3,5-Dibromo-2(1H)-pyrazinone
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3,5-Dibromo-2(1H)-pyrazinone
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CAS No:
21943-15-7
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Formula:
C4H2Br2N2O
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Chemical Name:
3,5-Dibromo-2(1H)-pyrazinone
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Synonyms:
2(1H)-Pyrazinone,3,5-dibromo-;Pyrazinol,3,5-dibromo-;3,5-Dibromo-2(1H)-pyrazinone;3,5-Dibromopyrazin-2-ol;3,5-Dibromo-1H-pyrazin-2-one;3,5-Dibromo-2-hydroxypyrazine;3,5-Dibromo-1,2-dihydropyrazin-2-one
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CAS No:
Safety Information
NONH for all modes of transport
1
22-41
26-39
Xn
P280-P305 + P351 + P338
H302-H318
|Danger|H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501|Aggregated GHS information provided by 40 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
3,5-Dibromo-2(1H)-pyrazinone Use and Manufacturing
Preparation of compound 36a: 3, 5-dibromopyrazin-2-olTo a stirred solution of 3, 5-dibromopyrazin-2-amine (30 g, 0.12 mol) in AcOH (300 ml_) was added dropwise cone. HGeneral procedure: The suspension of 18b (2.51 g, 10.0 mmol), NaCN (0.59 g, 12.0 mmol), CuI (0.95 g, 5.0 mmol) and Pd(PPh3)4 (0.14 g, 0.1 mmol) were stirred in DMF (20 mL) at 120 C for 10 h under nitrogen protection. After cooling to room temperature, 10% aqueous solution of Na2S2O3(10 mL) and water(50 mL) were added. The mixture was extracted with ethyl acetate (50 mL × 3), washed with water (3 × 50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography on silica gel eluting with PE/EA (10:1-2:1) to give an off-white solid (1.1 g, yield 55%).Preparation of compound 36a: 18b (3.0 g, 12 mmol) was added into acetic acid (20 mL) and concentrated sulfuric acid (4 mL) under ice bath. To this mixture was added a pre-prepared solution of NaNO2 (1.65 g, 24 mmol) in water (10 mL). The reaction mixturewas stirred at room temperature for 3 h, and then poured into ice water (100 g). The precipitate was collected by filtrated, washed with water and dried to give an off-white solid (1.8 g, yield 61%). 3, 5-Dibromo-2-hydroxylpyrazine (21b)Yield: 61%, off-white solid, M.p.: 182-184 C. 1H NMR(400 MHz, CDCl3):delta 11.23 (br, 1H), 7.53 (s, 1H). 1HNMR (400 MHz, DMSO-d6): delta 13.16 (s, 1H), 7.94 (s, 1H).13C NMR (125 MHz, CD3OD): delta 154.19, 136.73, 131.57, 114.62. ESI-MS m/z: 250.9 [M - H]-.Preparation of compound 36b: 3, 5-dibromo-2-methoxypyrazine To a stirred solution of 36a (8 g, 0.031 mol) in dry THF (100 mL) was added dropwise a solution of CH2N2 in Et2O (0.7 N, 134 mL, 0.093 mol) at 0 0C. After the addition, the resulting mixture was stirred at r.t. for 0.3 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (petroleum ether/EtOAc 10:1 ) which gave the title compound 36b as a yellow solid (5.5 g, 32.6%). 1H NMR (400 MHz, CDCI3) 3.963 (s, 3H), 8.060 (s, 1 H).
Computed Properties
Molecular Weight:253.88
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:253.85134
Monoisotopic Mass:251.85339
Topological Polar Surface Area:41.5
Heavy Atom Count:9
Complexity:209
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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