17200-53-2

Usage

Uses

Used in Polymer Industry:
2-(Bromomethyl)acrylonitrile is used as a monomer for the synthesis of radically photopolymerizable compositions. Its application is particularly valuable because it contributes to the development of materials with high sensitivity and storage stability, which are crucial for various industrial applications, including coatings, adhesives, and printing inks.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-(Bromomethyl)acrylonitrile, due to its reactive nature, could potentially be used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form covalent bonds with other molecules makes it a candidate for the development of new drugs or drug delivery systems.
Used in Chemical Synthesis:
2-(Bromomethyl)acrylonitrile can also be utilized as a building block in the synthesis of various organic compounds, such as dyes, agrochemicals, and other specialty chemicals. Its reactivity allows for the creation of a wide range of products with different applications across multiple industries.

Upstream product

• 7659-44-1 2-(chloromethyl)acrylonitrile 
• 23873-54-3 2-(hydroxymethyl)-acrylonitrile 
• 126-98-7 methacrylonitrile 

Downstream Products

• 119813-66-0 2-((phenylsulfonyl)methyl)acrylonitrile 
• 63909-24-0 2-methylene-4-phenylbutanenitrile 
• 1312776-16-1 5-bromo-5-cyclohexylidene-2-methylenepentanenitrile 

Relevant academic research and scientific papers

Chain extension of aldonolactones by samarium iodide mediated Dreiding- Schmidt reactions and samarium assisted Imamoto reactions

Unprecedented SmI2 mediated Dreiding-Schmidt reactions were used for chain extension reactions of aldonolactones with alkyl 2-bromomethyl acrylates or 2-bromomethyl-acrylonitrile, respectively. The reaction of aldonolactones with diiodomethane

Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines

A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.

Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer

We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst

Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes

A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.

Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects

A case study on the polarity effects of radical mediated intermolecular alkene aminoallylation is presented herein. This radical group transfer method pairs vinyl ethers with electronically deficient allyl-oxyphthalimide derivatives to give difunctionalized products while illustrating the guiding effects of polarity on this radical reactivity.

Gram-Scale Synthesis of the (?)-Sparteine Surrogate and (?)-Sparteine

An 8-step, gram-scale synthesis of the (?)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (?)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.

FREE-STANDING NON-FOULING POLYMERS, THEIR COMPOSITIONS, AND RELATED MONOMERS

Free-standing non-fouling polymers and polymeric compositions, monomers and macromonomers for making the polymers and polymeric compositions, objects made from the polymers and polymeric compositions, and methods for making and using the polymers and polymeric compositions.

C-H Bond Functionalization with the Formation of a C-C Bond: A Free Radical Condensation Reaction Based on the Phthalimido-N-oxyl Radical

The development of a new chemical process that effects the conversion RH + C=C-C-X → R-C-C=C + HX, in which X is the phthalimido-N-oxyl radical (PINO·), is reported. The reaction yields are high, mass balances are excellent, and C-H bond functionalization and C-C bond formation are achieved in a single transformation. The byproduct of the reaction, N-hydroxyphthalimide, precipitates from solution and can be easily removed by simple filtration (and recycled). The kinetic chain lengths are shorter and the reaction times are longer (relative to those of the analogous reactions of allyl bromides), most likely because PINO· is a less-reactive hydrogen-atom abstractor. There appears to be no significant difference in efficiency in the addition-elimination steps. Competition experiments reveal that Br· and PINO· are comparable in leaving group ability.

Regioselective radical bromoallylation of allenes leading to 2-bromo-substituted 1,5-dienes

The regioselective radical bromoallylation of allenes proceeded efficiently in the presence of AIBN as a radical initiator to give 2-bromo-substituted 1,5-dienes in excellent yields. The addition of a bromine radical took place regioselectively onto the central carbon of allenes generating a stable allyl radical, which underwent addition/β-fragmentation reactions with allylbromides. The products could be further functionalized by Pd-catalyzed coupling reactions.

Unexpected electrophilic rearrangements of amides: A stereoselective entry to challenging substituted lactones

"Chemical Equation Presented" Surprise, surprise! An unexpected skeletal rearrangement was developed into a chemo- and stereoselective synthesis of aallyl and allenyl lactones with challenging substitution patterns (see scheme; EWC = electron-withdrawing group). The generality, unique features, and synthetic potential of this reaction were probed and a mechanism was proposed.