MONOBROMOBIMANE synthesis
- Product Name:MONOBROMOBIMANE
- CAS Number:71418-44-5
- Molecular formula:C10H11BrN2O2
- Molecular Weight:271.11
68654-22-8
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71418-44-5
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Yield:71418-44-5 50%
Reaction Conditions:
with N-Bromosuccinimide in acetonitrile at 0 - 20; for 12.5 h;
Steps:
Synthesis of Monobromobimane (5) by Bromination of syn-(Me,Me)bimane (3) Using NBS
syn-(Me,Me)bimane (3, 0.5 g, 2.6 mmol) was dissolved in 50 mLacetonitrile. The reaction mixture was cooled to 0 °C. RecrystallizedNBS (0.46 g, 2.6 mmol, CAS. 128-08-5) was slowly(pinchwise) added to the cooled reaction mixture over a periodof 30 min. After the addition of N-bromosuccinimide was complete,the reaction mixture was stirred at rt for 12 h. The solventwas then removed under reduced pressure. The residue waspurified using flash chromatography eluted with hexane/ethylacetate (1:1). The product 5 (0.35 g, 50% yield) was isolated. 1HNMR (CDCl3, 400 MHz): δ = 1.84 (s, 3 H), 1.89 (s, 3 H), 2.45 (s, 3H), 4.32 (s, 2 H) ppm. 13C NMR (CDCl3, 100 MHz): δ = 6.9, 11.5,17.8, 113.2, 115.4, 144.2, 146.0, 159.8, 160.7 ppm. ESI-MS: m/zcalcd for C10H12BrN2O2: 271.0082 [MH+]; found: 271.0067.
References:
Neogi, Ishita;Das, Partha J.;Grynszpan, Flavio [Synlett,2018,vol. 29,# 8,art. no. ST-2017-B0911-L,p. 1043 - 1046]
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6628-22-4
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71418-44-5
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68654-22-8
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$215.00/100mg
71418-44-5
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609-14-3
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71418-44-5
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