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| | 2-Amino-3,5-dibromopyrazine Basic information |
| Product Name: | 2-Amino-3,5-dibromopyrazine | | Synonyms: | 2-AMINO-3,5-DIBROMOPYRAZINE;3,5-DIBROMOPYRAZIN-2-YLAMINE;3,5-DIBROMOPYRAZINE-2-YLAMINE;3,5-DIBROMOPYRAZIN-2-AMINE;2-AMINO-3,5-DIBROMOPYRAZIN;3,5-dibromo-2-Pyrazinamine;3,5-dibromo-2-aminopyrazine;2-Amino-3,5-dibromopyrazine ,98% | | CAS: | 24241-18-7 | | MF: | C4H3Br2N3 | | MW: | 252.89 | | EINECS: | | | Product Categories: | Chloropyrazines, etc.;Pyrazine;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PyrazinesHeterocyclic Building Blocks;Pyrazines;pharmacetical;amine| alkyl bromide | | Mol File: | 24241-18-7.mol |  |
| | 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 | | 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) |
| 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 | | Storage Class | 6.1D - Non-combustible acute toxic Cat.3
toxic hazardous materials or hazardous materials causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| | 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 Preparation Products And Raw materials |
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