73630-93-0

Usage

Chemical Properties

turbid yellow fuming liquid

InChI:InChI=1/C6H12BrN/c1-5(2)6(7)8(3)4/h1-4H3

Upstream product

• 26189-59-3 1-chloro-1-(dimethylamino)-2-methyl-1-propene 
• 21678-37-5 N,N,2-trimethylpropionamide 

Downstream Products

• 21678-37-5 N,N,2-trimethylpropionamide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Relevant academic research and scientific papers

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

A mild method for the replacement of a hydroxyl group by halogen: 2. unified procedure and stereochemical studies

N,N-Dimethyl- and N,N-diisopropyl-1-halo-2-methyl-l-propenylamines are readily available reagents for the mild deoxyhalogenation of alcohols and hydroxyacids. In this study we showed that the reactivity of the reagents can be tuned by varying the size of the alkyl groups on the reagents: the replacement of methyl by isopropyl groups led to a significant increase of reactivity. We then described a unified procedure for all deoxyhalogenations using the readily available α-chloroenamines as reagents with (bromination, iodination) or without (chlorination) an alkaline bromide or iodide. Finally, we showed that deoxyhalogenation reactions of secondary alcohols were highly stereospecific and generally occurred with inversion of configuration.

A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

NEURAMINIDASE INHIBITORS

Disclosed are neuraminidase inhibitor compounds and pharmaceutical compositions with improved bioavailability and/or improved efficacy and methods of treating influenza using the compounds and pharmaceuticals compositions.

A general and practical method of synthesis of 2-disubstituted-1- chloro- and 1-bromoenamines

Disubstituted-α-chloroenamines are useful synthetic intermediates which had earlier been prepared by the reaction of tertiary amides with phosgene. The toxicity of the latter led us to systematically investigate new synthetic routes towards α-chloro- and

Introduction of bromine and chlorine substituents in medium ring ethers and lactones

A convenient preparation of α-halo enamines using oxalyl halides is described together with applications of these reagents in the halogenation of β-hydroxy cyclic ethers and lactones.