2-Amino-5-bromopyrazine supplier

Name
2-Amino-5-bromopyrazine
EINECS 626-202-4
CAS No. 59489-71-3
Density 1.844 g/cm³
Solubility
Melting Point 113-117 °C(lit.)
Formula C₄H₄BrN₃
Boiling Point 274.2 °C at 760 mmHg
Molecular Weight 174
Flash Point 119.7 °C
Transport Information
Appearance Brown Needles
Safety 26-37/39-45-36/37/39-22
Risk Codes 22-36/38-43-44-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 5-bromopyrazin-2-amine;5-bromo-pyrazin-2-ylamine;5-Bromo-2-aminopyrazine;
PSA 51.80000
LogP 1.40250

Synthetic route

: 24241-18-7
2-amino-3,5-dibromopyrazine

: 59489-71-3
5-amino-2-bromopyrazine

Conditions

Conditions	Yield
With trifuran-2-yl-phosphane; palladium diacetate; triethylamine Reagent/catalyst; Solvent; regioselective reaction;	97%

: 5049-61-6
2-Aminopyrazine

: 59489-71-3
5-amino-2-bromopyrazine

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h; Reagent/catalyst; Solvent;	89%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃;	88%
With N-Bromosuccinimide In dichloromethane at 0℃; for 3.5h;	81.5%

: 5049-61-6
2-Aminopyrazine

A: 59489-71-3
5-amino-2-bromopyrazine

B: 24241-18-7
2-amino-3,5-dibromopyrazine

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 100℃; for 0.0833333h; Solvent; Temperature; Microwave irradiation;	A 88% B 6%
With N-Bromosuccinimide In dichloromethane at 0 - 5℃; for 2h;	A 62% B 12%
With N-Bromosuccinimide In dichloromethane at 0℃; for 2h;	A 62% B 12%
With pyridine; bromine In chloroform for 3h; Ambient temperature; 1.2 equivalent of bromine and pyridine;	A 36% B 10%

: 24241-18-7
2-amino-3,5-dibromopyrazine

A: 5049-61-6
2-Aminopyrazine

B: 59489-71-3
5-amino-2-bromopyrazine

Conditions

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine In dimethyl sulfoxide regioselective reaction;	A 10% B 87%

: 5049-61-6
2-Aminopyrazine

A: 59489-71-3
5-amino-2-bromopyrazine

B: 21943-12-4
3-bromo-pyrazine-2-amine

Conditions

Conditions	Yield
With bromodioxane In 1,4-dioxane at 100℃; for 0.5h; Reagent/catalyst; Solvent;	A 48% B 6%

: 5049-61-6
2-Aminopyrazine

A: 59489-71-3
5-amino-2-bromopyrazine

B: 21943-12-4
3-bromo-pyrazine-2-amine

C: 24241-18-7
2-amino-3,5-dibromopyrazine

Conditions

Conditions	Yield
With pyridine; bromine In chloroform for 3h; Ambient temperature; 1.1 equivalent bromine and pyridine;	A 35% B 0.5% C 7%

...Expand

: 486424-37-7
3-amino-6-bromo-pyrazine-2-carboxylic acid

: 59489-71-3
5-amino-2-bromopyrazine

Conditions

Conditions	Yield
With tetralin

: 59489-71-3
5-amino-2-bromopyrazine

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 1245215-89-7
(E)-N’-(5-bromopyrazin-2-yl)-N,N-dimethylformamidine

Conditions

Conditions	Yield
at 60℃; for 2h;	100%
In isopropyl alcohol at 80℃; for 4h;	57%

: 59489-71-3
5-amino-2-bromopyrazine

: 3-methoxycyclobutane-1-carboxylic acid

: N-(5-bromopyrazin-2-yl)-3-methoxycyclobutanecarboxamide

Conditions

Conditions	Yield
Stage #1: 5-amino-2-bromopyrazine; 3-methoxycyclobutane-1-carboxylic acid With pyridine In acetonitrile at 20℃; for 0.0833333h; Stage #2: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate; acetonitrile at 20℃; for 12h;	100%

: 59489-71-3
5-amino-2-bromopyrazine

: 5006-22-4
Cyclobutanecarbonyl chloride

: N-(5-bromopyrazin-2-yl)cyclobutanecarboxamide

Conditions

Conditions	Yield
With pyridine at 0℃; for 0.25h;	100%

: 557-21-1
zinc(II) cyanide

: 59489-71-3
5-amino-2-bromopyrazine

: 113305-94-5
2-amino-5-cyanopyrazine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene at 100℃; for 2h;	100%

: 59489-71-3
5-amino-2-bromopyrazine

: 5720-07-0
4-methoxyphenylboronic acid

: 119738-50-0
2-amino-5-(4'-methoxyphenyl)-1,4-pyrazine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide Suzuki-Miyaura Coupling; Reflux;	99%
With bis(benzonitrile)palladium(II) dichloride; sodium carbonate; 1,4-di(diphenylphosphino)-butane In ethanol; toluene for 24h; Heating;	78%
With sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; methanol; water for 7h; Reflux;
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;

: 59489-71-3
5-amino-2-bromopyrazine

: 75-36-5
acetyl chloride

: 174680-67-2
N-(5-bromopyrazin-2-yl)acetamide

Conditions

Conditions	Yield
With pyridine In dichloromethane for 1h;	99%

: 59489-71-3
5-amino-2-bromopyrazine

: 98-80-6
phenylboronic acid

: 13535-13-2
2-amino-5-phenylpyrazine

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; isopropyl alcohol at 150℃; for 0.166667h; microwave reactor;	99%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene at 105℃; for 5h; Inert atmosphere;	92.8%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 12h; Suzuki Coupling; Inert atmosphere; Reflux; regioselective reaction;	74%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; N,N-dimethyl-formamide; toluene at 87℃; Reagent/catalyst; Solvent; Time; Inert atmosphere; Large scale;	1.82 kg
With bis(benzonitrile)palladium(II) dichloride; [1,4-bis(diphenylphosphino)butane] palladium(ll) dichloride; sodium carbonate In ethanol; water; toluene Reflux;

: 59489-71-3
5-amino-2-bromopyrazine

: 557-20-0
diethylzinc

: 13535-07-4
2-amino-5-ethylpyrazine

Conditions

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane; toluene at 12 - 21℃; for 4h; Inert atmosphere;	99%

: 59489-71-3
5-amino-2-bromopyrazine

: 4023-34-1
cyclopropanecarboxylic acid chloride

: N-(5-bromopyrazin-2-yl)cyclopropanecarboxamide

Conditions

Conditions	Yield
With pyridine at 0℃; for 15h;	99%

: 59489-71-3
5-amino-2-bromopyrazine

: 3282-30-2
pivaloyl chloride

: 710322-28-4
N-(5-bromo-pyrazin-2-yl)-2,2-dimethylpropionamide

Conditions

Conditions	Yield
With pyridine In ethanol; dichloromethane; water	98.21%
With pyridine In dichloromethane at 0 - 25℃; for 22.5h;	82%
With pyridine In dichloromethane at 0 - 25℃; for 22.5h;	82%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	82%

: 59489-71-3
5-amino-2-bromopyrazine

: 108-24-7
acetic anhydride

: 174680-67-2
N-(5-bromopyrazin-2-yl)acetamide

Conditions

Conditions	Yield
at 20℃; for 12h;	98%
Product distribution / selectivity;

: 59489-71-3
5-amino-2-bromopyrazine

: 126726-62-3
2-isopropenyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

: 5-isopropenylpyrazin-2-amine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 12h; Inert atmosphere;	97%

: 59489-71-3
5-amino-2-bromopyrazine

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 100-52-7
benzaldehyde

: 1021950-89-9
C16H17BrN4

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol at 20℃; for 2h;	96%

...Expand

: 59489-71-3
5-amino-2-bromopyrazine

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: tert-butyl 4-(4-(5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling; Inert atmosphere; Sealed tube;	96%

: 59489-71-3
5-amino-2-bromopyrazine

: 145240-28-4
4-butylphenylboronic acid

: C14H17N3

Conditions

Conditions	Yield
With potassium carbonate In water; toluene at 90℃; for 0.5h; Suzuki-Miyaura Coupling;	96%

: 59489-71-3
5-amino-2-bromopyrazine

: 133997-05-4
(4-octylphenyl)boronic acid

: 1353879-67-0
C18H25N3

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate In water; acetonitrile for 6h; Suzuki-Miyaura coupling; Reflux;	95%

: 59489-71-3
5-amino-2-bromopyrazine

: 5392-10-9
2-bromo-4,5-dimethoxybenzaldehyde

: 88333-03-3, 10340-91-7
Benzyl isocyanide

: 1402350-37-1
N-benzyl-6-bromo-2-(2-bromo-4,5-dimethoxyphenyl)imidazo[1,2-a]pyrazin-3-amine

Conditions

Conditions	Yield
With perchloric acid In methanol at 20℃;	95%

...Expand

: 59489-71-3
5-amino-2-bromopyrazine

: 151-50-8
potassium cyanide

: 113305-94-5
2-amino-5-cyanopyrazine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h; Heating / reflux;	94.4%
With copper(l) iodide; 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 2h; Heating;	88%
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In N,N-dimethyl-formamide at 200℃; for 1h;	36%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether In N,N-dimethyl-formamide at 20℃; Heating / reflux;

: potassium cyanide

: 59489-71-3
5-amino-2-bromopyrazine

: 113305-94-5
2-amino-5-cyanopyrazine

Conditions

Conditions	Yield
With copper(l) iodide; 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide) at 20℃; for 3.5h; Heating / reflux;	94.4%

: 59489-71-3
5-amino-2-bromopyrazine

: 143-33-9
sodium cyanide

: 544-92-3
copper(I) cyanide

: 113305-94-5
2-amino-5-cyanopyrazine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃;	93%
In N,N-dimethyl-formamide at 120℃;	93%
In N,N-dimethyl-formamide at 120℃;	93%

...Expand

: 59489-71-3
5-amino-2-bromopyrazine

: 25016-12-0
1,3-dimethyl-1H-pyrazole-4-carbaldehyde

: 945978-42-7
(5-bromo-pyrazin-2-yl)-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)amine

Conditions

Conditions	Yield
In acetic acid	93%
In acetic acid	93%
With trimethylamine-borane; acetic acid In methanol at 20℃;	93%

: 59489-71-3
5-amino-2-bromopyrazine

: 55552-70-0
furan-3-boronic acid

: 5-furan-3-yl-pyrazin-2-ylamine

Conditions

Conditions	Yield
With sodium carbonate; tetrakis (triphenylphosphine) palladium (0) In 1,2-dimethoxyethane; ethanol; water for 0.75h; Heating / reflux;	92.5%

: 59489-71-3
5-amino-2-bromopyrazine

: 2719-27-9
cyclohexanylcarbonyl chloride

: 940959-31-9
cyclohexanecarboxylic acid (5-bromo-pyrazin-2-yl)-amide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1h;	92%

: 59489-71-3
5-amino-2-bromopyrazine

: 137-26-8
Thiram

: 5-aminopyrazin-2-yl dimethylcarbamodithioate

Conditions

Conditions	Yield
With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 110℃; for 48h; Sealed tube;	92%

: 59489-71-3
5-amino-2-bromopyrazine

: 99768-12-4
4-methoxycarbonylphenylboronic acid

: 1021918-64-8
methyl 4-(5-aminopyrazin-2-yl)benzoate

Conditions

Conditions	Yield
Stage #1: 5-amino-2-bromopyrazine; 4-methoxycarbonylphenylboronic acid With potassium phosphate In 1,4-dioxane; water at 20℃; for 1h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 16h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	91%
Stage #1: 5-amino-2-bromopyrazine; 4-methoxycarbonylphenylboronic acid With potassium carbonate In 1,4-dioxane; water at 20℃; for 0.666667h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water for 4h; Suzuki Coupling; Reflux;	57%
With sodium carbonate; 1,1'-bis-(diphenylphosphino)ferrocene In 1,4-dioxane; water at 100℃; for 16h;	50%
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In 1,4-dioxane; water at 20℃; for 16h; Suzuki Coupling; Inert atmosphere; Reflux;
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;

: 59489-71-3
5-amino-2-bromopyrazine

: 76782-82-6
tert-Butyldimethyl(prop-2-ynyloxy)silane

: 1137476-16-4
2-amino-5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazine

Conditions

Conditions	Yield
With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 60℃;	91%

: 59489-71-3
5-amino-2-bromopyrazine

: 1152274-62-8
(2-methyl-4-(N-methylsulfamoyl)phenyl)boronic acid

: 1612287-91-8
4-(5-aminopyrazin-2-yl)-N,3-dimethylbenzenesulfonamide

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane at 100℃; for 3h; Schlenk technique; Inert atmosphere;	91%

: 59489-71-3
5-amino-2-bromopyrazine

: 24241-18-7
2-amino-3,5-dibromopyrazine

Conditions

Conditions	Yield
With N-Bromosuccinimide In chloroform at 0 - 20℃; for 6.5h; Solvent;	91%
With N-Bromosuccinimide In dichloromethane

: 59489-71-3
5-amino-2-bromopyrazine

: 159191-56-7
(4-((tert-butyldimethylsilyl)oxy)phenyl)boronic acid

: 549503-20-0
5-(p-tert-butyldimethylsilyloxyphenyl)-2-amino-1,4-pyrazine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; water; toluene for 17h; Inert atmosphere; Reflux;	90.2%
With sodium carbonate; PdCl2(PPh2(CH2)4PPh2) In toluene for 24h; Suzuki reaction; Heating;	72%
With sodium carbonate; 1,4-di(diphenylphosphino)-butane; palladium dichloride In ethanol; water; toluene for 15h; Suzuki coupling; Reflux; Inert atmosphere;
With sodium carbonate; dichlorobis(triphenylphosphine)palladium[II] In ethanol; water; toluene
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In ethanol; toluene at 80 - 150℃; Suzuki Coupling;

2-Amino-5-bromopyrazine Chemical Properties

Molecular Structure of 2-Amino-5-bromopyrazine (CAS NO.59489-71-3):

IUPAC Name: 5-bromopyrazin-2-amine
Empirical Formula: C₄H₄BrN₃
Molecular Weight: 173.9987
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 0
Polar Surface Area: 29.02 Å²
Index of Refraction: 1.648
Molar Refractivity: 34.36 cm³
Molar Volume: 94.3 cm³
Surface Tension: 68.9 dyne/cm
Density: 1.844 g/cm³
Flash Point: 119.7 °C
Enthalpy of Vaporization: 51.26 kJ/mol
Boiling Point: 274.2 °C at 760 mmHg
Vapour Pressure: 0.00547 mmHg at 25°C
Melting point: 113-117 °C(lit.)
Product Categories: Amines and Anilines; Heterocycles; pharmacetical; Halides; Pyrazines, Pyrimidines & Pyridazines; Pyrazine; Nucleotides and Nucleosides; Pyrazines; Chloropyrazines, etc.; Bases & Related Reagents; Nucleotides; Pyrazines, Pyrimidines & Pyridazines; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; PyrazinesHeterocyclic Building Blocks

2-Amino-5-bromopyrazine Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 22-36/38-43-44-36/37/38-20/21/22
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
R43:May cause sensitization by skin contact.
R44:Risk of explosion if heated under confinement.
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-37/39-45-36/37/39-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S22:Do not breathe dust.
WGK Germany: 3
Hazard Note: Irritant

2-Amino-5-bromopyrazine Specification

2-Amino-5-bromopyrazine , with CAS number of 59489-71-3, can be called 5-Bromopyrazinamine ; 5-Bromopyrazin-2-amine ; 5-Bromo-pyrazin-2-ylamine ; 5-Bromo-2-pyrazinamine ; 5-Bromo-2-aminopyrazine ; 5-Bromo-2-pyrazinamine, 97% . It is a brown needle.

Product Name

2-Amino-5-bromopyrazine

Synthetic route

2-Amino-5-bromopyrazine Chemical Properties

2-Amino-5-bromopyrazine Safety Profile

2-Amino-5-bromopyrazine Specification

Related Products

Hot Products