• Name

  2-Chloro-6-aminopyrazine

• EINECS 206-027-6
• CAS No. 33332-28-4
• Article Data17
• CAS DataBase
• Density 1.437 g/cm³
• Solubility
• Melting Point 150-152 °C
• Formula C₄H₄ClN₃
• Boiling Point 282.8 °C at 760 mmHg
• Molecular Weight 129.549
• Flash Point 124.8 °C
• Transport Information
• Appearance Colorless or off-white solid
• Safety 26-36/37/39
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi
• Synonyms 2-Pyrazinamine,6-chloro-;Pyrazinamine,6-chloro- (9CI);Pyrazine, 2-amino-6-chloro- (7CI,8CI);2-Amino-6-chloropyrazine;6-Amino-2-chloropyrazine;6-Chloro-2-aminopyrazine;6-Chloro-2-pyrazinamine;6-Chloro-2-pyrazinylamine;
• PSA 51.80000
• LogP 1.29340

Synthetic route

4774-14-5

2,6-dichloropyrazine

33332-28-4

2-amino-6-chloropyrazine

Conditions

Conditions	Yield
With ammonia at 100℃; for 5h; Temperature;	95%
With ammonia In water at 100℃; Inert atmosphere; sealed tube;	91%
With ammonia In water at 100℃; for 18h; Sealed tube;	91%

355836-31-6

6-chloro-N-(4-methoxybenzyl)pyrazin-2-amine

33332-28-4

2-amino-6-chloropyrazine

Conditions

Conditions	Yield
In trifluoroacetic acid	77%

6863-77-0

3-aminopyrazine 1-oxide

A

6863-73-6

3-chloropyrazin-2-amine

B

33332-29-5

2-amino-5-chloropyrazine

C

33332-28-4

2-amino-6-chloropyrazine

Conditions

Conditions	Yield
With trichlorophosphate for 2h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With trichlorophosphate for 2h; Product distribution; Mechanism; Heating; other substituted pyrazine-1-oxides and products, deoxygenation/chlorination competition; other time;

...Expand

33332-28-4

2-amino-6-chloropyrazine

98-80-6

phenylboronic acid

41270-69-3

2-amino-6-phenylpyrazine

Conditions

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; toluene at 100℃; Inert atmosphere;	100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 20 - 90℃; for 16.1667h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	83%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	83%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	83%
With potassium phosphate; 1,1'-bis(di-tertbutylphosphino)ferrocene; palladium diacetate In 1,4-dioxane at 100℃; for 5h; Suzuki coupling; Inert atmosphere; Sealed tube;	55%

1765-93-1

4-fluoroboronic acid

33332-28-4

2-amino-6-chloropyrazine

1159815-52-7

6-(4-fluoro-phenyl)-pyrazin-2ylamine

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 20℃; for 20h; Reflux;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	68%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	68%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 95℃; for 12h; Inert atmosphere;

3143-02-0

3-hydroxymethyl-3-methyloxethane

33332-28-4

2-amino-6-chloropyrazine

1431654-81-7

6-((3-methyloxetan-3-yl)methoxy)pyrazin-2-amine

Conditions

Conditions	Yield
Stage #1: 3-hydroxymethyl-3-methyloxethane With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 2h; Stage #2: 2-amino-6-chloropyrazine for 16h; Reflux;	100%
Stage #1: 3-hydroxymethyl-3-methyloxethane With sodium hydride In 1,4-dioxane; mineral oil at 20℃; for 2h; Stage #2: 2-amino-6-chloropyrazine In 1,4-dioxane; mineral oil for 16h; Reflux;	100%

24424-99-5

di-tert-butyl dicarbonate

33332-28-4

2-amino-6-chloropyrazine

815610-07-2

N-(tert-butoxycarbonyl)-N-(6-chloropyrazin-2-yl) tert-butylcarbamate

Conditions

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 2h;	98%
With dmap In dichloromethane at 20℃; for 3h;	98%
With dmap In tetrahydrofuran at 20℃; for 8h;	88.4%

33332-28-4

2-amino-6-chloropyrazine

960510-36-5

2-amino-5-bromo-3,6-dichloropyrazine

Conditions

Conditions	Yield
Stage #1: 2-amino-6-chloropyrazine With N-Bromosuccinimide In methanol at 50℃; for 19h; Stage #2: With N-chloro-succinimide In methanol at 38 - 50℃; for 16h;	97%
Stage #1: 2-amino-6-chloropyrazine With N-Bromosuccinimide In methanol at 50℃; for 19h; Stage #2: With N-chloro-succinimide In methanol at 38 - 50℃; for 16h;	97%
Stage #1: 2-amino-6-chloropyrazine With N-Bromosuccinimide In methanol at 50℃; for 19h; Stage #2: With N-chloro-succinimide In methanol at 38 - 50℃; for 16h;	97%
Stage #1: 2-amino-6-chloropyrazine With N-Bromosuccinimide In methanol at 50℃; for 19h; Stage #2: With N-chloro-succinimide at 50℃; for 16h;	97%
Stage #1: 2-amino-6-chloropyrazine With N-Bromosuccinimide In methanol for 17h; Stage #2: With N-chloro-succinimide; N-Bromosuccinimide In methanol at 38 - 50℃; for 18h;	97%

33332-28-4

2-amino-6-chloropyrazine

1711-06-4

3-Methylbenzoyl chloride

1194688-06-6

N-(6-chloropyrazin-2-yl)-3-methylbenzamide

Conditions

Conditions	Yield
With pyridine at 100℃; for 16h;	97%

33332-28-4

2-amino-6-chloropyrazine

925678-00-8

6-chloro-5-iodo-pyrazin-2-ylamine

Conditions

Conditions	Yield
With N-iodo-succinimide In dimethyl sulfoxide at 25℃;	88%
With N-iodo-succinimide In dimethyl sulfoxide at 20℃; for 72h;	80%
With N-iodo-succinimide In dimethyl sulfoxide at 20℃; for 72h;	80%

77287-34-4, 77287-35-5, 60100-09-6

formamide

33332-28-4

2-amino-6-chloropyrazine

1125-84-4

7-chloropteridine

Conditions

Conditions	Yield
With phosphorus tribromide at 50 - 60℃; Inert atmosphere;	87%

2162-31-4

2-(tetrahydropyran-2-yloxy)ethanol

33332-28-4

2-amino-6-chloropyrazine

6-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)pyrazin-2-amine

Conditions

Conditions	Yield
Stage #1: 2-(tetrahydropyran-2-yloxy)ethanol With sodium hydride In 1,4-dioxane at 0 - 20℃; for 0.5h; Stage #2: 2-amino-6-chloropyrazine In 1,4-dioxane at 0 - 80℃; for 16h;	87%

1692-25-7

3-pyridylboronic acid

33332-28-4

2-amino-6-chloropyrazine

925677-98-1

6-pyridin-3-ylpyrazin-2-amine

Conditions

Conditions	Yield
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling;	86%

68-12-2, 33513-42-7

N,N-dimethyl-formamide

33332-28-4

2-amino-6-chloropyrazine

N'-(6-chloropyrazin-2-yl)-N,N-dimethylformamidine hydrochloride

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With phenyl chloroformate at 20℃; for 0.0833333h; Stage #2: 2-amino-6-chloropyrazine for 0.0833333h; Mechanism; Reagent/catalyst; Concentration;	86%

617-84-5

N-formyldiethylamine

33332-28-4

2-amino-6-chloropyrazine

1448017-68-2

N'-(6-chloropyrazin-2-yl)-N,N-diethylformamidine

Conditions

Conditions	Yield
Stage #1: N-formyldiethylamine With phenyl chloroformate at 20℃; for 0.166667h; Stage #2: 2-amino-6-chloropyrazine at 45℃; for 0.0833333h; Stage #3: With potassium carbonate	85%

89787-12-2

2-isopropylphenylboronic acid

33332-28-4

2-amino-6-chloropyrazine

6-(2-isopropylphenyl)pyrazin-2-amine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 120℃; for 3h; Microwave irradiation;	84.6%

1421822-66-3

(S)-2-(2-methylpyrrolidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

33332-28-4

2-amino-6-chloropyrazine

1620136-71-1

(S)-6-(2-(2-methylpyrrolidin-1-yl)pyrimidin-5-yl)pyrazin-2-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 25 - 90℃; Inert atmosphere;	84%

108-16-7

1-methyl-2-N,N-dimethylaminoethanol

33332-28-4

2-amino-6-chloropyrazine

936004-96-5

6-[1-(dimethylamino)propan-2-yloxy]pyrazin-2-amine

Conditions

Conditions	Yield
Stage #1: 1-methyl-2-N,N-dimethylaminoethanol With sodium hydride In 1,4-dioxane for 0.5h; Stage #2: 2-amino-6-chloropyrazine In 1,4-dioxane at 100℃; Further stages.;	83%

(2-(3-azabicyclo[3.1.0]hexan-3-yl)pyrimidin-5-yl)boronic acid

33332-28-4

2-amino-6-chloropyrazine

6-(2-(3-azabicyclo[3.1.0]hexan-3-yl)pyrimidin-5-yl)pyrazin-2-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 2h; Reagent/catalyst; Temperature; Inert atmosphere;	81.51%

33332-28-4

2-amino-6-chloropyrazine

1-(piperidin-1-yl)methanimine

1448017-69-3

6-chloro-N-(piperidin-1-ylmethylene)pyrazin-2-amine

Conditions

Conditions	Yield
Stage #1: 1-(piperidin-1-yl)methanimine With phenyl chloroformate at 20℃; for 0.0833333h; Stage #2: 2-amino-6-chloropyrazine at 45℃; for 0.0833333h; Stage #3: With potassium carbonate	81%

33332-28-4

2-amino-6-chloropyrazine

6905-47-1

6-Methoxy-pyrazin-2-ylamine

Conditions

Conditions	Yield
With sodium methylate In methanol	80%
In 1,4-dioxane; methanol; ethyl acetate	11%

67-56-1

methanol

3375-31-3

palladium diacetate

33332-28-4

2-amino-6-chloropyrazine

118853-60-4

methyl 6-amino-2-pyrazinecarboxylate

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; triethylamine at 85℃; under 7600.51 Torr; for 5h; Large scale;	80%

...Expand

13331-23-2

fur-2-ylboronic acid

33332-28-4

2-amino-6-chloropyrazine

925677-91-4

6-(furan-2-yl)pyrazin-2-amine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 18h; Inert atmosphere;	80%

1679-18-1

4-Chlorophenylboronic acid

33332-28-4

2-amino-6-chloropyrazine

C10H8ClN3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 100℃; for 18h; Inert atmosphere;	80%

2-Chloro-6-aminopyrazine Chemical Properties

2-Chloro-6-aminopyrazine Safety Profile

2-Chloro-6-aminopyrazine Specification