36839-67-5

Usage

InChI:InChI=1/C6H14O/c1-4-6(5-2)7-3/h6H,4-5H2,1-3H3

Upstream product

• 584-02-1 2-pentanol 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 67-56-1 methanol 
• 616-24-0 3-aminopentane 
• 25636-49-1 3,3-dimethoxypentane 
• 96-22-0 pentan-3-one 

Relevant academic research and scientific papers

Peter J Derrick and the Grand Scale ‘Magnificent Mass Machine’ mass spectrometer at Warwick

The value of the Grand Scale ‘Magnificent Mass Machine’ mass spectrometer in investigating the reactivity of ions in the gas phase is illustrated by a brief analysis of previously unpublished work on metastable ionised n-pentyl methyl ether, which loses predominantly methanol and an ethyl radical, with very minor contributions for elimination of ethane and water. Expulsion of an ethyl radical is interpreted in terms of isomerisation to ionised 3-pentyl methyl ether, via distonic ions and, possibly, an ion-neutral complex comprising ionised ethylcyclopropane and methanol. This explanation is consistent with the closely similar behaviour of the labelled analogues, C3H7CH2CD2OCH3 +. and C3H7CD2CH2OCH3 +., and is supported by the greater kinetic energy release associated with loss of ethane from ionised n-propyl methyl ether compared to that starting from directly generated ionised 3-pentyl methyl ether.

Direct methylation of primary and secondary alcohols by trimethyl phosphate to prepare pure alkyl methyl ethers

Primary and secondary alcohols and diols react autocatalytically with trimelhyl phosphate plus small amounts of polyphosphoric acid at 185°C to give the corresponding methyl ethers. High purity and good yields are achieved when the ether is distilled from the reaction mixture as it is formed. By controlled addition even low-boiling alcohols can be methylated successfully. The reaction mechanism is undetermined. Peroxide formation in ethers is inhibited by storage over 10 molal KOH. Pure isotropic optical crystals are used for refractometer calibration. Improved physical property and NMR data (1H and 13C) are reported for thirteen methyl ethers. Simple two-point linear extrapolation of NMR shifts (especially 13C) to infinite dilution produces highly reproducible δ°-values (to 0.01 ppm or better) which uniquely characterize a molecule even when unidentified and/or not isolated from a mixture. This capability appears not to have been recognized in the literature. Acta Chemica Scandinavica 1998.

Nucleophilic Displacement with Heterocycles as Leaving Groups. Part 16. Reactions of Secondary Alkyl Primary Amines with 5,6,8,9-Tetrahydro-7-phenyldibenzoxanthylium Trifluoromethanesulphonate to give Intermediates Solvolysing without Rearrangement

Representative secondary alkyl primary amines R1R2CHNH2 react with the title pyrylium cation in acetic acid, alcohols, phenols, and NN-dimethylaniline acting as nucleophilic solvents to give O- and C-(secondary alkyl) products.Absence of carbenium ion rearrangements is consistent with reaction via intimate ion-molecule pairs formed rapidly from the corresponding pyridinium cations.

Acid-induced 13C Nuclear Magnetic Resonance Chemical Shift Changes of Ether and Ester Carbon Atoms

13C N.m.r. chemical shifts of ehters dissolved in tetrachloromethane are displaced on addition of trifluoroacetic acid.The displacements result from independent interactions of the acid with the substrate oxygen atoms and alkyl residues.The structure-dependent and stereoselective shift changes are useful for signal assignments, structure determination, conformational analysis, assessment of the distribution of rapidly interconverting conformers of esters, and estimation of the relative basicity of ethers.

TRIMETHYLSILYL TRIFLATE IN ORGANIC SYNTHESIS

Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media.The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.