| Identification | More | [Name]
2-Amino-3,5-dibromopyrazine | [CAS]
24241-18-7 | [Synonyms]
2-AMINO-3,5-DIBROMOPYRAZINE
3,5-DIBROMOPYRAZIN-2-AMINE
3,5-DIBROMOPYRAZIN-2-YLAMINE
3,5-DIBROMOPYRAZINE-2-YLAMINE
2-AMINO-3,5-DIBROMOPYRAZIN
3,5-dibromo-2-Pyrazinamine | [Molecular Formula]
C4H3Br2N3 | [MDL Number]
MFCD00673150 | [Molecular Weight]
252.89 | [MOL File]
24241-18-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
114-117 °C (lit.) | [Boiling point ]
294.6±35.0 °C(Predicted) | [density ]
2.287±0.06 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
0.81±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/39:Wear suitable protective clothing and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [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. | [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 |
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