14508-49-7

Basic information

• Product Name: 2-Chloropyrazine
• Synonyms: 2-Dichloropyrazine;chloro-pyrazin;Pyrazine, chloro-;2-CHLOROPYRAZINE;CHLOROPYRAZINE;CHLOROPYRAZINE, 2-;CHLOROPYRAZINE, 2-(SG);2-chloropyrazine(SALTDATA: FREE)
• CAS NO: 14508-49-7
• Molecular Formula: C₄H₃ClN₂
• Molecular Weight: 114.53
• EINECS: 238-517-0
• Product Categories: Halides;Heterocycles;Pyrazines;Pyrazine;Chloropyrazines, etc.;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrazinesHeterocyclic Building Blocks;API Intermediate;NULL;alkyl chloride;Pesticides intermediate;Inhibitors
• Mol File: 14508-49-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 153～154℃
• Boiling Point: 153-154 °C(lit.)
• Flash Point: 136 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.283 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.92mmHg at 25°C
• Refractive Index: n20/D 1.539(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in Methanol
• PKA: -1.10±0.10(Predicted)
• Water Solubility: INSOLUBLE
• BRN: 107019
• CAS DataBase Reference: 2-Chloropyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropyrazine(14508-49-7)
• EPA Substance Registry System: 2-Chloropyrazine(14508-49-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 14508-49-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellowish liquid

Uses

2-Chloropyrazine is used in cardiotonic, in biological, drug, flavoring and perfumery industry.

Application

2-Chloropyrazine is used as a reagent in the synthesis of hetaryloxy benzoxaborole compounds which have antimalarial activity. 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.

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.]

InChI:InChI=1/C4H3ClN2/c5-4-3-6-1-2-7-4/h1-3H

Synthetic route

2-hydroxypyrazine sodium salt (24387-68-6) → 2-chloropyrazin (14508-49-7)

Conditions	Yield
With thionyl chloride; N-ethyl-N,N-diisopropylamine In chloroform at 65℃; for 2h; Reagent/catalyst;	95.4%

pyrazin-2-ol (6270-63-9) → 2-chloropyrazin (14508-49-7)

Conditions	Yield
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-chloropyrazin (14508-49-7)

Conditions	Yield
With thionyl chloride In pyridine; para-tert-butylphenol; benzene	75%

Pyrazin-N-Oxid(PyzNO) (2423-65-6) → 2-chloropyrazin (14508-49-7)

Conditions	Yield
With trichlorophosphate at 70℃; for 2h;	37%
With trichlorophosphate	35%

Pyrazin-N-Oxid(PyzNO) (2423-65-6) → 2-chloropyrazin (14508-49-7) + Pyrazine 1-oxide; hydrochloride + 1-(2-pyrazinyl) pyrazinium salt

Conditions	Yield
With trichlorophosphate for 0.5h; Product distribution; Ambient temperature;	A 13% B 30% C n/a

1,4-pyrazine (290-37-9) → 2-chloropyrazin (14508-49-7)

Conditions	Yield
With chlorine at 500℃;
With water; chlorine at 450℃;

pyrazin-2(1H)-one (6270-63-9) → 2-chloropyrazin (14508-49-7)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate
With trichlorophosphate

1H-imidazole (288-32-4) + chloroform (67-66-3) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8)

Conditions	Yield
at 550℃; Yield given. Yields of byproduct given;

1-methyl-1H-imidazole (616-47-7) + chloroform (67-66-3) → 2-chloropyrazin (14508-49-7) + 1H-pyrrole-2-carbonitrile (4513-94-4) + 5-chloropyrimidine (17180-94-8) + 5-chloronicotinonitrile (51269-82-0)

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;

1-methyl-1H-imidazole (616-47-7) + chloroform (67-66-3) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8) + 2-cyano-5-chloropyridine (89809-64-3) + 5-chloronicotinonitrile (51269-82-0)

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;

1-methyl-1H-imidazole (616-47-7) + chloroform (67-66-3) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8) + 5-chloronicotinonitrile (51269-82-0) + 3-chloro-2-cyanopyridine (38180-46-0)

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;

1-methyl-1H-imidazole (616-47-7) + chloroform (67-66-3) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8) + 5-chloronicotinonitrile (51269-82-0) + 3-chloro-isonicotinonitrile (68325-15-5)

Conditions	Yield
at 550℃; Yield given. Further byproducts given. Yields of byproduct given;

Pyrazin-N-Oxid(PyzNO) (2423-65-6) → 2-chloropyrazin (14508-49-7) + 2-Aminopyrazine (5049-61-6)

Conditions	Yield
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) → 2-chloropyrazin (14508-49-7) + 1-(2-pyrazinyl) pyrazinium chloride

Conditions	Yield
With trichlorophosphate at 70℃; for 2h; Product distribution;	A 50 % Spectr. B 50 % Spectr.

chloroform (67-66-3) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 2-chloropyrazin (14508-49-7) + 5-chloropyrimidine (17180-94-8)

Conditions	Yield
at 550℃; Yield given. Yields of byproduct given;

3-chloropyrazine 1-oxide (6863-76-9) → 2-chloropyrazin (14508-49-7) + 2,5-dichloropyrazine (19745-07-4) + 2,3-dichloropyrazine (4858-85-9) + 2,6-dichloropyrazine (4774-14-5)

Conditions	Yield
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-chloropyrazin (14508-49-7) + 2,3-dichloropyrazine (4858-85-9) + 2,6-dichloropyrazine (4774-14-5)

Conditions	Yield
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1,4-pyrazine (290-37-9) + water (7732-18-5) + chlorine (7782-50-5) → 2-chloropyrazin (14508-49-7) + 2,5-dichloropyrazine (19745-07-4) + 2,3-dichloropyrazine (4858-85-9) + 2,6-dichloropyrazine (4774-14-5)

Conditions	Yield
at 350℃; Product distribution;

CuCl(μ-2-chloropyrazine-N,N') (419581-31-0) → 2-chloropyrazin (14508-49-7) + copper(l) chloride

Conditions	Yield
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) + oxygen (80937-33-3) → 2-chloropyrazin (14508-49-7) + copper(II) oxide

Conditions	Yield
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) → 2-chloropyrazin (14508-49-7) + copper(I) bromide (7787-70-4)

Conditions	Yield
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) + oxygen (80937-33-3) → 2-chloropyrazin (14508-49-7) + copper(II) oxide

Conditions	Yield
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) → 2-chloropyrazin (14508-49-7) + copper(l) iodide (7681-65-4)

Conditions	Yield
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) + oxygen (80937-33-3) → 2-chloropyrazin (14508-49-7) + copper(II) oxide

Conditions	Yield
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) + phenylboronic acid (98-80-6) → 2-phenylpyrazine (29460-97-7)

Conditions	Yield
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-mercaptopyrazine (38521-06-1)

Conditions	Yield
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) + (2,3-dimethylphenyl)zinc chloride → 2-(2,3-dimethylphenyl)pyrazine

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 20℃; for 15h; Negishi coupling;	100%

2-chloropyrazin (14508-49-7) + methylamine (74-89-5) → N-methylpyrazin-2-amine (32111-28-7)

Conditions	Yield
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) + t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate (442199-08-8)

Conditions	Yield
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) + (2,6-dimethylphenyl)magnesium bromide (21450-64-6) → 2-(2,6-dimethylphenyl)pyrazine (1157867-58-7)

Conditions	Yield
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) + N,N`-dimethylethylenediamine (110-70-3) → N,N'-dimethyl-N-pyrazin-2-yl-ethane-1,2-diamine

Conditions	Yield
In ethanol	100%

2-chloropyrazin (14508-49-7) + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl pyrazine-2-carboxylate (6164-79-0)

Conditions	Yield
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) + phenylacetylene (536-74-3) → 2-(2-phenylethynyl)pyrazine (96129-41-8)

Conditions	Yield
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) + 2,6-dimethylbenzene boronic acid (100379-00-8) → 2-(2,6-dimethylphenyl)pyrazine (1157867-58-7)

Conditions	Yield
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) + 4-methylphenylboronic acid (5720-05-8) → 2-(4-methylphenyl)pyrazine (108030-80-4)

Conditions	Yield
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 + 2-chloropyrazin (14508-49-7) → 6-Methyl-2-(2-pyrazinyl)pyridine (149775-45-1)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 3h; Negishi cross-coupling; Inert atmosphere;	99%

2-chloropyrazin (14508-49-7) + 2-Methoxyphenylboronic acid (5720-06-9) → 2-(2-methoxyphenyl)pyrazine (251933-26-3)

Conditions	Yield
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) + 3-methoxyphenylboronic acid (10365-98-7) → 2-(3-methoxyphenyl)-pyrazine (912771-38-1)

Conditions	Yield
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) + 4-fluoro-2-methylphenylboronic acid (139911-29-8) → 2-(4-fluoro-2-methylphenyl)pyrazine (334476-87-8)

Conditions	Yield
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) + 4-Methoxybenzyl alcohol (105-13-5) → 2-(4-methoxybenzyloxy)pyrazine

Conditions	Yield
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) + ferrous(II) sulfate heptahydrate + potassium thioacyanate (333-20-0) → Fe(NCS)2(2-chloropyrazine)4

Conditions	Yield
In water at 20℃; for 24h;	98.6%

2-chloropyrazin (14508-49-7) + nickel(II) thiocyanate (13689-92-4) → Ni(NCS)2(2-chloropyrazine)4·2-chloropyrazine solvate

Conditions	Yield
at 20℃; for 72h;	98.5%

2-chloropyrazin (14508-49-7) + nickel(II) thiocyanate (13689-92-4) → [Ni(NCS)2(2-chloropyrazine)2]n

Conditions	Yield
In acetonitrile at 20℃; for 168h;	98.3%

2-chloropyrazin (14508-49-7) + potassium enolate of acetone (128190-66-9, 25088-58-8) → 1-(pyrazin-2-yl)propan-2-one (6784-62-9)

Conditions	Yield
In diethyl ether; ammonia for 0.25h; Mechanism; Product distribution; effect of inhibitor (di-tert-butyl-nitroxide);	98%

2-chloropyrazin (14508-49-7) + 3-(Tributylstannyl)pyridine N-oxide → 3-(2-Pyrazinyl)pyridine N-oxide

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 36h; Heating;	98%

2-chloropyrazin (14508-49-7) + thiophene boronic acid (6165-68-0) → 2-(thiophen-2-yl)pyrazine (56421-72-8)

Conditions	Yield
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-(tri-n-butylstannyl)thiazole (121359-48-6) → 2-(2'-pyrazinyl)thiazole

Conditions	Yield
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) + 4-fluoroboronic acid (1765-93-1) → 2-(4-fluorophenyl)pyrazine (939975-25-4)

Conditions	Yield
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-Methylphenylboronic acid (16419-60-6) → 2-(2-methylphenyl)pyrazine (87537-41-5)

Conditions	Yield
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) + m-tolylboronic acid (17933-03-8) → 2-(3-methylphenyl)pyrazine (1142346-68-6)

Conditions	Yield
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) + Thien-3-ylboronic acid (6165-69-1) → 2-(thiophen-3-yl)pyrazine (56421-87-5)

Conditions	Yield
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) + nickel(II) thiocyanate (13689-92-4) → Ni(NCS)2(2-chloropyrazine)4

Conditions	Yield
In water at 20℃; for 48h;	97.6%

2-chloropyrazin (14508-49-7) + thiophenol (108-98-5) → 2-(phenylsulfanyl)pyrazine (107697-83-6)

Conditions	Yield
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) → 2,2'-bipyrazine (10199-00-5)

Conditions	Yield
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%

Upstream product

• 288-32-4 1H-imidazole 
• 67-66-3 chloroform 
• 616-47-7 1-methyl-1H-imidazole 
• 290-37-9 1,4-pyrazine 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 24387-68-6 2-hydroxypyrazine sodium salt 
• 16025-16-4 2-chloropyrazine 1-oxide 
• 6863-76-9 3-chloropyrazine 1-oxide 
• 6270-63-9 pyrazin-2-ol 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 2423-65-6 Pyrazin-N-Oxid(PyzNO) 
• 6270-63-9 pyrazin-2(1H)-one 
• 419581-33-2 CuI(μ-2-chloropyrazine-N,N') 

Downstream Products

• 34803-68-4 1-(pyrazin-2-yl)piperazine 
• 3149-28-8 2-methoxypyrazine 
• 38028-67-0 2-ethoxypyrazine 
• 107697-82-5 (Pyrazine-2-yloxy)benzene 
• 146374-16-5 3-amino-benzenesulfonic acid pyrazin-2-ylamide 
• 116-44-9 sulfapyrazine 
• 326-02-3 3-chloro-1-(4-fluoro-phenacyl)-pyrazinium; bromide 
• 6270-63-9 pyrazin-2(1H)-one 
• 38521-06-1 2(1H)-pyrazinethione 
• 38521-09-4 bis(pyrazin-2-yl)sulfane 
• 5049-61-6 2-Aminopyrazine 
• 4774-14-5 2,6-dichloropyrazine 
• 5049-62-7 sodium pyrazine-2-sulfonate 
• 159470-80-1 2-(diphenylmethyleneamino)-2-(pyrazin-2-yl)acetic acid ethyl ester 

Relevant 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)]

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

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Efficient Phosphorus-Free Chlorination of Hydroxy Aza-Arenes and Their Application in One-Pot Pharmaceutical Synthesis

The chlorination of hydroxy aza-arenes with bis(trichloromethyl) carbonate (BTC) and SOCl2 has been effectively performed by refluxing with 5 wt % 4-dimethylaminopyridine (DMAP) as a catalyst. Various substrates are chlorinated with high yields. The obtained chlorinated aza-arenes can be used directly with simple workup for succedent one-pot synthesis on a large scale.

Pyrazinoic acid esters as antituberculosis agents

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.