2003-82-9

Usage

Uses

Used in Organic Synthesis:
1-Bromoprop-1-yne serves as a valuable building block in organic synthesis, where it is utilized for the preparation of a wide array of compounds. Its reactivity allows for the creation of new chemical entities that can be tailored for specific purposes.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-Bromoprop-1-yne is employed in the synthesis of various drugs. Its unique chemical properties enable the development of new medicinal compounds with potential therapeutic benefits.
Used in Agrochemical Manufacturing:
1-Bromoprop-1-yne also finds application in the production of agrochemicals, contributing to the development of pesticides and other agricultural products that are essential for crop protection and yield enhancement.
Used in Rubber and Plastics Industry:
1-bromoprop-1-yne is utilized in the manufacturing processes of rubber and plastic products, where it may contribute to the formation of specific material properties or serve as a component in the production of polymers.
Safety Note:
It is crucial to handle 1-Bromoprop-1-yne with care due to its toxic and flammable nature. Adequate safety measures, including proper personal protective equipment and handling procedures, should be strictly adhered to in order to prevent accidents and ensure the safety of individuals working with this chemical.

Upstream product

• 14602-62-1 1,1,2-tribromo-propane 
• 74-99-7 prop-1-yne 
• 7726-95-6 bromine 
• 53210-70-1 silver(I) propynyde 
• 13195-80-7 1,1-dibromopropene 

Downstream Products

• 1595-67-1 1-<4-Chlor-phenyl>-hexadiin-(2,4)-ol-(1) 
• 1595-65-9 1-p-Methoxyphenylhexa-2,4-di-in-1-ol 
• 1595-58-0 1-p-Dimethylaminophenylhexa-2,4-di-in-1-ol 
• 1595-57-9 1-p-Carboxyphenylhexa-2,4-di-in-1-ol 
• 15375-63-0 1-Diphenylamino-hexadiin-(2.4) 
• 4009-22-7 agropyrene 
• 1574-95-4 1-phenyl-2,4-hexadiyn-1-ol 
• 127357-38-4 N-(benzyloxycarbonyl)-α-hydroxy-glycine methyl ester 
• 119839-50-8 methyl 2-amino-N-(benzyloxycarbonyl)-3-pentynoate 
• 126403-76-7 2-Amino-3-prop-1-ynyl-benzonitrile 
• 19491-25-9 allene-d₁ 
• 73341-19-2 propyne-3d₁ 
• 75606-29-0 2-But-2-ynylsulfanyl-ethylamine 
• 869191-68-4 1,3-dibromo-2-propene 

Relevant academic research and scientific papers

The Hexadehydro-Diels-Alder Cycloisomerization Reaction Proceeds by a Stepwise Mechanism

We report here experiments showing that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction proceeds in a stepwise manner - i.e., via a diradical intermediate. Judicious use of substituent effects was decisive. We prepared (i) a series of triyn

Hexadehydro-Diels-Alder (HDDA)-Enabled Carbazolyne Chemistry: Single Step, de Novo Construction of the Pyranocarbazole Core of Alkaloids of the Murraya koenigii (Curry Tree) Family

Here we report the use of the hexadehydro-Diels-Alder (HDDA) reaction for the de novo construction of a benzenoid ring in fused polycyclic heteroaromatic carbazole (i.e., [2,3]-benzoindole) skeletons. The strategy allows creation of highly substituted benzenoids. We also describe the HDDA-enabled chemical synthesis of the natural product alkaloids mahanimbine and koenidine. Trapping of the intermediate carbazolyne with a conjugated enal, proceeding through formal [2+2] cycloaddition, 4π-electrocyclic ring opening, and 6π-electrocyclic ring-closing events, constitutes a robust method for producing pyranocarbazoles.

Practical and safe procedures for the preparation of the lower homologues of bromoacetylene

The lower homologues of bromoacetylene, from 1-bromopropyne to 1-bromo-1-hexyne, have been prepared in excellent yield by stirring the alkyne (in the cases of 1-propyne and 1-butyne a dilute solution in high-boiling petroleum ether) with a very concentrated aqueous solution of potassium hypobromite and potassium hydroxide.

Synthesis of 1,3-Diynes via Cadiot-Chodkiewicz Coupling of Volatile, in Situ Generated Bromoalkynes

A convenient Cadiot-Chodkiewicz protocol that facilitates the use of low molecular weight alkyne coupling partners is described. The method entails an in situ elimination from a dibromoolefin precursor and immediate subjection to copper-catalyzed conditions, circumventing the hazards of volatile brominated alkynes. The scope of this method is described, and the internal 1,3-diyne products are preliminarily evaluated in ruthenium-catalyzed azide-alkyne cycloadditions.

Reactions of HDDA-Derived Benzynes with Sulfides: Mechanism, Modes, and Three-Component Reactions

We report here reactions of alkyl sulfides with benzynes thermally generated by the hexadehydro-Diels-Alder (HDDA) cycloisomerization. The initially produced 1,3-betaine (o-sulfonium/aryl carbanion) undergoes intramolecular proton transfer to generate a more stable S-aryl sulfur ylide. This can react in various manners, including engaging weak acids (HA) in the reaction medium. This can produce transient ion pairs ArSR2+A- that proceed to the products ArSR + RA. When cyclic sulfides are used, A- opens the ring and is incorporated into the product, an outcome that constitutes a versatile, three-component coupling process.

Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy

The first total synthesis of (±)-gelsenicine is reported. The synthetic route is highly efficient (13 steps), featuring (1) a pivotal metal-catalyzed isomerization/rearrangement process that forges the central core of the molecule and (2) two facile C-N bond-forming steps that establish the flanking heterocycles.

Halogenation of alkynes and alkynylsilanes

Halogenation of alkynes has given 1,2-dihalogenoalkenes in good yields.Bromination of alkynylsilanes has given 1,2-dibromovinylsilanes, and reactions with iodine chloride mainly iodoalkynes.