7V-bromosuccinimide

Bromomethylanthraquinone [7598-10-9] M 301.1, m 200-202°. Recrystd from AcOH, the crystals are washed with a little Et20, dried in air and then in vac at 100°. It is prepared by bromination of 2-methylanthraquinone with Br2/PhN02 at 145-150°, or 7V-bromosuccinimide in CCI4 containing a trace of (PhCOO)2. 

V-Bromosuccinimide [128-08-5] M 178.0, m 183-184°(dec). TV-Bromosuccinimide (30g) was dissolved rapidly in 3(X)mL of boiling water and filtered through a fluted filter paper into a flask immersed in an ice bath, and left for 2h. The crystals were filtered, washed thoroughly with ca l(X)mL of ice-cold water and drained on a Buchner funnel before drying under vac over P2O5 or CaCl2 [Dauben and McCoy J Am Chem Soc 81 4863 7959]. Has also been crystd from acetic acid or water (10 parts, washed in water and dried in vacuo, [Wilcox et al. J Am Chem Soc 108 7693 1986 Shell et al. J Am Chem Soc 108 121 7956 Phillips and Cohen J Am Chem Soc 108 2013 7956.]... 

Phenyl- and 2-methyl-6-phenyldihydrodiazepinium salts are haloge-nated at the p-position of the phenyl groups by N-bromo- and N-iodosuc-cinimide but not by A/-chlorosuccinimide, whereas the 1,4-dimethyI-6-phenyl derivative reacts only with the 7V-bromosuccinimide [81JCS-(PD726]. 

Symmetrically substituted 1,2,4-selenadiazoles (123) are obtained by oxidation of primary selenoamides with 7V-bromosuccinimide <91BCJ1037>. 

Satake et al. have described the mechanistic aspects of the formation of 2-methoxy-277-azepine derivatives lla-d from 377-azepines lOa-d upon reaction with bromine <2003H(60)2211> (Scheme 1). Unlike the situation observed with cycloheptatrienes, delocalized azatropylium salts were not formed from the reaction of 377-azepines with bromine in the absence of an alcoholic solvent. Reaction of 12 with bromine gave 13 plus the bis-ether 14 and bromomethane. The product 14 was also observed in the reaction of 12 with NBS (0.5 equiv) with 1 equiv of 7V-bromosuccinimide (NBS) 12 afforded the succinimido-substituted derivative 15, which upon elimination of HBr in the presence of base gave the 277-azepine 16 (Scheme 2) <2003H(60)2211>. 

When 7V-bromosuccinimide was used instead of l,3-dibromo-5,5-dimethylhydantoin, similar yields were achieved. Lilectron-rich aromatic rings undergo bromination. Thus, the desired products are obtained by dehalogcnation of the brominated products using palladium on charcoal as catalyst. 

Tellurium bis[dithiocarboxylates] lose one dithiocarboxylate group and form tellurium dithiocarboxylate halides in reactions with equimolar amounts of chlorine, bromine, iodine, iV-chlorosuccinimide, or 7V-bromosuccinimide in dichloromethane. ... 

In practice, few alkenes are soluble in water, and bromohydrin formation is often carried out in a solvent such as aqueous dimethyl sulfoxide, CHjSOCHj (DMSO), using a reagent called 7V-bromosuccinimide (NBS) as a source of Br2. NBS is a stable, easily handled compound that slowly decomposes in water to yield Brg at a controlled rate. Bromine itself can also be used in the addition reaction, but it is more dangerous and more difficult to handle than NBS. 

Substitution reactions resulting in formation of bromocyclopropanes via cyclopropyl radicals have been observed when bromine or 7V-bromoimides are used as brominating agents. Bro-mination of 9-cyclopropylanthracene was particularly successful when 7V-bromosuccinimide was employed 9-(l-bromocyclopropyl)anthracene (19) was isolated in 90% yield. 

Use of other halogenating agents, such as A -bromosuccinimide, under conditions where the chain-carrying radical was succinimidyl rather than bromine, resulted in a majority of attack in the side chain. However, the final abstraction of a bromine atom from 7V-bromosuccinimide was so rapid that j8-scission could not compete and unrearranged products accumulated. Similarly, in the reaction of A -bromo-3,3-dimethylglutarimide, or of 7V-bromophthaIimide (10), with methylcyclopropane (11), only unrearranged (bromomethyl)cyclopropane (12) could be isolated. ... 

In contrast to the parent cydopropa[a]naphthalene, its 1,1-dichloro- and 1.1-difluoro derivatives may be synthesized by a variation of the original Billups scheme. The respective dihalocar-benes were added to l-bromo-3,4-dihydronaphthalene. A bromo substituent was then introduced at C3 of 7 by benzylic bromination with 7V-bromosuccinimide, after which aromatization to the very labile cycloproparene products 8 was elTected under mild conditions. In this sequence, the halogens were situated in such a way that no exocyclic double bonds could be formed upon dehydrobromination. The problem of rearrangement of such a double bond into the six-membered ring is therefore circumvented. Both the dichloro and the difluoro derivatives 8 are very sensitive to moisture, and have only been observed in solution. 

Diels-Alder cycloaddition with, for example, butadiene <85JOC5604>. 7V-Bromosuccinimide can be used to oxidise the initial adduct formed between phthalazine-l,4-dione and 1,4-diphenyl butadiene via benzylic bromination and thermal elimination of hydrogen bromide the intermediate bromide is, however, very labile towards nucleophiles, and base causes cleavage of the phthaloyl residue, leaving 3,6-diphenylpyridazine <86JOC3123>. 

A jS-D-xylosidase of a thermophilic fungus, Malbranchea pulchella was purified 99-foId from the culture filtrate after ammonium sulphate fractionation, ion-exchange chromatography, column electrophoresis, and gel filtration. The purified enzyme was found to be homogeneous upon ultracentrifugal analysis, disc electrophoresis and gel filtration. The enzyme (mol. wt. 2.6 XlO" by gel filtration, 2.78 S, icm 280 nm = 13.2, pH optimum 6.2-6.8, temperature optimum 50 °C) was inhibited by Zn, Cu ", 7V-bromosuccinimide, 4-chloromercuribenzoate and sodium dodecyl sulphate, while this activity was activated by The enzyme released D-xylose as the end product even... 

The Wohl-Ziegler reaction is the reaction of an allylic or benzylic substrate with 7V-bromosuccinimide (NBS) under radical initiating conditions to provide the eor-responding allylie or benzylie bromide. Conditions used to promote the radieal reaction are typieally radical initiators, light and/or heat earbon tetrachloride (CCI4) is typieally utilized as the solvent. 

The endo-ester A is rapidly isomerized to the exo-isomer B in the presence of 7V-bromosuccinimide at 80°C. The compound is stable at this temperature in the absence of MBS. The saturated analog C shows no reactivity toward NBS. Suggest a mechanism for the isomerization. 

Oxidation of (— )-j3-hydrastine with 7V-bromosuccinimide results in cleavage of the alkaloid at the C-1 to C-9 bond, and formation of A -methyl-4-bromo-6,7-methylenedioxyisoquinoline. ... 

In some cases, oxidations of sterically hindered alcohols were slow under the standard conditions. However, by extending the reaction times and using 7V-bromosuccinimide instead of NCS, excellent yields of the ketone could still be obtained (eq 7). Also, alcohols which can form stabilized carbocations provide the aldehyde in low yields under the standard conditions (eq 8). In this case, the major product is the alkyl chloride. By using l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base instead of potassium carbonate, good yields of the aldehyde can be obtained (eq 9). 

Related Reagents. 7V-Bromosuccinimide Chloramine-T 7V-Chlorosuccinimide N-(l, 1-Dimethylethyl)benzenesulfinimi-doyl Chloride Tetrapropylammonium Perruthenate Dimethyl sulfoxide-oxalyl Chloride l,l,l-Triacetoxy-l,l-dihydro-l,2-benziodoxol-3(l/7)-one 2-Iodoxybenzoic Acid (IBX) Diphenyl Sulfoxide. 

Bromomethylthiophene was obtained by bromina-tion of 3-methylthiophene with 7V-bromosuccinimide in... 

Related Reagents. Bromine-r-Butylamine Bromine Chloride Bromine-l,4-Diazabicyclo[2.2.2]octane Bromine-1,4-Dioxane Bromine-Silver(I) Oxide Bromine-Triphenyl Phosphite iV-Bromosuccinimide A7-Bromosiiccinimide-Dimethylformamide 7V-Bromosuccinimide-Dimethyl Sulfide Al-Bromosuccinimide-Sodium Azide Copper(II) Bromide Hy-drobromic Acid Mercury(II) Oxide-Bromine Phosphoms(III) Bromide Pyridinium Hydrobromide Perbromide Sodium Bromide Thallium(III) Acetate-Bromine. 

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