2-iodopyrazine
2-Aminopyrazine
Conditions | Yield |
---|---|
With copper(I) oxide; ammonia; potassium carbonate In 1,4-dioxane at 140℃; under 7757.43 Torr; for 16h; | 92% |
With copper(I) oxide; ammonium hydroxide; potassium carbonate at 140℃; for 16h; Inert atmosphere; | 49% |
2-amino-3,5-dibromopyrazine
A
2-Aminopyrazine
B
5-amino-2-bromopyrazine
Conditions | Yield |
---|---|
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In dimethyl sulfoxide regioselective reaction; | A 10% B 87% |
2-pyrazine carbonitrile
2-Aminopyrazine
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hydroxide at 20 - 60℃; for 5h; | 82.6% |
With sodium hypochlorite; potassium hydroxide; sodium hydroxide at 40℃; for 2h; pH=8; Temperature; | |
With sodium hypochlorite; water; sodium hydroxide at -5 - 100℃; | 74 g |
Conditions | Yield |
---|---|
With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; Schlenk technique; | A 79% B n/a |
2-chloropyrazin
2-Aminopyrazine
Conditions | Yield |
---|---|
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; | 75% |
With ammonia; water at 200℃; | |
With ammonia In dimethyl sulfoxide at 130℃; |
phthalimide
A
2-Aminopyrazine
B
2-(5-Amino-pyrazin-2-ylmethyl)-isoindole-1,3-dione
Conditions | Yield |
---|---|
With sodium carbonate In CH2Cl2/MeOH; dichloromethane; trifluoroacetic acid | A n/a B 73% |
Conditions | Yield |
---|---|
With potassium permanganate; potassium amide In ammonia for 0.166667h; | 65% |
Conditions | Yield |
---|---|
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction; | 52% |
2-(1-hydroxyethyl)pyrazine
2-Aminopyrazine
Conditions | Yield |
---|---|
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 12h; | 45% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction; | A n/a B 28% |
N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
A
2-Aminopyrazine
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; potassium carbonate In acetonitrile; benzene at 80℃; for 24h; | A 20% B 24% |
N-(3',5'-dibromopyrazin-2'-yl)pyridinium aminide
benzene
A
2-Aminopyrazine
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; potassium carbonate In acetonitrile at 80℃; for 24h; | A 20% B 24% C 20% |
Conditions | Yield |
---|---|
With sodium hypochlorite Behandeln des erhaltenen Natrium-Salzes der Pyrazinylcarbamidsaeure C5H5N3O2(Kristalle;Verfaerbung ab 257grad)mit wss.Saeuren.; |
Conditions | Yield |
---|---|
With diethylene glycol monoethyl ether acetate at 210 - 245℃; | |
With nitrobenzene | |
Erhitzen ueber den Schmelzpunkt; |
Conditions | Yield |
---|---|
With sulfuric acid at 240 - 245℃; |
Conditions | Yield |
---|---|
With sodium hydroxide; trichlorophosphate 1) 70 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
N-(Tetrazolyl-5')-2-pyrazinylamine
A
2-Aminopyrazine
B
[1,2,4] triazolo[1,5-a]pyrazin-2-amine
Conditions | Yield |
---|---|
With PPA at 290℃; |
9-tert-butylfluorene
A
2-Aminopyrazine
B
potassium salt of 9-tert-butylfluorene
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 24.9℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With polystyrene Wang resin; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid 1.) toluene, 100 deg C, 16 h, 2.) CH2Cl2, 5 min; Yield given; Multistep reaction; |
Conditions | Yield |
---|---|
at 240 - 245℃; |
2-Aminopyrazine
Conditions | Yield |
---|---|
beim Erhitzen ueber den Schmelzpunkt; |
Conditions | Yield |
---|---|
at 70℃; | 100% |
With sodium hydrogencarbonate at 100℃; for 48h; Inert atmosphere; | 50% |
With sodium hydrogencarbonate at 100℃; for 48h; | 50% |
2-Aminopyrazine
phenylglyoxal hydrate
2-phenylimidazo<1,2-a>pyrazin-3(7H)-one
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 168h; | 100% |
With hydrogenchloride In ethanol at 20 - 25℃; for 18h; | 49% |
With hydrogenchloride In ethanol; water at 20℃; for 15h; Cyclization; | 20% |
2-Aminopyrazine
4-chlorophenylglyoxal
2-(4-Chloro-phenyl)-7H-imidazo[1,2-a]pyrazin-3-one
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane for 264h; | 100% |
Conditions | Yield |
---|---|
In toluene for 2.25h; Heating / reflux; | 100% |
2-Aminopyrazine
methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate
(2S,4R)-1-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-6-morpholino-1,3,5-triazin-2-yl)-4-fluoro-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide
Conditions | Yield |
---|---|
Stage #1: 2-Aminopyrazine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; Stage #2: methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate In tetrahydrofuran at 20℃; for 4h; | 100% |
Conditions | Yield |
---|---|
In ethanol at 25℃; | 100% |
2-Aminopyrazine
2-aminopyrazine 1-oxide
Conditions | Yield |
---|---|
With hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid In methanol; N,N-dimethyl-formamide at 25℃; for 1h; | 99% |
With 3-chloro-benzenecarboperoxoic acid In acetone for 24h; Ambient temperature; | 63% |
Conditions | Yield |
---|---|
With lanthanum chloride heptahydrate In neat (no solvent) at 60℃; for 0.416667h; Green chemistry; | 99% |
In neat (no solvent) at 20℃; for 2.5h; Sealed tube; Irradiation; Green chemistry; | 96% |
In neat (no solvent) at 160℃; for 1.5h; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With sodium phenoxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 80℃; for 2h; | 99% |
2-Aminopyrazine
Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2
[Cu2(1,1'-(1,3-phenylene)-bis(4,4-dimethylpentane-1,3-dione(2-))2(aminopyrazine)]2
Conditions | Yield |
---|---|
In tetrahydrofuran stirred soln. of Cu-complex and ligand in THF brought to boiling, cooled; Et2O slow diffused; elem. anal.; | 99% |
Conditions | Yield |
---|---|
With pyridine at 0℃; for 2h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(π-crotyl)Pd(BrettPhos)]OTf; potassium carbonate In tert-Amyl alcohol at 110℃; for 2h; Schlenk technique; Inert atmosphere; | 99% |
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; [(π-crotyl)Pd(BrettPhos)]OTf; potassium carbonate In tert-Amyl alcohol at 110℃; for 2h; Schlenk technique; Inert atmosphere; | 99% |
2-Aminopyrazine
2-amino-3,5-dibromopyrazine
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 100℃; for 0.0833333h; Solvent; Microwave irradiation; | 98% |
With 2,6-dimethylpyridine; bromine In dichloromethane | 95% |
With bromine; sodium hydrogencarbonate In acetic acid 1.) 2h, 2.) 1h; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 20h; | 98% |
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 100℃; for 24h; | 74% |
2-Aminopyrazine
4-methyl-benzaldehyde
β-naphthol
1-[p-methylphenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
Conditions | Yield |
---|---|
In water at 20℃; for 0.666667h; | 98% |
at 125℃; for 0.0666667h; Mannich reaction; Neat (no solvent); | 89% |
2-Aminopyrazine
4-chlorobenzaldehyde
β-naphthol
1-[p-chlorophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
Conditions | Yield |
---|---|
In water at 20℃; for 0.666667h; | 98% |
at 125℃; for 0.0666667h; Mannich reaction; Neat (no solvent); | 90% |
2-Aminopyrazine
4-bromo-benzaldehyde
β-naphthol
1-[p-bromophenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
Conditions | Yield |
---|---|
In water at 20℃; for 0.416667h; | 98% |
at 125℃; for 0.1h; Mannich reaction; Neat (no solvent); | 93% |
2-Aminopyrazine
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
at 120℃; for 6h; Autoclave; | 98% |
2-Aminopyrazine
ethyl trifluoroacetate,
2,2,2-trifluoro-N-(pyrazin-2-yl)acetamide
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran for 48h; Reflux; | 97.8% |
2-Aminopyrazine
triphenylphosphine
1,1,1-triphenyl-N-(pyrazin-2-yl)-λ5-phosphanimine
Conditions | Yield |
---|---|
With diethylazodicarboxylate In dichloromethane; toluene at 20℃; for 2.16667h; Mitsunobu type reaction; | 97% |
With hexachloroethane; triethylamine In acetonitrile 12 h, RT, then, reflux, 6 h; | 64% |
With hexachloroethane; triethylamine In benzene for 3h; Heating; | 64% |
2-Aminopyrazine
2,3-dibromopyridine
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium (0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 140℃; for 24h; | A n/a B 97% |
2-Aminopyrazine
benzaldehyde
β-naphthol
1-[phenyl(2-pyrazinylamino)methyl]naphthalene-2-ol
Conditions | Yield |
---|---|
In water at 20℃; for 0.583333h; | 97% |
at 125℃; for 0.05h; Mannich reaction; Neat (no solvent); | 94% |
cis,trans-2,5-dimethoxytetrahydrofuran
2-Aminopyrazine
(pyrrolyl-1)-2 pyrazine
Conditions | Yield |
---|---|
In water at 150℃; for 0.5h; Paal-Knorr condensation; Microwave irradiation; | 97% |
5-Methylfurfural
2-Aminopyrazine
Cyclohexyl isocyanide
N-cyclohexyl-2-(5-methylfuran-2-yl)imidazo[1,2-a]pyrazin-3-amine
Conditions | Yield |
---|---|
Stage #1: 5-Methylfurfural; 2-Aminopyrazine With scandium tris(trifluoromethanesulfonate) In methanol at 20℃; for 1h; Ugi reaction; Stage #2: Cyclohexyl isocyanide In methanol Ugi reaction; | 97% |
Conditions | Yield |
---|---|
With C19H37IrN4(2+)*2I(1-); potassium carbonate at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; | 97% |
With [Cp*Ir(2-(1H-benzo[d]imidazol-2-yl)-1H-benzo[d]imidazole)Cl][Cl]; caesium carbonate at 120℃; for 12h; Schlenk technique; | 95% |
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydroxide at 150℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry; | 90% |
Conditions | Yield |
---|---|
With cerium(III) chloride heptahydrate In acetonitrile at 60℃; | 97% |
2-Aminopyrazine
tert-butylisonitrile
2-ethynylbenzaldehyde
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 20℃; for 12h; Inert atmosphere; | 96% |
2-Aminopyrazine
orthoformic acid triethyl ester
phosphonic acid diethyl ester
tetraethyl [(pyrazin-2-ylamino)methylene]bis(phosphonate)
Conditions | Yield |
---|---|
With copper(II) oxide In neat (no solvent) at 60℃; Microwave irradiation; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With SingaCycle-A1; potassium hexamethylsilazane In toluene at 100℃; for 24h; Schlenk technique; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
at 25℃; for 2h; | 96% |
IUPAC Name: Pyrazin-2-amine
Synonyms of 2-Aminopyrazine (CAS NO.5049-61-6): Aminopyrazine ; Pyrazinamine
CAS NO: 5049-61-6
Molecular Formula: C4H5N3
Molecular Weight: 95.10
Molecular Structure:
EINECS:225-748-7
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 0
Polar Surface Area: 29.02 Å2
Index of Refraction: 1.598
Molar Refractivity: 26.67 cm3
Molar Volume: 78.1 cm3
Surface Tension: 64.3 dyne/cm
Density: 1.216 g/cm3
Flash Point: 129.1 °C
Enthalpy of Vaporization: 48.82 kJ/mol
Boiling Point: 250.9 °C at 760 mmHg
Vapour Pressure: 0.0211 mmHg at 25°C
Melting Point: 118-120 °C(lit.)
Storage temp: Flammables area
Water Solubility: soluble
Appearance: slightly yellow to beige crystalline powder
Product Categories of 2-Aminopyrazine (CAS NO.5049-61-6): Fluorobenzene;pharmacetical;Pyrazine;API intermediates;Pyrazines;Chloropyrazines, etc.
Safety Information about 2-Aminopyrazine (CAS NO.5049-61-6):
Hazard Codes: XiF
Risk Statements: 36/37/38-11
R11: Highly flammable.
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.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
HS Code: 29339990
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Flammable solid.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Flammables-area.
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