57951-72-1

Usage

Uses

Used in Organic Synthesis:
1-Bromo-2-cyclopropylethyne is employed as a reagent in organic synthesis for its ability to participate in substitution and addition reactions. Its unique structure allows it to be a key component in creating a wide array of organic compounds.
Used in Chemical Research:
In the field of chemical research, 1-Bromo-2-cyclopropylethyne is used to explore and understand the mechanisms of various chemical reactions, contributing to the advancement of chemical knowledge and the development of new synthetic pathways.
Used in the Synthesis of Complex Organic Molecules:
As a building block, 1-Bromo-2-cyclopropylethyne is instrumental in the synthesis of complex organic molecules, where its reactivity and structural features are leveraged to construct molecules with specific properties and functions.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in organic synthesis and the creation of complex molecules, 1-Bromo-2-cyclopropylethyne may also find applications in the pharmaceutical industry for the development of new drugs and medicinal compounds.
Safety Considerations:

Upstream product

• 6746-94-7 Cyclopropylacetylene 

Downstream Products

• 1263053-70-8 N-(cyclopropylethynyl)-N,4-dimethylbenzenesulfonamide 
• 1400687-48-0 2-cyclopropyl-5-phenylpyrazolo[5,1-a]isoquinoline 
• 1400687-41-3 2-cyclopropyl-9-methyl-5-phenylpyrazolo[5,1-a]isoquinoline 
• 1437787-87-5 C₁₆H₁₇NO₂S 
• 1437788-03-8 C₁₆H₁₇NO₄S 
• 1437788-19-6 C₁₆H₁₇NO₃S 
• 1581883-42-2 (Z)-6-phenylsulfonyl-8-cyclopropyloct-5-en-7-yne 

Relevant academic research and scientific papers

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

Directed Nickel-Catalyzed pseudo-Anomeric C?H Alkynylation of Glycals as an Approach towards C-Glycoconjugate Synthesis

The synthesis of complex C-glycoconjugates is presented here using a key directed nickel-catalyzed C?H alkynylation step. Thanks to a bidentate amidoquinoline-type directing group, the insertion of diverse alkynyl moieties onto the pseudo-anomeric position of glycal substrates was performed on ten examples in moderate to good yields. These platforms were used as starting substrates in a click reaction with complex azides to form original C-glycoconjugates. By this route, a C-glycosylated amino acid, a C-linked disaccharide and a C-glycosylated biotin derivative were synthesized. Preliminary conditions to remove the directing group are also proposed. (Figure presented.).

Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides

In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and mor

A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.

Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light

A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.

A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems

A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured α-halo enamides via photocatalysis or under Sonogashira coupling conditions.

Gold-Catalyzed [4+2]- and [3+3]-Annulations of Ynamides with 1-Yn-3-ols to Access Six-Membered Carbocycles and Oxacycles via Three Distinct Cyclizations

Three distinct strategies for catalytic annulations between ynamides and 1-yn-3-ols are described; the resulting carbo- and heterocycles were produced efficiently in one-pot operations using a gold catalyst. The chemoselectivities of these annulations are controlled by variations of the substituents of the ynamides and the 1-yn-3-ols. This reaction sequence involves initial alkoxylations of ynamides, followed by Claisen rearrangement of propargylic enol ethers, and ends with 6-endo-trig cyclizations of 1-allenyl-5-amide intermediates. Among these cascade annulations, the cyclizations of 5-allenyl-1-amides to yield 5,6-dihydro-2-pyranones and 6-alkylenecyclohex-2-ene-1-carboxamides are unprecedented in the literature. (Figure presented.).

Borane-catalyzed selective hydrosilylation of internal ynamides leading to β-silyl (Z)-enamides

We have developed a borane-catalyzed regioand stereoselective hydrosilylation of internal ynamides for the first time. The scope of ynamide substrates and silane reactants was broad under mild reaction conditions, affording synthetically versatile β-silyl (Z)-enamide products. The observed stereoselectivity was reasoned to be due to the β-silicon effect on a postulated ketene iminium intermediate.

Synthesis of Highly Functionalized 4-Aminoquinolines

A diverse set of highly substituted 4-aminoquinolines was synthesized from ynamides, triflic anhydride, 2-chloropyridine, and readily accessible amides in a mild one-step procedure. Diverse products: Electrophilically activated amides easily react with sulfonyl ynamides to yield a diverse range of substituted 4-aminoquinolines. The ynamides can be easily modified by Sonogashira processes or generated from dichloroenamide precursors. Any substituent can thus be introduced at the C3 position of the quinoline. 2-ClPy=2-chloropyridine, Tf2O=triflic anhydride.

Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides to yield 1-amino-1H-indenes

Gold-catalyzed [3+2]-annulations of α-aryl diazonitriles with ynamides and allenamides yield 1-amino-1H-indenes in two distinct pathways; the success of these annulations relies on the high electrophilicity of α-cyano arylgold carbenes to activate an ionic pathway.