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14508-49-7

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14508-49-7 Usage

Description

2-Chloropyrazine is a clear colorless to yellowish liquid with various applications across different industries due to its unique chemical properties.

Uses

Used in Cardiotonic Applications:
2-Chloropyrazine is used as a cardiotonic agent, which helps to strengthen the contraction of the heart muscle, improving the overall efficiency of the heart's function.
Used in Biological Industry:
In the biological industry, 2-Chloropyrazine is utilized as a reagent in the synthesis of various compounds, contributing to the development of new biological products and research.
Used in Drug Industry:
2-Chloropyrazine is used as a reagent in the synthesis of hetaryloxy benzoxaborole compounds, which possess antimalarial activity, playing a crucial role in the development of new drugs to combat malaria.
Used in Flavoring and Perfumery Industry:
2-Chloropyrazine is employed in the flavoring and perfumery industry for its unique properties that contribute to the creation of various scents and flavors.
Used in Synthesis of Serine β-Lactamase Inhibitors:
2-Chloropyrazine is also used to prepare 4,5-disubstituted 6-aryloxy-1,3-dihydrobenzo[c][1,2]oxaboroles, which are broad-spectrum serine β-lactamase inhibitors. These inhibitors are essential in the development of new antibiotics to combat antibiotic-resistant bacteria.

Purification Methods

Fractionally distil it through a short column packed with glass helices. It has apenetrating, mildly pungent odour with a high vapour pressure at room temperature. [Erickson & Spoerri J Am Chem Soc 68 400 1946, Hetman & O.Donnell J Org Chem 28 1682 1963, Beilstein 23/5 V 366.]

Check Digit Verification of cas no

The CAS Registry Mumber 14508-49-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,0 and 8 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 14508-49:
(7*1)+(6*4)+(5*5)+(4*0)+(3*8)+(2*4)+(1*9)=97
97 % 10 = 7
So 14508-49-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H3ClN2/c5-4-3-6-1-2-7-4/h1-3H

14508-49-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A10108)  2-Chloropyrazine, 98%   

  • 14508-49-7

  • 5g

  • 288.0CNY

  • Detail
  • Alfa Aesar

  • (A10108)  2-Chloropyrazine, 98%   

  • 14508-49-7

  • 10g

  • 489.0CNY

  • Detail
  • Alfa Aesar

  • (A10108)  2-Chloropyrazine, 98%   

  • 14508-49-7

  • 25g

  • 967.0CNY

  • Detail
  • Alfa Aesar

  • (A10108)  2-Chloropyrazine, 98%   

  • 14508-49-7

  • 100g

  • 3482.0CNY

  • Detail
  • Aldrich

  • (132489)  2-Chloropyrazine  97%

  • 14508-49-7

  • 132489-5G

  • 313.56CNY

  • Detail
  • Aldrich

  • (132489)  2-Chloropyrazine  97%

  • 14508-49-7

  • 132489-25G

  • 1,055.34CNY

  • Detail

14508-49-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloropyrazine

1.2 Other means of identification

Product number -
Other names 2-chloro-1,4-pyrazine

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:14508-49-7 SDS

14508-49-7Synthetic 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%

14508-49-7Relevant articles and documents

Synthesis, crystal structures, and properties of the copper(I) halide coordination polymers ∞2[CuX(μ-2-chloropyrazine-N,N′)] (X = Cl, Br), ∞1[CuI(2-chloropyrazine-N)], and [Cu2I2(2-chloropyrazine)]

Naether, Christian,Wriedt, Mario,Je, Inke

, p. 394 - 400 (2002)

The new copper coordination polymers ∞2[CuX(μ-2-chloropyrazine-N,N′)] (X = Cl (I), Br (II), ∞1[CuI(2-chloropyrazine-N)] (III) and [Cu2I2(2-chloropyrazine)] (IV) has been prepared by the reaction of the copper(I) halides with 2-chloropyrazine at room-temperature or under hydrothermal conditions. The crystal structures of the 1:1 compounds I and II consist of zig-zag CuX single chains running parallel to the crystallographic a-axis which are linked by the 2-chloropyrazine spacer molecules to sheets parallel to (010). For the iodine compound III a one-dimensional structure is Found which consists of CuX double chains running parallel to the crystallographic a-axis. The thermic properties of all compounds were investigated in different gas atmospheres using simultaneously differential thermal analysis and thermogravimetry (DTA-TG) as well as temperature resolved X-ray powder diffraction. On heating, tire 1:1 compounds I and II decompose directly to the corresponding copper(I) Halides, whereas the thermal decomposition of III occcur via IV as an intermediate.

Studies on Pyrazines. 11. A Novel Formation of 2-Aminopyrazine from the Reaction of Pyrazine 1-Oxide with Phosphoryl Chloride

Sato, Nobuhiro,Kobayashi, Michio

, p. 3015 - 3016 (1984)

-

-

Cheeseman

, p. 242,246 (1960)

-

Preparation method of 2, 6-dichloropyrazine

-

Paragraph 0034; 0038-0039; 0047-0052, (2020/04/22)

The invention discloses a preparation method of 2, 6-dichloropyrazine. The method comprises the following steps: taking glycine and glyoxal as raw materials, carrying out ammoniation and cyclization reactions to prepare 2-hydroxypyrazine sodium; and reacting 2-hydroxypyrazine sodium with thionyl chloride under the catalytic action of N,N-diisopropylethylamine to prepare 2-chloropyrazine; wherein pyridine is used as a solvent, and 2-chloropyrazine is subjected to chlorination of chlorine to obtain 2,6-dichloropyrazine. The method has the advantages that the raw material namely glycine is cheapand easily available, and phosphorus oxychloride is not used as a chlorination reagent, so that the generation of organic phosphorus-containing wastewater is greatly reduced, and an effective way is provided for efficient green industrial production of 2, 6-dichloropyrazine.

Pyrazinoic acid esters as antituberculosis agents

-

, (2008/06/13)

Pyrazinoic esters have been prepared. Compounds of this group are effective against mycobacteria including Mycobacteria tuberculosis, pyrazinamide-resistant Mycobacteria tuberculosis, Mycobacteria bovis and Mycobacteria kansasii.

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