93362-54-0

Usage

Uses

Used in Organic Synthesis:
N-(TRIISOPROPYLSILYL)-3,4-DIBROMOPYRROLE is used as an intermediate in organic synthesis for the preparation of a wide range of organic compounds. Its unique structure and reactivity make it a valuable component in the synthesis of various molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(TRIISOPROPYLSILYL)-3,4-DIBROMOPYRROLE is used as a building block for the development of complex organic molecules with potential therapeutic applications. Its versatility in organic synthesis allows for the creation of diverse chemical entities with specific biological activities.
Used in Chemical Research:
N-(TRIISOPROPYLSILYL)-3,4-DIBROMOPYRROLE is also utilized in chemical research to explore its reactivity, properties, and potential applications in various chemical reactions. Researchers use N-(TRIISOPROPYLSILYL)-3,4-DIBROMOPYRROLE to investigate new synthetic routes and develop innovative methodologies in organic chemistry.
Used in Material Science:
In the field of material science, N-(TRIISOPROPYLSILYL)-3,4-DIBROMOPYRROLE can be employed as a precursor for the synthesis of novel materials with unique properties. Its incorporation into polymers, coatings, or other materials can lead to the development of advanced materials with specific applications in various industries.

Upstream product

• 87630-35-1 N-triisopropylsilylpyrrole 
• 93362-20-0 2,3,4-tribromo-1-(triisopropylsilyl)pyrrole 
• 13154-24-0 triisopropylsilyl chloride 
• 87630-36-2 3-bromo-1-triisopropylsilanyl-1H-pyrrole 

Downstream Products

• 132034-60-7 (4-Bromo-1-triisopropylsilanyl-1H-pyrrol-3-yl)-diphenyl-methanol 
• 132034-58-3 (4-Bromo-1-triisopropylsilanyl-1H-pyrrol-3-yl)-phenyl-methanol 
• 773851-40-4 3-bromo-4-(4-methoxyphenyl)-1-(triisopropylsilyl)pyrrole 
• 2048-10-4 3,4-bis (4-methoxyphenyl)-1H-pyrrole 
• 773851-42-6 4-(4-methoxy-phenyl)-1-triisopropylsilanyl-1H-pyrrole-3-carbaldehyde 
• 773851-44-8 2,2,2-trifluoro-1-[4-(4-methoxy-phenyl)-1-triisopropylsilanyl-1H-pyrrol-3-yl]-ethanone 
• 132034-67-4 (4-Methyl-1-triisopropylsilanyl-1H-pyrrol-3-yl)-phenyl-methanol 
• 132034-69-6 (4-Methyl-1-triisopropylsilanyl-1H-pyrrol-3-yl)-diphenyl-methanol 
• 949529-69-5 C₃₀H₁₂Br₁₂N₆ 

Relevant academic research and scientific papers

Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls

As part of a program to develop practical syntheses of members of the family of (bacterio)chlorophylls, two routes to 2-iodo-3-methyl-4-(3-methoxy-1,3-dioxopropyl)pyrrole, a precursor of the universal ring C, have been developed. The β-ketoester of ring C

3,4-Ferrocenyl-functionalized pyrroles: Synthesis, structure, and (spectro)electrochemical studies

The synthesis of 3,4-diferrocenyl-substituted pyrroles of the type 3,4-Fc2-cC4H2NR [Fc = Fe(η5- C5H4)(η5-C5H5); R = Ph (3a), SO2-4-MeC6/sub

3,4-ferrocenyl-functionalized pyrroles: Synthesis, structure, and (spectro)electrochemical studies

The synthesis of 3,4-diferrocenyl-substituted pyrroles of the type 3,4-Fc2-cC4H2NR [Fc = Fe(η5-C5H4)(η5-C5H5); R = Ph (3a), SO2-4-MeC6

2,3,17,18-Tetrahalohexaphyrins and the first phlorin-type hexaphyrins

1-(Triisopropylsilyl)-3,4-dichloropyrrole and 1-(triisopropylsilyl)-3,4- difluoropyrrole were conveniently prepared from the corresponding 3,4-dibromopyrrole by lithiation followed by halogenation. 2,3,17,18- Tetrahalogeno [26]- and [28]hexaphyrins have b

Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respe

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).

A CONVENIENT METHOD FOR THE SYNTHESIS OF UNSYMMETRICAL 3,4-DISUBSTITUTED PYRROLES

A simplified procedure for the synthesis of 3,4-dibromo-1--1H-pyrrole (2) is described together with its sequential halogen-metal exchange chemistry to afford 3,4-disubstituted pyrroles.

3-Lithiopyrroles by Halogen-Metal Interchange of 3-Bromo-1-(triisopropylsilyl)pyrroles. Synthesis of Verrucarin E and Other 3-Substituted Pyrroles.

3-Lithio-1-(trimethylsilyl)pyrrole (7, Scheme 2), obtained by halogen-metal interchange from the 3-bromo compound 2, reacted with various electrophilic reagents to provide products, which on fluoride ion desilylation, gave 3-substituted pyrroles in good overall yields.One such pyrrole 13 (Scheme 3), was converted into 2-formyl-3-octadecylpyrrole (14), reputed to be a metabolite of the marine sponge Oscarella lobularis. 3,4-Dibromo-1-(triisopropylsilyl)pyrrole (5) was efficiently transformed, by a process involving two conscutive bromine-lithium exchange reactions (Scheme 4), into the antibiotic verrucarin E 17.