-chloroquinoxaline
5448-43-1

6-chloroquinoxaline

C

5-chloro-quinoxaline
62163-09-1

5-chloro-quinoxaline

D

2-hydroxyquinoxaline
1196-57-2

2-hydroxyquinoxaline

Conditions
ConditionsYield
With potassium cyanide; water; benzoyl chloride In methanol for 2h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given;
quinoxaline-N-oxide
6935-29-1

quinoxaline-N-oxide

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: 30 percent alkaline hydrogen peroxide
3: phosphoryl chloride, phosphorus pentachloride / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: ethanol
2: POCl3
View Scheme
Multi-step reaction with 2 steps
1: H2O
2: POCl3; PCl5
View Scheme
3,4-dihydro-2-hydroxyquinoxaline
59564-59-9

3,4-dihydro-2-hydroxyquinoxaline

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 30 percent alkaline hydrogen peroxide
2: phosphoryl chloride, phosphorus pentachloride / 3 h / Heating
View Scheme
2,3-diethynylquinoxaline
91-19-0

2,3-diethynylquinoxaline

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: peroxyacetic acid; acetic acid
2: POCl3
View Scheme
ethyl 2-quinoxalinecarboxylate 4-oxide
23395-75-7

ethyl 2-quinoxalinecarboxylate 4-oxide

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3
2: aqueous methanol.NaCN
3: 160 °C / 1 Torr
View Scheme
ethyl 3-chloroquinoxaline-2-carboxylate
49679-45-0

ethyl 3-chloroquinoxaline-2-carboxylate

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous methanol.NaCN
2: 160 °C / 1 Torr
View Scheme
ethyl 3-oxo-4H-quinoxaline-2-carboxylate
36818-07-2

ethyl 3-oxo-4H-quinoxaline-2-carboxylate

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3
2: aqueous methanol.NaCN
3: 160 °C / 1 Torr
View Scheme
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

2-(trimethylsilylethynyl)quinoxaline
189629-50-3

2-(trimethylsilylethynyl)quinoxaline

Conditions
ConditionsYield
With triethylamine; triphenylphosphine; palladium diacetate; copper(l) iodide for 3.5h;100%
With triethylamine; triphenylphosphine; copper(l) iodide; palladium diacetate In acetonitrile Heating;54%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

N-tert-Butoxycarbonyl-1-amino-3-propyne
92136-39-5

N-tert-Butoxycarbonyl-1-amino-3-propyne

(3-quinoxalin-2-yl-prop-2-ynyl)-carbamic acid tert-butyl ester
892860-24-1

(3-quinoxalin-2-yl-prop-2-ynyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In acetonitrile at 20℃; for 2h;99%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

C31H24N4O2
1020725-59-0

C31H24N4O2

Conditions
ConditionsYield
Stage #1: BPA With potassium carbonate In sulfolane; toluene at 20℃; for 0.75h;
Stage #2: 2-chloroquinoxaline at 80℃; for 48h; Further stages.;
99%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

B-2-(E)-(4-phenyl-but-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

B-2-(E)-(4-phenyl-but-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-[(E)-4-phenylbut-1-enyl]quinoxaline
1252605-97-2

2-[(E)-4-phenylbut-1-enyl]quinoxaline

Conditions
ConditionsYield
With palladium diacetate; triphenylphosphine; cesium fluoride In water; acetonitrile for 4h; Reflux;99%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

(E)-3-(3-hydroxyphenyl)acrylic acid ethyl ester
96251-92-2

(E)-3-(3-hydroxyphenyl)acrylic acid ethyl ester

C19H16N2O3
1310877-61-2

C19H16N2O3

Conditions
ConditionsYield
With potassium carbonate In tetrachloromethane for 12h; Reflux; Inert atmosphere;99%
pyrrolidine
123-75-1

pyrrolidine

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(pyrrolidin-1-yl)quinoxaline
60814-24-6

2-(pyrrolidin-1-yl)quinoxaline

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; 4-phenyl-N-methylpyridinium iodide; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In dimethyl sulfoxide at 60℃; for 2h; Reagent/catalyst; Inert atmosphere;99%
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: pyrrolidine With triethylamine In N,N-dimethyl-formamide at 23℃; for 4h; Schlenk technique; Inert atmosphere;
92%
With potassium phosphate In water at 100℃; for 2h;89%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(4-methylpiperazin-1-yl)quinoxaline

2-(4-methylpiperazin-1-yl)quinoxaline

Conditions
ConditionsYield
at 160℃; for 0.0833333h; Microwave irradiation;98%
at 160℃; for 0.0833333h; microwave irradiation;94%
at 130℃; for 2h;80%
With indium(III) chloride In acetonitrile at 140℃; for 1h; Microwave irradiation; regioselective reaction;75%
In ethanol at 225℃; under 90009 Torr; for 0.266667h; Flow reactor;60%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

(2,4-dimethoxyphenyl)zinc chloride
109384-40-9

(2,4-dimethoxyphenyl)zinc chloride

2-(2,4-dimethoxyphenyl)quinoxaline
6592-18-3

2-(2,4-dimethoxyphenyl)quinoxaline

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 20℃; for 15h; Negishi coupling;98%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

tris(3-(diethoxymethyl)phenyl)bismuthine

tris(3-(diethoxymethyl)phenyl)bismuthine

2-(2-(diethoxymethyl))quinoxaline

2-(2-(diethoxymethyl))quinoxaline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere; Sealed tube;98%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-propylzinc bromide lithium chloride

2-propylzinc bromide lithium chloride

2-isopropylquinoxaline
80360-35-6

2-isopropylquinoxaline

Conditions
ConditionsYield
With C20H29N2P*BF4(1-)*H(1+); palladium diacetate In tetrahydrofuran; toluene at 0 - 20℃; for 2h; Negishi Coupling; Inert atmosphere;98%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

N-butylamine
109-73-9

N-butylamine

N-butylquinoxalin-2-amine
46416-44-8

N-butylquinoxalin-2-amine

Conditions
ConditionsYield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;98%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

1-bromo-2-naphthol
573-97-7

1-bromo-2-naphthol

2-(1-bromonaphthalen-2-yloxy)quinoxaline

2-(1-bromonaphthalen-2-yloxy)quinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: 1-bromo-2-naphthol With potassium phosphate In N,N-dimethyl-formamide at 60℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;
98%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

3,3,3-triethoxypropyne
42217-00-5

3,3,3-triethoxypropyne

2-(3,3,3-Triethoxypropyn-1-yl)quinoxaline
352197-16-1

2-(3,3,3-Triethoxypropyn-1-yl)quinoxaline

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate In acetonitrile at 70℃; for 3h;97%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-thiopheneboronic acid MIDA ester
1158984-92-9

2-thiopheneboronic acid MIDA ester

2-(thiophen-2-yl)quinoxaline
40353-41-1

2-(thiophen-2-yl)quinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline; 2-thiopheneboronic acid MIDA ester With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In 1,4-dioxane at 23℃; for 0.166667h; Inert atmosphere;
Stage #2: With potassium phosphate; water In 1,4-dioxane at 23 - 60℃; for 6.5h; Inert atmosphere;
97%
tris-(3-methoxy-phenyl)-bismuthane
95149-16-9

tris-(3-methoxy-phenyl)-bismuthane

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(3-methoxyphenyl)quinoxaline
71897-08-0

2-(3-methoxyphenyl)quinoxaline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere; Sealed tube;97%
pyrrole
109-97-7

pyrrole

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(1H-pyrrol-2-yl)quinoxalin-1-ium chloride

2-(1H-pyrrol-2-yl)quinoxalin-1-ium chloride

Conditions
ConditionsYield
With indium(III) chloride In dichloromethane at 120℃; for 1h; Microwave irradiation; regioselective reaction;97%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

(5-chlorothiophen-2-yl)boronic acid

(5-chlorothiophen-2-yl)boronic acid

2-(5-chloro-thiophen-2-yl)quinoxaline

2-(5-chloro-thiophen-2-yl)quinoxaline

Conditions
ConditionsYield
With potassium phosphate; 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl; tris(dibenzylideneacetone)dipalladium (0) In tert-Amyl alcohol at 100℃; for 4h; Suzuki-Miyaura reaction;96%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylquinoxaline
5021-43-2

2-phenylquinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline; phenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 25℃; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
96%
With C23H37Cl2N2PPd; sodium hydroxide In methanol; toluene at 80℃; for 24h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h;84%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h;84%
With potassium phosphate In water at 20℃; for 48h; Suzuki-Miyaura Coupling; Inert atmosphere; Irradiation;73%
piperazine
110-85-0

piperazine

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(1-piperazinyl)-quinoxaline
55686-91-4

2-(1-piperazinyl)-quinoxaline

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-dicyclohexylphosphino-2′,6′-di-i-propoxy-1,1′-biphenyl; sodium t-butanolate In 1,4-dioxane at 100℃; for 0.166667h;95%
In toluene for 24h; Reflux;40%
In iso-butanol for 16h; Heating;
microwave irradiation;
In butan-1-ol Reflux;
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

aniline
62-53-3

aniline

2-(phenylamino)quinoxalin-1-ium chloride

2-(phenylamino)quinoxalin-1-ium chloride

Conditions
ConditionsYield
With indium(III) chloride In acetonitrile at 120℃; for 1h; Microwave irradiation; regioselective reaction;95%
In methanol at 40℃; Rate constant; Thermodynamic data; Kinetics; further solvents and temperatures; ΔH(excit), ΔS(excit);
In methanol at 40℃;
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

meta-nitrophenol
554-84-7

meta-nitrophenol

2-(3-nitrophenoxy)quinoxaline

2-(3-nitrophenoxy)quinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: meta-nitrophenol With potassium phosphate In N,N-dimethyl-formamide at 60℃; for 2h; Schlenk technique; Inert atmosphere;
95%
With potassium hydroxide In N,N-dimethyl-formamide at 90℃; for 78h; Etherification;68%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

tetradecylmagnesium bromide
88303-25-7

tetradecylmagnesium bromide

2-tetradecyl-quinoxaline

2-tetradecyl-quinoxaline

Conditions
ConditionsYield
With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one95%
Stage #1: 2-chloroquinoxaline; tetradecylmagnesium bromide; iron-(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 0.0833333 - 0.166667h;
Stage #2: With water In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether Product distribution / selectivity;
95%
iron catalyst Product distribution / selectivity;95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

aniline
62-53-3

aniline

N-phenylquinoxalin-2-ylamine
15033-86-0

N-phenylquinoxalin-2-ylamine

Conditions
ConditionsYield
at 150℃; for 0.25h; Microwave irradiation; Neat (no solvent);95%
at 180℃;
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

N-3-(trifluoromethylphenyl)quinoxalin-2-ylamine
874765-16-9

N-3-(trifluoromethylphenyl)quinoxalin-2-ylamine

Conditions
ConditionsYield
at 150℃; for 0.25h; Microwave irradiation; Neat (no solvent);95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

4-acetylphenylboronic acid
149104-90-5

4-acetylphenylboronic acid

1-(4-(quinoxalin-2-yl)phenyl)ethanone
1346137-00-5

1-(4-(quinoxalin-2-yl)phenyl)ethanone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide; water at 100℃; for 4h; Suzuki-Miyaura coupling;95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2,4-difluorobromobenzene
348-57-2

2,4-difluorobromobenzene

2-(2,4-difluorophenyl)quinoxaline
930781-41-2

2-(2,4-difluorophenyl)quinoxaline

Conditions
ConditionsYield
Stage #1: 2,4-difluorobromobenzene With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
Stage #3: 2-chloroquinoxaline With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); XPhos In tetrahydrofuran at 20℃; for 12h; Negishi Coupling; Inert atmosphere;
95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

para-tert-butylphenol
98-54-4

para-tert-butylphenol

2-(4-tert-butylphenoxy)quinoxaline

2-(4-tert-butylphenoxy)quinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: para-tert-butylphenol With potassium phosphate In N,N-dimethyl-formamide at 60℃; for 2h; Schlenk technique; Inert atmosphere;
95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

1-methyl-1-propanethiol
513-53-1

1-methyl-1-propanethiol

2-(sec-butylthio)quinoxaline

2-(sec-butylthio)quinoxaline

Conditions
ConditionsYield
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: 1-methyl-1-propanethiol With potassium phosphate In N,N-dimethyl-formamide at 50℃; for 2h; Schlenk technique; Inert atmosphere;
95%
2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

decylthiol
143-10-2

decylthiol

2-(decylthio)quinoxaline

2-(decylthio)quinoxaline

Conditions
ConditionsYield
at 28℃; for 12h;95%
piperidine
110-89-4

piperidine

2-chloroquinoxaline
1448-87-9

2-chloroquinoxaline

2-(piperidin-1-yl)quinoxaline
34548-26-0

2-(piperidin-1-yl)quinoxaline

Conditions
ConditionsYield
In diethyl ether Ambient temperature;94%
With 1,3-bis-(diphenylphosphino)propane; potassium carbonate; cobalt(II) chloride In para-xylene at 135℃; for 3h; Inert atmosphere;91%
Stage #1: 2-chloroquinoxaline With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: piperidine With triethylamine In N,N-dimethyl-formamide at 23℃; for 4h; Schlenk technique; Inert atmosphere;
91%

1448-87-9Relevant articles and documents

-

Castle,R.N.,Onda,M.

, p. 954 - 956 (1961)

-

An improved method for chlorination of nitrogen-containing π-deficient heteroaromatics using triphenylphosphine and trichloroisocyanuric acid

Sugimoto, Osamu,Tanji, Ken-ichi

, p. 181 - 185 (2005)

Phosphorus compound prepared by reaction of triphenylphosphine with trichloroisocyanuric acid was found to be applied to chlorination of nitrogen-containing π-deficient heteroaromatics. As self-decomposition of the chlorinating reagent hardly proceeds, the reagent is more useful than phosphorus compound prepared by triphenylphosphine and N-chlorosuccinimide.

Novel gas-phase cyclisation reactions of 2-(1-pyrazolyl)phenylnitrenes

Clark, Bernard A. J.,McNab, Hamish,Sommerville, Craig C.

, p. 1211 - 1212 (1996)

Flash vacuum pyrolysis of the azide 3 gives a mixture of pyrazolobenzotriazole 2, quinoxaline 5 and pyrazolobenzimidazole 4 derived from the corresponding nitrene.

One-pot multicomponent synthesis of novel 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives, using a novel sulfamic acid functionalized Fe3O4 MNPs as highly effective nanocatalyst

Esam, Zohreh,Akhavan, Malihe,Bekhradnia, Ahmadreza

, (2020/10/27)

The immobilization of sulfonic acid on the surface of Fe3O4 magnetic nanoparticles (MNPs) as a novel acid nanocatalyst has been successfully reported. The morphological features, thermal stability, magnetic properties, and other physicochemical properties of the prepared superparamagnetic core–shell (Fe3O4@PFBA–Metformin@SO3H) were thoroughly characterized using Fourier transform infrared (FTIR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), thermogravimetric analysis–differential thermal analysis (TGA-DTA), atomic force microscopy (AFM), dynamic light scattering (DLS), Brunauer–Emmett–Teller (BET), and vibrating sample magnetometer (VSM) techniques. It was applied as an efficient and reusable catalyst for the synthesis of 2-(piperazin-1-yl) quinoxaline and benzimidazole derivatives via a one-pot multiple-component cascade reaction under green conditions. The results displayed the excellent catalytic activity of Fe3O4@PFBA–metformin@SO3H as an organic–inorganic hybrid nanocatalyst in condensation and multicomponent Mannich-type reactions. The easy separation, simple workup, excellent stability, and reusability of the nanocatalyst and quantitative yields of products and short reaction time are some outstanding advantages of this protocol.

Design and Synthesis of Some New N-Phenyl-[1,2,4]triazolo[4,3-a]quinoxaline-1-sulfonamide Derivatives and Their Anti-Cancer Activity

Badithapuram, Vinitha,Bandari, Srinivas,Dasari, Gouthami,Nukala, Satheesh Kumar,Pandiri, Madhuri

, p. 2280 - 2285 (2021/12/23)

Abstract: Synthesis of some new derivatives of N-phenyl-[1,2,4]triazolo [4,3-a]quinoxaline-1-sulfonamide and their in vitro anticancer activity on four human cancer lines like MCF-7 (human breast cancer cell line), HeLa (human cervical cancer cell line), A549 (human lung cancer cell line), and IMR32 (human neuroblastoma cell line) have been studied. Among the products, N-(3,5-dichloronitrophenyl)-[1,2,4] triazolo[4,3-a]quinoxaline-1-sulfonamide, is characterized by the activity higher than the standard Etoposide against the tested cancer cell lines.

Multifunctional quinoxaline-hydrazone derivatives with acetylcholinesterase and monoamine oxidases inhibitory activities as potential agents against Alzheimer’s disease

Ilgin, Sinem,Karaduman, Abdullah Burak,Levent, Serkan,Osmaniye, Derya,?avu?o?lu, Betül Kaya,?evik, Ulviye Acar,?zkay, Yusuf,Kaplancikli, Zafer As?m,Karaburun, Ahmet ?a?r?,Sa?lik, Begüm Nurpelin,Turan, Gülhan

, p. 1000 - 1011 (2020/04/29)

Multitarget molecules are considered as an effective way for the treatment of AD, instead of the classic one-drug-one-target strategy because of the multifactorial nature of AD. A variety of studies indicate that several enzymes inhibitors can be useful in the treatment of AD, including acetylcholinesterase (AchE), butyrylcholinesterase (BuChE) and monoamine oxidase (MAO). Various substituted quinoxaline-hydrazone derivatives were synthesized, and their activity in vitro were investigated, including AChE/BuChE inhibitory activity and MAOA/B inhibitory activity. Based on the experimental results, compound 5l exhibited good inhibitory potency on both AchE (IC50 = 0.028 ± 0.001 μM) and monoamine oxidase B (IC50 = 0.046 ± 0.002 μM). Molecular modeling studies showed that 5l could bind to the active site of AChE and MAO-B. Taken together, these results suggested that compound 5l might be a potential multifunctional agent for the treatment of AD.

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