50405-39-5

Usage

Uses

Used in Organic Synthesis:
1-Bromo-1-butyne is utilized as a key intermediate in organic synthesis for the production of various organic compounds. Its ability to engage in nucleophilic substitution and addition reactions makes it a valuable component in creating complex organic molecules.
Used in Chemical Reactions as a Reagent:
In the realm of chemical reactions, 1-Bromo-1-butyne serves as a reagent, facilitating specific transformations in organic molecules. Its reactivity with nucleophiles and its propensity for addition reactions are particularly useful in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1-Bromo-1-butyne is employed as a building block in the pharmaceutical industry for the synthesis of new drug candidates. Its unique reactivity allows for the creation of novel molecular structures with potential therapeutic applications.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 1-Bromo-1-butyne is used as a precursor in the development of new pesticides and other agricultural chemicals, contributing to the advancement of crop protection strategies.
Used in Specialty Chemicals Production:
1-Bromo-1-butyne is also utilized in the production of specialty chemicals, where its unique chemical properties are harnessed to create compounds with specific applications in various industries, such as materials science and coatings.

InChI:InChI=1/C4H5Br/c1-2-3-4-5/h2H2,1H3

Upstream product

• 73383-24-1 1,1-dibromo-3-methylprop-1-ene 
• 51207-09-1 1-butynyl magnesium bromide 
• 107-00-6 but-1-yne 

Downstream Products

• 71-36-3 butan-1-ol 
• 17229-76-4 2-propylbenzo[d]thiazole 
• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 
• 10508-66-4 hexa-1,3-diyn-1-ylbenzene 
• 71673-31-9 1,1-diethoxy-11,13-hexadecadiyne 
• 120569-51-9 hepta-2,4-diyn-1-ol 

Relevant academic research and scientific papers

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.

Synthesis of heteroaryl ketones via tandem reaction of 1,1-dibromoethenes

A novel method for the synthesis of heteroaryl ketones through one-pot tandem reaction of 1,1-dibromoethenes with 2-amino(thio)phenols promoted by TBAF·3H2O and RuCl3(5%)/air was developed. This novel method includes several reactions in one-pot and utilizes economical yet efficient reagents to generate synthetically and biologically interesting heteroaryl ketones under mild conditions with good efficiency.

SYNTHETIC NAVEL ORANGEWORM PHEROMONE COMPOSITION AND METHODS RELATING TO PRODUCTION OF SAME

One or more embodiments of the invention are directed to the synthetic methods for making lepidopteran pheromones including navel orangeworm pheromones. The synthetic methods involve novel, efficient, and environmentally benign steps and procedures.

Synthesis of enamides from aldehydes and amides

A range of double unsaturated amides (15, 19, and 21), obtained by cross-coupling reactions was reacted with aldehydes to hemiaminals. Heating the hemiaminals in the presence of Ac2O and pyridine affected clean conversion to the corresponding enamides, such as 42, 45, and 47. Alternatively, N,S-acetals were prepared which were oxidized to the sulfones. Treatment with base also gave the enamides, favoring the cis-isomer. However, this method is less general. Application of these methods led to the natural products lansiumamide-A (30_cis), lansiumamide-I (31) and lansiumamide-B (32).

A comparative study of the synthetic paths from 1-butyne to 2E,4Z-heptadien-1-ol

2E,4Z-Heptadien-1-ol (1), the key intermediate in the synthesis of the grapevine moth sex pheromone, was obtained from 1-butyne by a number of alternative procedures, including various variants of the stereocontrolled building of the conjugated E,Z-diene system (Cadiot-Chodkiewicz cross-coupling, alkyne-vinyl halide cross-coupling catalyzed by palladium complexes, anionotropic allylic rearrangement, partial cis- and trans-reduction of the triple bond).None of them could provide for configurational uniformity of 1.The most acceptable path to obtain 1 in multigram amounts appears to be that which proceeds via the conjugated diynol and enynol intermediates with subsequent catalytic cis-hydrogenation.

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.