2-Amino-3,5-dibromopyrazine Chemical Properties

Melting point:

114-117 °C (lit.)

Boiling point:

294.6±35.0 °C(Predicted)

Density 

2.287±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Methanol

pka

0.81±0.10(Predicted)

form 

Powder

color 

Yellow to brown

InChI

InChI=1S/C4H3Br2N3/c5-2-1-8-4(7)3(6)9-2/h1H,(H2,7,8)

InChIKey

DTLBKXRFWUERQN-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Br)N=C1Br

CAS DataBase Reference

24241-18-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41

Safety Statements 

26-36/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

2-Amino-3,5-dibromopyrazine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

2-Amino-3,5-dibromopyrazine is used in the preparation of conjugated polymers for neurotoxin detection. 2-Amino-3,5-dibromopyrazine is an intermediate in the preparation of rho kinase (ROCK) inhibitor s.

Uses

2-Amino-3,5-dibromopyrazine may be used in the synthesis of:

• 2-amino-5-bromopyrazin-3-thiol
• 2-amino-3,5-bis(p-methoxyphenyl)-1,4-pyrazine
• 3,7-dihydroimidazo[1,2a]pyrazine-3-ones

General Description

2-Amino-3,5-dibromopyrazine can be synthesized from 2-aminopyrazine via bromination using N-bromosuccinimide (NBS). It reacts with sodium dicyanocuprate to form a mixture of mono and dicyanation products. The formation of 2-aminothiazolopyrazines by reacting 2-amino-3,5-dibromopyrazine with isothiocyanates has been reported.

Synthesis

The general procedure for the synthesis of 2-amino-3,5-dibromopyrazine from 2-aminopyrazine was as follows: 2-aminopyrazine (9.5 g, 100 mmol) was added to a reaction flask containing glacial acetic acid (70 mL) and heated on a steam bath until completely dissolved. Subsequently, sodium acetate trihydrate (33 g, 243 mmol) was added and constant stirring was maintained. The reaction mixture was cooled in an ice-salt bath at -5°C and bromine (16 mL) was added slowly and dropwise over a period of 4 hours (note: rapid addition of bromine may result in uncontrolled reaction and pose a safety hazard). After the dropwise addition was completed, stirring was continued in the ice bath for 2 hours, then moved to room temperature and stirred for 24 hours. Upon completion of the reaction, the mixture was poured into ice (50 g) and neutralized by adjusting to pH 8 with concentrated ammonia. The crude product was collected by filtration and recrystallized from methanol (with the addition of Norit activated charcoal) to give the final 2-amino-3,5-dibromopyrazine in colorless needles (16.8 g, 66% yield) with a melting point of 113-114 °C (literature value: 114-115 °C).

References

[1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986
[2] Journal of Organic Chemistry, 1983, vol. 48, # 7, p. 1064 - 1069
[3] RSC Advances, 2015, vol. 5, # 47, p. 37887 - 37895
[4] RSC Advances, 2018, vol. 8, # 18, p. 9707 - 9717
[5] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1149 - 1154

2-Amino-3,5-dibromopyrazine(24241-18-7)Related Product Information

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• Aminopyrazine
• 3-Aminophenol
• Glipizide
• Sulfachoropyrazine sodium
• ALTRENOGEST
• 3,5-DIBROMO-6-CHLOROPYRAZIN-2-AMINE
• Pyrazine
• 3,5-DIBROMO-N,N-DIMETHYLPYRAZINAMINE
• 2-AMINO-3,5-DIBROMO-6-METHYLPYRAZINE
• 2-Amino-3,5-dibromopyrazine
• AMINO ACIDS
• 3,5-DIBROMO-6-[4-(TRIFLUOROMETHYL)PHENYL]PYRAZIN-2-AMINE
• 3,5-DIBROMO-6-(4-FLUOROPHENYL)-N-METHYLPYRAZIN-2-AMINE