6327-97-5

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 23, p. 491, 1958 DOI: 10.1021/jo01097a610

InChI:InChI=1/C5H5BrN2O2/c1-8-2-3(6)4(9)7-5(8)10/h2H,1H3,(H,7,9,10)

Upstream product

• 615-77-0 1-methyluracil 
• 512-56-1 trimethyl phosphite 
• 51-20-7 5-bromouracil 
• 74-88-4 methyl iodide 
• 119255-08-2 5-acetoxymercuri-1-methyluracil 

Downstream Products

• 1373921-17-5 C₂₀H₂₇BrN₂O₄S 

Relevant academic research and scientific papers

Adenosine-1,3-diazaphenoxazine derivative for selective base pair formation with 8-oxo-2′-deoxyguanosine in DNA

The selective detection of 8-oxo-2′-deoxyguanosine (8-oxo-dG) in DNA without chemical or enzymatic treatment is an attractive tool for genomic research. We designed and synthesized the non-natural nucleoside analogue, the adenosine-1,3-diazaphenoxazine (A

Structural changes of an abasic site in duplex DNA affect noncovalent binding of the spin label C

The influence of structural changes of an abasic site in duplex DNA on noncovalent and site-directed spin labeling (NC-SDSL) of the spin label C were examined with electron paramagnetic resonance (EPR) spectroscopy. The binding affinities of C to sixteen

Halo-demercuration Reactions of the 1,3-Dimethyluracil and 1-Methyluracil 5-Substituted Mercurials

Detailed procedures are submitted for direct mercuration (with Hg(II) acetate or chloride) of 1,3-dimethyluracil (I) or 1-methyluracil (VIII) with formation, subsequently, of 5-acetoxymercuri-1,3-dimethyluracil (II), 5-chloromercuri-1,3-dimethyluracil (III) or 5-acetoxymercuri-1-methyluracil (IX) in 52percent, 64percent or 49percent yields, respectively; II with hot solution of NaCl gave III in 45percent yield, whereas from II in hot aq.KI solution 5,5'-mercuribis(1,3-dimethyluracil) (IV) was formed in 89percent yield.The mercurials II, IV or IX were effectively halo-demercurated forming thus: 5-iodo- (V), 5-bromo- (VI) and 5-chloro-1,3-dimethyluracil (VII) or (from IX) 5-bromo-1-methyluracil (X) in the respective yields: 83-88percent, 82-85percent, 74 or 78percent.The structures of I-X are supported chemically, in part analytically as well as by the 1H-NMR spectra (see the Figure).

The bromination and iodination of N1-substituted uracils

Reaction of N1-substituted uracils with bromine in water at pH=7 leads to 5-bromo-6-hydroxy-5,6-hydrouracils.For different N1-substituents these products were isolated and the relatively stable derivatives were characterized by 1H NMR and mass spectroscopy.On electrophilic iodination with iodide and chloramine-T in water no indications were obtained for the formation of such dihydrouracils except for uridine and deoxyuridine.However, on reaction of N1-substituted uracils with N-iodosuccinimide in CHCl3 containing ethanol, or in ethanol, 5-iodo-6-ethoxy-5,6-dihydrouracils could be isolated as reaction products.

Mechanisms of Bromination of Uracil Derivatives. 5. Reaction of Uracil and 5-Bromouracil via Their Anions in Weakly Acidic Aqueous Solution

The rates of reaction of bromine with uracil, 1-methyluracil, 3-methyluracil, 1,3-dimethyluracil, 5-bromouracil, and 5-bromo-1,3-dimethyluracil have been measured in acidic, aqueous solutions (pH 0-5).For those derivatives having a methyl group at N1 the observed second-order rate constants are invariant with acidity, whereas for those derivatives having hydrogen at N1 they increase with decreasing acidity.These results suggest that reaction upon the anions of uracil, 3-methyluracil, and 5-bromouracil predominates at higher pH.The mechanistic implications of these findings are discussed.