62199-52-4

Usage

Classification

Cycloalkane

Ring structure

Five-carbon ring (Cyclopentane)

Substituents

Two butyl groups

Position of butyl groups

1 and 2 positions on the ring

Physical state

Colorless liquid at room temperature

Primary use

Solvent in various industrial applications

Toxicity

Low toxicity

Environmental impact

Relatively environmentally friendly compared to other solvents

Commercial use

Limited

Importance

Significant in the study of cycloalkane chemistry and organic synthesis

Upstream product

• 123-38-6 propionaldehyde 
• 79058-72-3 {[(E)-2-But-2-en-(Z)-ylidene]-cyclopentylmethyl}-triphenyl-phosphonium; bromide 
• 111-69-3 hexanedinitrile 
• 79058-86-9 1-<2-(Triphenylphosphoranyliden)ethyliden>-2-<(triphenylphosphoranyliden)methyl>cyclopentan 
• 79058-77-8 Triphenyl<2-(2-ethyliden)cyclopentylmethyl>phosphoniumbromid 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 100544-15-8 1-butyl-2-butylidenecyclopentane 
• 1292288-89-1 (Z)-9-tridecen-5-ol 
• 1292288-90-4 O-phenyl O-(Z)-9-tridecen-5-yl thionocarbonate 
• 64275-75-8 (Z)-non-5-en-1-ol 
• 934-42-9 2-butylcyclopentanone 
• 2277-17-0 (Z)-5-nonenal 

Relevant academic research and scientific papers

Treasures from the Free Radical Renaissance Period - Miscellaneous hexenyl radical kinetic data

Rate constant data and Arrhenius parameters have been determined for a series of substituted hexenyl radicals of differing electronic and steric demand. Electron-withdrawing groups (CF3, CO2Et) directly attached to the radical centre slighly accelerate 5-exo ring-closure (k cis + ktrans ～ 2.1 × 105 s -1 at 25°) relative to donating groups (OMe; 1.6 × 10 5 s-1 at 25°). Sterically demanding groups (tert-Bu), as expected, slow the cyclization process (1 × 105 s -1). These observations are consistent with subtle changes in activation energy for 5-exo ring-closure. Interestingly, the nature of the solvent would appear to have a significant influence on this chemistry with the cis/trans stereoselectivity sometimes improved as the solvent polarity is increased. Except for the system containing the CF3 (electron-withdrawing) group which displays an increase in the cyclization/capture rate constant (kc/kH), a general decrease in the kc/kH ratio as solvent polarity is increased is noted; these changes have been speculated to arise mainly from changes in kH in the various solvents employed.

Open-chain and Cyclic Bis-phosphoranes from α,ω-Dinitriles, Diisobutylaluminium Hydride, and Methylenetriphenylphosphorane

The reaction of subero-, azelao-, and sebaconitrile (4, n = 6, 7, and 8) with diisobutylaluminium hydride (to give 5) and subsequenly with methylenetriphenylphosphorane leads to the openc-hain bis-phosphoranes 8 a-c, which have been characterized by the Wittig reaction.The same reaction sequence applied to adiponitrile produces the cyclic bis-phosphorane 9a.The previously unknown hydrocarbon 1,3,9,11-cyclohexadecatetraene (12) has been prepared from 8a and adipoaldehyde.