2-hydroxypyrazine sodium salt
2-chloropyrazin
Conditions | Yield |
---|---|
With thionyl chloride; N-ethyl-N,N-diisopropylamine In chloroform at 65℃; for 2h; Reagent/catalyst; | 95.4% |
pyrazin-2-ol
2-chloropyrazin
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
2-chloropyrazin
Conditions | Yield |
---|---|
With thionyl chloride In pyridine; para-tert-butylphenol; benzene | 75% |
Pyrazin-N-Oxid(PyzNO)
2-chloropyrazin
Conditions | Yield |
---|---|
With trichlorophosphate at 70℃; for 2h; | 37% |
With trichlorophosphate | 35% |
Pyrazin-N-Oxid(PyzNO)
A
2-chloropyrazin
Conditions | Yield |
---|---|
With trichlorophosphate for 0.5h; Product distribution; Ambient temperature; | A 13% B 30% C n/a |
1,4-pyrazine
2-chloropyrazin
Conditions | Yield |
---|---|
With chlorine at 500℃; | |
With water; chlorine at 450℃; |
pyrazin-2(1H)-one
2-chloropyrazin
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate | |
With trichlorophosphate |
1H-imidazole
chloroform
A
2-chloropyrazin
B
5-chloropyrimidine
Conditions | Yield |
---|---|
at 550℃; Yield given. Yields of byproduct given; |
1-methyl-1H-imidazole
chloroform
A
2-chloropyrazin
B
1H-pyrrole-2-carbonitrile
C
5-chloropyrimidine
D
5-chloronicotinonitrile
Conditions | Yield |
---|---|
at 550℃; Yield given. Further byproducts given. Yields of byproduct given; |
1-methyl-1H-imidazole
chloroform
A
2-chloropyrazin
B
5-chloropyrimidine
C
2-cyano-5-chloropyridine
D
5-chloronicotinonitrile
Conditions | Yield |
---|---|
at 550℃; Yield given. Further byproducts given. Yields of byproduct given; |
1-methyl-1H-imidazole
chloroform
A
2-chloropyrazin
B
5-chloropyrimidine
C
5-chloronicotinonitrile
D
3-chloro-2-cyanopyridine
Conditions | Yield |
---|---|
at 550℃; Yield given. Further byproducts given. Yields of byproduct given; |
1-methyl-1H-imidazole
chloroform
A
2-chloropyrazin
B
5-chloropyrimidine
C
5-chloronicotinonitrile
D
3-chloro-isonicotinonitrile
Conditions | Yield |
---|---|
at 550℃; Yield given. Further byproducts given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sodium hydroxide; trichlorophosphate 1) 70 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With trichlorophosphate at 70℃; for 2h; Product distribution; | A 50 % Spectr. B 50 % Spectr. |
chloroform
1-(Trimethylsilyl)imidazole
A
2-chloropyrazin
B
5-chloropyrimidine
Conditions | Yield |
---|---|
at 550℃; Yield given. Yields of byproduct given; |
3-chloropyrazine 1-oxide
A
2-chloropyrazin
B
2,5-dichloropyrazine
C
2,3-dichloropyrazine
D
2,6-dichloropyrazine
Conditions | Yield |
---|---|
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
2-chloropyrazine 1-oxide
A
2-chloropyrazin
B
2,3-dichloropyrazine
C
2,6-dichloropyrazine
Conditions | Yield |
---|---|
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
1,4-pyrazine
water
chlorine
A
2-chloropyrazin
B
2,5-dichloropyrazine
C
2,3-dichloropyrazine
D
2,6-dichloropyrazine
Conditions | Yield |
---|---|
at 350℃; Product distribution; |
Conditions | Yield |
---|---|
In neat (no solvent) heating in Ar at 220 °C; detected by powder X-ray diffractometry; |
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')
A
2-chloropyrazin
B
copper(I) bromide
Conditions | Yield |
---|---|
In neat (no solvent) heating in Ar at 200 °C; detected by powder X-ray diffractometry; |
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; |
Conditions | Yield |
---|---|
In neat (no solvent) heating in Ar at 150 °C; detected by powder X-ray diffractometry; |
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; |
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
2-mercaptopyrazine
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% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 20℃; for 15h; Negishi coupling; | 100% |
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
t-butyl 4-hydroxy piperidine-1-carboxylate
t-butyl 4-[(pyrazin-2-yl)oxy]piperidine-1-carboxylate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 100% |
In hexane; dimethyl sulfoxide; ethyl acetate |
2-chloropyrazin
(2,6-dimethylphenyl)magnesium bromide
2-(2,6-dimethylphenyl)pyrazine
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
N,N`-dimethylethylenediamine
Conditions | Yield |
---|---|
In ethanol | 100% |
2-chloropyrazin
methanol
carbon monoxide
methyl pyrazine-2-carboxylate
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. |
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
2,6-dimethylbenzene boronic acid
2-(2,6-dimethylphenyl)pyrazine
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
4-methylphenylboronic acid
2-(4-methylphenyl)pyrazine
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% |
2-chloropyrazin
6-Methyl-2-(2-pyrazinyl)pyridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 3h; Negishi cross-coupling; Inert atmosphere; | 99% |
2-chloropyrazin
2-Methoxyphenylboronic acid
2-(2-methoxyphenyl)pyrazine
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
3-methoxyphenylboronic acid
2-(3-methoxyphenyl)-pyrazine
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
4-fluoro-2-methylphenylboronic acid
2-(4-fluoro-2-methylphenyl)pyrazine
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% |
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
potassium thioacyanate
Conditions | Yield |
---|---|
In water at 20℃; for 24h; | 98.6% |
2-chloropyrazin
nickel(II) thiocyanate
Conditions | Yield |
---|---|
at 20℃; for 72h; | 98.5% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 168h; | 98.3% |
2-chloropyrazin
potassium enolate of acetone
1-(pyrazin-2-yl)propan-2-one
Conditions | Yield |
---|---|
In diethyl ether; ammonia for 0.25h; Mechanism; Product distribution; effect of inhibitor (di-tert-butyl-nitroxide); | 98% |
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 36h; Heating; | 98% |
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% |
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% |
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
2-Methylphenylboronic acid
2-(2-methylphenyl)pyrazine
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% |
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; |
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% |
Conditions | Yield |
---|---|
In water at 20℃; for 48h; | 97.6% |
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
2,2'-bipyrazine
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% |
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 (CAS NO.14508-49-7) is used as intermediates of medicine and pesticide.
Hazard Codes: Xi
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 (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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