Product Name

  • Name

    2-Chloropyrazine

  • EINECS 238-517-0
  • CAS No. 14508-49-7
  • Article Data25
  • CAS DataBase
  • Density 1.303 g/cm3
  • Solubility insoluble in water
  • Melting Point 153~154℃
  • Formula C4H3ClN2
  • Boiling Point 155.3 °C at 760 mmHg
  • Molecular Weight 114.534
  • Flash Point 57 °C
  • Transport Information UN 1993 3/PG 3
  • Appearance clear colorless to yellowish liquid
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 14508-49-7 (2-Chloropyrazine)
  • Hazard Symbols IrritantXi
  • Synonyms Pyrazine,chloro- (6CI,7CI,8CI,9CI);Pyrazine,2-chloro-;Chloropyrazine;Pyrazin-2-ylchloride;
  • PSA 25.78000
  • LogP 1.13000

Synthetic route

2-hydroxypyrazine sodium salt
24387-68-6

2-hydroxypyrazine sodium salt

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With thionyl chloride; N-ethyl-N,N-diisopropylamine In chloroform at 65℃; for 2h; Reagent/catalyst;95.4%
pyrazin-2-ol
6270-63-9

pyrazin-2-ol

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With dmap; thionyl chloride; bis(trichloromethyl) carbonate for 10.5h; Reflux; Green chemistry;89%
With trichlorophosphate for 0.666667h; Heating;84%
With trichlorophosphate
2-pyrazylcarboxylic acid
98-97-5

2-pyrazylcarboxylic acid

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With thionyl chloride In pyridine; para-tert-butylphenol; benzene75%
Pyrazin-N-Oxid(PyzNO)
2423-65-6

Pyrazin-N-Oxid(PyzNO)

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With trichlorophosphate at 70℃; for 2h;37%
With trichlorophosphate35%
Pyrazin-N-Oxid(PyzNO)
2423-65-6

Pyrazin-N-Oxid(PyzNO)

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

Pyrazine 1-oxide; hydrochloride

Pyrazine 1-oxide; hydrochloride

C

1-(2-pyrazinyl) pyrazinium salt

1-(2-pyrazinyl) pyrazinium salt

Conditions
ConditionsYield
With trichlorophosphate for 0.5h; Product distribution; Ambient temperature;A 13%
B 30%
C n/a
1,4-pyrazine
290-37-9

1,4-pyrazine

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With chlorine at 500℃;
With water; chlorine at 450℃;
pyrazin-2(1H)-one
6270-63-9

pyrazin-2(1H)-one

2-chloropyrazin
14508-49-7

2-chloropyrazin

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate
With trichlorophosphate
1H-imidazole
288-32-4

1H-imidazole

chloroform
67-66-3

chloroform

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

Conditions
ConditionsYield
at 550℃; Yield given. Yields of byproduct given;
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

chloroform
67-66-3

chloroform

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

1H-pyrrole-2-carbonitrile
4513-94-4

1H-pyrrole-2-carbonitrile

C

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

D

5-chloronicotinonitrile
51269-82-0

5-chloronicotinonitrile

Conditions
ConditionsYield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

chloroform
67-66-3

chloroform

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

C

2-cyano-5-chloropyridine
89809-64-3

2-cyano-5-chloropyridine

D

5-chloronicotinonitrile
51269-82-0

5-chloronicotinonitrile

Conditions
ConditionsYield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

chloroform
67-66-3

chloroform

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

C

5-chloronicotinonitrile
51269-82-0

5-chloronicotinonitrile

D

3-chloro-2-cyanopyridine
38180-46-0

3-chloro-2-cyanopyridine

Conditions
ConditionsYield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

chloroform
67-66-3

chloroform

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

C

5-chloronicotinonitrile
51269-82-0

5-chloronicotinonitrile

D

3-chloro-isonicotinonitrile
68325-15-5

3-chloro-isonicotinonitrile

Conditions
ConditionsYield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;
Pyrazin-N-Oxid(PyzNO)
2423-65-6

Pyrazin-N-Oxid(PyzNO)

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

2-Aminopyrazine
5049-61-6

2-Aminopyrazine

Conditions
ConditionsYield
With sodium hydroxide; trichlorophosphate 1) 70 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;
Pyrazin-N-Oxid(PyzNO)
2423-65-6

Pyrazin-N-Oxid(PyzNO)

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

1-(2-pyrazinyl) pyrazinium chloride

1-(2-pyrazinyl) pyrazinium chloride

Conditions
ConditionsYield
With trichlorophosphate at 70℃; for 2h; Product distribution;A 50 % Spectr.
B 50 % Spectr.
chloroform
67-66-3

chloroform

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

5-chloropyrimidine
17180-94-8

5-chloropyrimidine

Conditions
ConditionsYield
at 550℃; Yield given. Yields of byproduct given;
3-chloropyrazine 1-oxide
6863-76-9

3-chloropyrazine 1-oxide

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

2,5-dichloropyrazine
19745-07-4

2,5-dichloropyrazine

C

2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

D

2,6-dichloropyrazine
4774-14-5

2,6-dichloropyrazine

Conditions
ConditionsYield
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
2-chloropyrazine 1-oxide
16025-16-4

2-chloropyrazine 1-oxide

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

C

2,6-dichloropyrazine
4774-14-5

2,6-dichloropyrazine

Conditions
ConditionsYield
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
1,4-pyrazine
290-37-9

1,4-pyrazine

water
7732-18-5

water

chlorine
7782-50-5

chlorine

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

2,5-dichloropyrazine
19745-07-4

2,5-dichloropyrazine

C

2,3-dichloropyrazine
4858-85-9

2,3-dichloropyrazine

D

2,6-dichloropyrazine
4774-14-5

2,6-dichloropyrazine

Conditions
ConditionsYield
at 350℃; Product distribution;
CuCl(μ-2-chloropyrazine-N,N')
419581-31-0

CuCl(μ-2-chloropyrazine-N,N')

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(l) chloride

copper(l) chloride

Conditions
ConditionsYield
In neat (no solvent) heating in Ar at 220 °C; detected by powder X-ray diffractometry;
CuCl(μ-2-chloropyrazine-N,N')
419581-31-0

CuCl(μ-2-chloropyrazine-N,N')

oxygen
80937-33-3

oxygen

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(II) oxide

copper(II) oxide

Conditions
ConditionsYield
In neat (no solvent) in air, heating at 180 °C, CuCl, 2-chloropyrazine and some CuO were formed, Cu2OCl2 was formed at 392 °C, CuCl was formed again at430 °,C and CuO was formed in the last step at 461 °C; detected by X-ray powder diffractometry;
CuBr(μ-2-chloropyrazine-N,N')
419581-32-1

CuBr(μ-2-chloropyrazine-N,N')

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(I) bromide
7787-70-4

copper(I) bromide

Conditions
ConditionsYield
In neat (no solvent) heating in Ar at 200 °C; detected by powder X-ray diffractometry;
CuBr(μ-2-chloropyrazine-N,N')
419581-32-1

CuBr(μ-2-chloropyrazine-N,N')

oxygen
80937-33-3

oxygen

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(II) oxide

copper(II) oxide

Conditions
ConditionsYield
In neat (no solvent) in air, CuBr and 2-chloropyrazine were formed at 171 °C, CuBr wasoxidised during further heating; detected by X-ray powder diffractometry;
CuI(μ-2-chloropyrazine-N,N')
419581-33-2

CuI(μ-2-chloropyrazine-N,N')

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(l) iodide
7681-65-4

copper(l) iodide

Conditions
ConditionsYield
In neat (no solvent) heating in Ar at 150 °C; detected by powder X-ray diffractometry;
CuI(μ-2-chloropyrazine-N,N')
419581-33-2

CuI(μ-2-chloropyrazine-N,N')

oxygen
80937-33-3

oxygen

A

2-chloropyrazin
14508-49-7

2-chloropyrazin

B

copper(II) oxide

copper(II) oxide

Conditions
ConditionsYield
In neat (no solvent) in air, heating at 138 °C, Cu2I2(2-chloropyrazine) then CuI and 2-chloropyrazine were formed, CuO was formed in the last step around 340 °C; detected by X-ray powder diffractometry;
2-chloropyrazin
14508-49-7

2-chloropyrazin

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylpyrazine
29460-97-7

2-phenylpyrazine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; tricyclohexylphosphine; dichloro bis(acetonitrile) palladium(II) at 85 - 90℃; for 5h; Suzuki-Miyaura reaction;100%
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling;99%
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling;95%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2-mercaptopyrazine
38521-06-1

2-mercaptopyrazine

Conditions
ConditionsYield
With thiourea In ethanol for 16h; Reflux;100%
With hydrogen sulfide; sodium methylate In methanol for 1h; Heating;91%
With hydrogen sulfide; sodium ethanolate; N,N-dimethyl-formamide In ethanol at 100℃; for 3h;88%
2-chloropyrazin
14508-49-7

2-chloropyrazin

(2,3-dimethylphenyl)zinc chloride

(2,3-dimethylphenyl)zinc chloride

2-(2,3-dimethylphenyl)pyrazine

2-(2,3-dimethylphenyl)pyrazine

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 20℃; for 15h; Negishi coupling;100%
2-chloropyrazin
14508-49-7

2-chloropyrazin

methylamine
74-89-5

methylamine

N-methylpyrazin-2-amine
32111-28-7

N-methylpyrazin-2-amine

Conditions
ConditionsYield
at 100℃; for 15h;100%
In ethanol at 95℃; for 1h; Inert atmosphere; Sealed tube;77%
In dimethyl sulfoxide at 130℃;
2-chloropyrazin
14508-49-7

2-chloropyrazin

t-butyl 4-hydroxy piperidine-1-carboxylate
109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate
442199-08-8

t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;100%
In hexane; dimethyl sulfoxide; ethyl acetate
2-chloropyrazin
14508-49-7

2-chloropyrazin

(2,6-dimethylphenyl)magnesium bromide
21450-64-6

(2,6-dimethylphenyl)magnesium bromide

2-(2,6-dimethylphenyl)pyrazine
1157867-58-7

2-(2,6-dimethylphenyl)pyrazine

Conditions
ConditionsYield
Stage #1: (2,6-dimethylphenyl)magnesium bromide With dichloro(1,3-bis(2,6-bis(3-pentyl)phenyl)imidazolin-2-ylidene)(3-chloropyridyl)palladium(II); zinc(II) chloride In tetrahydrofuran at 23℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-chloropyrazin In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 23℃; for 24h; Negishi coupling; Inert atmosphere;
100%
2-chloropyrazin
14508-49-7

2-chloropyrazin

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

N,N'-dimethyl-N-pyrazin-2-yl-ethane-1,2-diamine

N,N'-dimethyl-N-pyrazin-2-yl-ethane-1,2-diamine

Conditions
ConditionsYield
In ethanol100%
2-chloropyrazin
14508-49-7

2-chloropyrazin

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

methyl pyrazine-2-carboxylate
6164-79-0

methyl pyrazine-2-carboxylate

Conditions
ConditionsYield
With dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); triethylamine at 100℃; under 2585.74 Torr; for 4h;99%
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In acetonitrile at 180℃; under 25502.6 Torr; Flow reactor;61%
With triethylamine; palladium bis(dibenzylideneacetone)palladium(0); triphenylphosphine at 120℃; under 29420.3 Torr; for 16h; other chloropyrazines;93 % Chromat.
With ethyl azide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) at 120℃; under 29420.3 Torr; for 16h;93 % Chromat.
2-chloropyrazin
14508-49-7

2-chloropyrazin

phenylacetylene
536-74-3

phenylacetylene

2-(2-phenylethynyl)pyrazine
96129-41-8

2-(2-phenylethynyl)pyrazine

Conditions
ConditionsYield
With potassium phosphate; bis[dicyclohexyl(2,4,6-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane]palladium(II) dichloride In acetonitrile at 90℃; for 6h; Sonogashira Cross-Coupling;99%
With tetrabutylammomium bromide; potassium carbonate; triphenylphosphine; copper(I) oxide at 135 - 140℃; for 24h; Sonogashira coupling;98%
With bis(η3-allyl-μ-chloropalladium(II)); triethylamine; triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 4h; Heck alkynylation; Inert atmosphere;95%
With dichloro bis(acetonitrile) palladium(II); 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; caesium carbonate In water; acetonitrile at 100℃; for 24h; Sonogashira Cross-Coupling;89%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 70℃; for 12h; Sonogashira coupling;76%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2,6-dimethylbenzene boronic acid
100379-00-8

2,6-dimethylbenzene boronic acid

2-(2,6-dimethylphenyl)pyrazine
1157867-58-7

2-(2,6-dimethylphenyl)pyrazine

Conditions
ConditionsYield
With trans-dichloro(1,3-bis-(2,6-diisopentylphenyl)imidazolylidinium)(3-chloro-pyridine); potassium tert-butylate In tert-butyl alcohol at 65℃; Suzuki-Miyaura coupling; Inert atmosphere; Molecular sieve;99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-(4-methylphenyl)pyrazine
108030-80-4

2-(4-methylphenyl)pyrazine

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 0.333333h; Suzuki coupling;99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; tetrabutylammomium bromide; sodium hydrogencarbonate In water for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Reflux;98%
Stage #1: 2-chloropyrazin; 4-methylphenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 95℃; for 0.166667h; Suzuki Coupling; Inert atmosphere;
Stage #2: With potassium fluoride dihydrate In water; toluene at 95℃; Suzuki Coupling; Inert atmosphere;
96%
With potassium phosphate tribasic heptahydrate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 24h; Suzuki cross-coupling reaction;88%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.666667h; Suzuki coupling;82%
6-methyl-2-pyridylzinc bromide

6-methyl-2-pyridylzinc bromide

2-chloropyrazin
14508-49-7

2-chloropyrazin

6-Methyl-2-(2-pyrazinyl)pyridine
149775-45-1

6-Methyl-2-(2-pyrazinyl)pyridine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 3h; Negishi cross-coupling; Inert atmosphere;99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2-Methoxyphenylboronic acid
5720-06-9

2-Methoxyphenylboronic acid

2-(2-methoxyphenyl)pyrazine
251933-26-3

2-(2-methoxyphenyl)pyrazine

Conditions
ConditionsYield
With (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 3h; Catalytic behavior; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;99%
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling;91%
2-chloropyrazin
14508-49-7

2-chloropyrazin

3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

2-(3-methoxyphenyl)-pyrazine
912771-38-1

2-(3-methoxyphenyl)-pyrazine

Conditions
ConditionsYield
Stage #1: 2-chloropyrazin; 3-methoxyphenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 95℃; for 0.166667h; Suzuki Coupling; Inert atmosphere;
Stage #2: With potassium fluoride dihydrate In water; toluene at 95℃; Suzuki Coupling; Inert atmosphere;
99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

4-fluoro-2-methylphenylboronic acid
139911-29-8

4-fluoro-2-methylphenylboronic acid

2-(4-fluoro-2-methylphenyl)pyrazine
334476-87-8

2-(4-fluoro-2-methylphenyl)pyrazine

Conditions
ConditionsYield
Stage #1: 2-chloropyrazin; 4-fluoro-2-methylphenylboronic acid With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 95℃; for 0.166667h; Suzuki Coupling; Inert atmosphere;
Stage #2: With potassium fluoride dihydrate In water; toluene at 95℃; Suzuki Coupling; Inert atmosphere;
99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

2-(4-methoxybenzyloxy)pyrazine

2-(4-methoxybenzyloxy)pyrazine

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzyl alcohol With sodium hydride In 1,2-dimethoxyethane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 2-chloropyrazin In 1,2-dimethoxyethane at 0 - 45℃; Inert atmosphere;
99%
2-chloropyrazin
14508-49-7

2-chloropyrazin

ferrous(II) sulfate heptahydrate

ferrous(II) sulfate heptahydrate

potassium thioacyanate
333-20-0

potassium thioacyanate

Fe(NCS)2(2-chloropyrazine)4

Fe(NCS)2(2-chloropyrazine)4

Conditions
ConditionsYield
In water at 20℃; for 24h;98.6%
2-chloropyrazin
14508-49-7

2-chloropyrazin

nickel(II) thiocyanate
13689-92-4

nickel(II) thiocyanate

Ni(NCS)2(2-chloropyrazine)4·2-chloropyrazine solvate

Ni(NCS)2(2-chloropyrazine)4·2-chloropyrazine solvate

Conditions
ConditionsYield
at 20℃; for 72h;98.5%
2-chloropyrazin
14508-49-7

2-chloropyrazin

nickel(II) thiocyanate
13689-92-4

nickel(II) thiocyanate

[Ni(NCS)2(2-chloropyrazine)2]n

[Ni(NCS)2(2-chloropyrazine)2]n

Conditions
ConditionsYield
In acetonitrile at 20℃; for 168h;98.3%
2-chloropyrazin
14508-49-7

2-chloropyrazin

potassium enolate of acetone
128190-66-9, 25088-58-8

potassium enolate of acetone

1-(pyrazin-2-yl)propan-2-one
6784-62-9

1-(pyrazin-2-yl)propan-2-one

Conditions
ConditionsYield
In diethyl ether; ammonia for 0.25h; Mechanism; Product distribution; effect of inhibitor (di-tert-butyl-nitroxide);98%
2-chloropyrazin
14508-49-7

2-chloropyrazin

3-(Tributylstannyl)pyridine N-oxide

3-(Tributylstannyl)pyridine N-oxide

3-(2-Pyrazinyl)pyridine N-oxide

3-(2-Pyrazinyl)pyridine N-oxide

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 36h; Heating;98%
2-chloropyrazin
14508-49-7

2-chloropyrazin

thiophene boronic acid
6165-68-0

thiophene boronic acid

2-(thiophen-2-yl)pyrazine
56421-72-8

2-(thiophen-2-yl)pyrazine

Conditions
ConditionsYield
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling;98%
With tetrabutyl ammonium fluoride; tricyclohexylphosphine; dichloro bis(acetonitrile) palladium(II) at 85 - 90℃; for 5h; Suzuki-Miyaura reaction;95%
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling;87%
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 160℃; for 0.5h; Suzuki Coupling; Microwave irradiation;71%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium hydroxide; palladium diacetate In N,N-dimethyl-formamide at 110℃; for 38h; Suzuki-Miyaura cross-coupling;50%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2-(tri-n-butylstannyl)thiazole
121359-48-6

2-(tri-n-butylstannyl)thiazole

2-(2'-pyrazinyl)thiazole

2-(2'-pyrazinyl)thiazole

Conditions
ConditionsYield
With trans-dichloro(1,3-bis-(2,6-diisopentylphenyl)imidazolylidinium)(3-chloro-pyridine); cesium fluoride In 1,4-dioxane at 20 - 80℃; for 32h; Stille-Migita cross-coupling; Molecular sieve; Inert atmosphere;98%
2-chloropyrazin
14508-49-7

2-chloropyrazin

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2-(4-fluorophenyl)pyrazine
939975-25-4

2-(4-fluorophenyl)pyrazine

Conditions
ConditionsYield
Stage #1: 2-chloropyrazin; 4-fluoroboronic acid With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 95℃; for 0.166667h; Suzuki Coupling; Inert atmosphere;
Stage #2: With potassium fluoride dihydrate In water; toluene at 95℃; Suzuki Coupling; Inert atmosphere;
98%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.5h; Suzuki Coupling;90%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 1.58333h; Suzuki coupling;88%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2-(2-methylphenyl)pyrazine
87537-41-5

2-(2-methylphenyl)pyrazine

Conditions
ConditionsYield
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling;98%
With 2-((3-sulfonatomesityl)-5-sulfonatoindenyl)dicyclohexylphosphinehydrate sodium salt; palladium diacetate; potassium carbonate In water at 100℃; for 24h; Suzuki-Miyaura Coupling;90%
2-chloropyrazin
14508-49-7

2-chloropyrazin

m-tolylboronic acid
17933-03-8

m-tolylboronic acid

2-(3-methylphenyl)pyrazine
1142346-68-6

2-(3-methylphenyl)pyrazine

Conditions
ConditionsYield
Stage #1: 2-chloropyrazin; m-tolylboronic acid With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 95℃; for 0.166667h; Suzuki Coupling; Inert atmosphere;
Stage #2: With potassium fluoride dihydrate In water; toluene at 95℃; Suzuki Coupling; Inert atmosphere;
98%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 80℃; for 2.5h; Inert atmosphere;95%
With potassium phosphate tribasic trihydrate; C30H39P; palladium diacetate In tetrahydrofuran at 110℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere;93%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 80℃; for 2.5h;
2-chloropyrazin
14508-49-7

2-chloropyrazin

Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

2-(thiophen-3-yl)pyrazine
56421-87-5

2-(thiophen-3-yl)pyrazine

Conditions
ConditionsYield
With C84H64Cl3N3Pd; potassium carbonate In ethanol at 80℃; for 2h; Suzuki-Miyaura Coupling;98%
With potassium phosphate; C46H52Cl3N3O2Pd In tetrahydrofuran; water at 60℃; for 4h; Suzuki-Miyaura Coupling;91%
2-chloropyrazin
14508-49-7

2-chloropyrazin

nickel(II) thiocyanate
13689-92-4

nickel(II) thiocyanate

Ni(NCS)2(2-chloropyrazine)4

Ni(NCS)2(2-chloropyrazine)4

Conditions
ConditionsYield
In water at 20℃; for 48h;97.6%
2-chloropyrazin
14508-49-7

2-chloropyrazin

thiophenol
108-98-5

thiophenol

2-(phenylsulfanyl)pyrazine
107697-83-6

2-(phenylsulfanyl)pyrazine

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;97%
at 28℃; for 12h;94%
Stage #1: 2-chloropyrazin 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: thiophenol With potassium phosphate In N,N-dimethyl-formamide at 50℃; for 2h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Schlenk technique; Inert atmosphere;
88%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 120℃; for 17h;86%
With sodium hydride In dimethyl sulfoxide for 5h; Heating;70%
2-chloropyrazin
14508-49-7

2-chloropyrazin

2,2'-bipyrazine
10199-00-5

2,2'-bipyrazine

Conditions
ConditionsYield
With palladium diacetate; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine In isopropyl alcohol; toluene at 105℃; for 24h;97%
With potassium hydroxide In water; N,N-dimethyl-formamide at 35℃; for 12h; Ullmann Condensation; Inert atmosphere;94%
With nickel diacetate; triphenylphosphine; sodium t-butanolate In 1,2-dimethoxyethane at 45℃; for 0.00277778h;48%
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 16h;42%
With palladium diacetate; potassium carbonate In isopropyl alcohol; toluene at 100℃; for 5h; Reagent/catalyst; Inert atmosphere;3%

2-Chloropyrazine Chemical Properties

Molecular Structure of 2-Chloropyrazine (CAS NO.14508-49-7):

IUPAC Name: 2-Chloropyrazine
Molecular Formula: C4H3ClN2
Molecular Weight: 114.53 g/mol
Density: 1.303 g/cm3
Flash Point: 57.8 °C
Boiling Point: 155.3 °C at 760 mmHg 
Water Solubility: insoluble
Index of Refraction: 1.534
Molar Refractivity: 27.33 cm3
Molar Volume: 87.8 cm3
Surface Tension: 48.2 dyne/cm 
XLogP3: 0.7
H-Bond Acceptor: 2
Exact Mass: 113.998476
MonoIsotopic Mass: 113.998476
Topological Polar Surface Area: 25.8
Heavy Atom Count: 7 
Canonical SMILES: C1=CN=C(C=N1)Cl
InChI: InChI=1S/C4H3ClN2/c5-4-3-6-1-2-7-4/h1-3H
InChIKey: GELVZYOEQVJIRR-UHFFFAOYSA-N
EINECS: 238-517-0
Product Categories: Halides; Heterocycles; Pyrazines; Pyrazine; Chloropyrazines, etc.; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; PyrazinesHeterocyclic Building Blocks 

2-Chloropyrazine Uses

 2-Chloropyrazine (CAS NO.14508-49-7) is used as intermediates of medicine and pesticide.

2-Chloropyrazine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: UN 1993 3/PG 3
WGK Germany: 3
Hazard Note: Irritant
TSCA: T
HazardClass: 3
PackingGroup: III
HS Code: 29339990

2-Chloropyrazine Specification

 2-Chloropyrazine (CAS NO.14508-49-7) is also named as Chloropyrazine ; Pyrazine, 2-chloro- ; Pyrazine, chloro- . 2-Chloropyrazine (CAS NO.14508-49-7) is clear colorless to yellowish liquid.

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