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Usage

Uses

Used in Organic Synthesis:
1-Pentynyl iodide is used as a reagent in organic synthesis for its ability to facilitate the formation of carbon-carbon and carbon-nitrogen bonds, which are crucial in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Pentynyl iodide is used as a building block for the synthesis of alkynes, which are key components in the development of various pharmaceutical compounds.
Used in Chemical Industry:
Similarly, in the chemical industry, 1-Pentynyl iodide is employed in the preparation of alkynes, contributing to the synthesis of a wide range of chemical products.
Safety Precautions:
Given its hazardous nature, 1-Pentynyl iodide requires careful handling. It is essential to follow proper safety precautions and handling procedures to minimize the risk of ingestion, inhalation, or skin and eye contact, which can lead to adverse health effects.

InChI:InChI=1/C5H7I/c1-2-3-4-5-6/h2-3H2,1H3

Upstream product

• 627-19-0 1-Pentyne 
• 75-16-1 methylmagnesium bromide 
• 60-29-7 diethyl ether 
• 6088-91-1 iododiacetylene 
• 624-74-8 diiodoacetylene 
• 77190-19-3 C₁₈H₁₅AsO*C₅H₇I 
• 69116-28-5 C₁₈H₁₅PS*C₅H₇I 
• 69116-26-3 C₁₈H₁₅OP*C₅H₇I 
• 85121-06-8 C₆H₁₈N₃OP*C₅H₇I 
• 77190-55-7 3-Methyl-pyridine; compound with 1-iodo-pent-1-yne 

Downstream Products

• 16387-71-6 deca-4,6-diyne 
• 77190-19-3 C₁₈H₁₅AsO*C₅H₇I 

Relevant academic research and scientific papers

Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.

Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide

An efficient synthesis of 1-iodoalkynes and iodophenols was easily achieved by employing simple KI and TBHP. The reaction does not involve the use of a metal and base combination. A variety of substituted alkynes and phenols were prepared with good to excellent yield.

Improved syntheses of methyl (14E)- and (14Z)-dehydrocrepenynate: Key intermediates in plant and fungal polyacetylene biosynthesis

Efficient syntheses of the (14E)- and (14Z)-isomers of methyl dehydrocrepenynate have been achieved. The key steps involve Pd-catalyzed cross-coupling reactions furnishing the C=C double bonds between C14 and C15, followed by Wittig reactions to construct the (Z)-alkene at C9. High overall yields and stereoselectivities were achieved for both isomers.

Unsymmetrically substituted aliphatic diacetylenes

A general method for the synthesis of pure samples of unsymmetrically disubstituted diacetylenes of the type CH3-(CH2)(n)-C=C=C=C-CH2-OH (n=2,3,4,5) is described in detail. The materials could be polymerized thermally, in the liquid state.

Terminal 1-halo and 1-pseudohalo-1-alkynes via Bis(trimethylsilyl)peroxide (BTMSPO) promoted Umpolung transfer of halides and pseudohalides

Reaction of terminal acetylenes with readily available and inexpensive copper and zinc halides and pseudo-halides and BTMSPO has been found to be an effective and general route for obtaining, in the absence of bases and under mild conditions, 1-halo and 1-pseudohalo-1-alkynes in generally good yields.

Oxidative Decarboxylation of Propiolic Acids

The combination of iodine and iodine pentoxide in methanol was used to convert phenylpropiolic acid and 2-hexynoic acid to the corresponding ketal esters of one less carbon.In both cases, iodoacetylenic compounds were shown to be intermediates.In the case of the phenylpropiolic acid, a diiodoalkene was isolated and shown to be a second intermediate.

1-Iodoacetylenes. Part 2. Formation Constants of their Complexes with Lewis Bases

Formation constants of the complexes of 1-iodoacetylenes (1)-(8) with Lewis bases (9)-(15) have been measured in solution by i.r. spectrophotometry.The stoichiometry of the complexes, the influence of the solvent on the equilibrium position, the existence of linear free energy relationships in the series of iodinated Lewis acids RI, where R=I, Br, Cl, CN, and CCX, and the relation between i.r. frequency shifts and stability constants are discussed.With any electron donor, 1-iodoacetylenes form less stable complexes than those formed by iodine cyanide.With hard bases, iodocyanoacetylene (8) and ethyliodopropiolate (7) give complexes wich are, respectively, more stable than and as stable as those with iodine; however, iodine complexes with soft bases are more stable.This is rationalized, in terms of empirical acidity scales, by the necessity to correlate the thermodynamic and spectroscopic properties of the RI complexes by a double scale equation.