40596-44-9

Usage

Uses

Used in Chemical Synthesis:
4-IODOBUTYL ACETATE is used as a reagent for the preparation of specific phosphonium iodides, such as tricyclohexyl(acetoxybutyl))phosphonium iodide and tri-n-hexyl(acetoxybutyl))phosphonium iodide. These phosphonium iodides are essential intermediates in the synthesis of various complex organic molecules and have potential applications in materials science and pharmaceuticals.
In the Chemical Industry:
4-IODOBUTYL ACETATE is used as a building block in the synthesis of complex organic molecules, contributing to the development of new compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
In the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-IODOBUTYL ACETATE could potentially be used in the pharmaceutical industry as an intermediate for the synthesis of drug candidates or as a reagent in the development of novel drug delivery systems, given its role in the synthesis of phosphonium iodides.
In the Materials Science Industry:
4-IODOBUTYL ACETATE may also find applications in the materials science industry, where the synthesized phosphonium iodides could be used to develop new materials with unique properties, such as improved conductivity, stability, or biocompatibility.

Synthesis Reference(s)

Synthetic Communications, 24, p. 951, 1994 DOI: 10.1080/00397919408020770

Synthesis

The synthesis of 4-IODOBUTYL ACETATE is as follows:Acetic acid (0.30mmol, 1.0 equivalent), CuI (0.03mmol, 10.0mol%, 5.7mg) and NaI (0.60mmol, 2.0 equivalent, 89.9mg) were added to a 10mL Schlenk tube equipped with a magnetic stirring device. Vacuum the flask with a pump and backfill it three times with nitrogen. Then, 1.0 mL tetrahydrofuran (12.30 mmol, 41.0 equivalence, 1 mL, c=0.30 M), deionized water (0.45 mmol, 1.5 equivalence) and TMSCF3 (0.36 mmol, 1.2 equivalence) were added under N2 atmosphere. The mixture is stirred at 150°C (thermostatic oil bath pot) for 12 hours. After cooling to room temperature, dilute the mixture with ethyl acetate (15 mL), wash with water and brine, and dry on anhydrousNa2SO4. After Extraction by EtOAc (5 mL x 3), the combined organic layer was dehydrated with anhydrousNa2SO4 and concentrated under reduced pressure. The crude product is purified by rapid chromatography on silica gel to obtain alkyl iodide.

InChI:InChI=1/C6H11IO2/c1-6(8)9-5-3-2-4-7/h2-5H2,1H3

Upstream product

• 109-99-9 tetrahydrofuran 
• 507-02-8 acetyl iodide 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 141947-88-8 lithium telluroacetate 
• 134-81-6 benzil 
• 628-67-1 butane-1,4-diol diacetate 

Downstream Products

• 296282-60-5 6-phenylhexyl acetate 
• 3208-25-1 7-phenylheptan-1-ol 
• 103-65-1 phenylpropane 
• 1087-49-6 1,6-diphenylhexane 
• 155446-29-0 1-acetoxy-7-phenylheptane 
• 157063-03-1 Acetic acid 4-(toluene-4-sulfonyl)-butyl ester 
• 7492-40-2 4-phenylbutyl acetate 
• 5048-30-6 1-acetoxy-6-heptene 
• 123-86-4 acetic acid butyl ester 
• 119649-85-3 Acetic acid 4-(3-oxo-cyclohexyl)-butyl ester 
• 37338-40-2 Δ⁸-Dodecenyl acetate 
• 213205-45-9 6-Acetoxy-2-acetyl-2-((Z)-2-benzenesulfonyl-1-bromomethyl-vinyl)-hexanoic acid tert-butyl ester 
• 1048998-74-8 ethyl 1-(4-acetoxybutyl)-6-(2,4-dichlorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 1048998-79-3 ethyl 1-(4-acetoxybutyl)-6-(2,4-dichlorobenzoyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes

Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.

Acyl iodides in organic synthesis: II. Reactions with acyclic and cyclic ethers

Reaction of acyl iodides RCOI (R = Me, Ph) was studied with acyclic and cyclic ethers (Et2O, MeCHCH2(O), ClCH2CHCH 2(O), THF, O(CH2CH2)2O, EtOCH 2CH2OH, EtOCH=CH2, PhOEt]. The reaction occurred with the rupture of one or two CO bonds furnishing the corresponding iodides and esters.

Highly regioselective cleavages and iodinations of cyclic ethers utilizing SmI2

Various functionalized cyclic ethers such as oxiranes, oxetanes, and tetrahydrofurans have been prepared, and the regiochemistry of their ring opening with samarium diiodide and acyl chloride or anhydride has been investigated. Alkyl-substituted oxetane 5 and tetrahydrofurans 1 and 2 show almost no regioselectivity. However, high regioselectivities from the branched cyclic ethers (3, 8, 9, and 10) containing ethereal or hydroxyl moieties have been observed. This is probably the result of the bidentate chelated species between samarium and oxygen.

Scavenger assisted combinatorial process for preparing libraries of tertiary amine compounds

This invention relates to a novel solution phase process for the preparation of tertiary amine combinatorial libraries. These libraries have utility for drug discovery and are used to form wellplate components of novel assay kits.

A remarkably simple process for monoprotecting diols

Lipase from pig pancreas (PPL) has been shown to catalyse selectively the hydrolysis of alkane-1,n-diol bis-acetates into the corresponding monoacetate.

A versatile approach to cyclic ethers. Synthesis of disubstituted oxepanes and oxocanes

A synthetic sequence for the preparation of α,α'-disubstituted cyclic ethers of various ring sizes and either relative stereochemistry (cis or trans) is presented. It is based on the hetero Diels Alder reaction of a monoactivated diene and an aldehyde, yi

Synthesis of novel pyridazine acyclonucleosides

Some pyridazine acyclonucleosides containing hydroxymethyl and 4-hydroxybutyl groups as an alkanol side chain were prepared. Nucleophilic displacement of N1-alkyl-4,5-dichloropyridazin-6-ones is discussed.

Synthesis of long chain ω-aralkylbromides

1-Iodo-4-acetoxybutane is a useful 4 carbon synthon which reacts selectively with Grignards under copper catalysis. The immediate products are converted to bromides.