29887-60-3

Basic information

• Product Name: 1,2-dimethoxycyclohexane
• Synonyms: Cyclohexane, 1,2-dimethoxy-, (1R,2R)-rel-
• CAS NO: 29887-60-3
• Molecular Formula: C₈H₁₆O₂
• Molecular Weight: 144.2114
• Mol File: 29887-60-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 175.5°C at 760 mmHg
• Flash Point: 50°C
• Density: 0.92g/cm³
• Vapor Pressure: 1.54mmHg at 25°C
• Refractive Index: 1.431
• CAS DataBase Reference: 1,2-dimethoxycyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dimethoxycyclohexane(29887-60-3)
• EPA Substance Registry System: 1,2-dimethoxycyclohexane(29887-60-3)

Safety Data

• Hazardous Substances Data: 29887-60-3(Hazardous Substances Data)

Upstream product

• 1460-57-7 trans-1,2-cyclohexandiol 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 54826-41-4 trans-1-iodo-2-methoxycyclohexane 
• 51533-22-3 trans-1-methoxy-2-phenylselenocyclohexane 
• 110-83-8 cyclohexene 
• 7429-37-0 trans-1,2-dibromocyclohexane 
• 124-41-4 sodium methylate 

Relevant articles and documents

Conformational analysis of cyclohexane-1,2-diol derivatives and MM3 parameter improvement

The positions of the equilibria between the diequatorial and diaxial conformers of trans-1,2-dimethoxycyclohexane (2) and trans-2-methoxycyclohexanol (3) have been measured accurately by13C n.m.r. spectroscopy at -80°C in a series of solvents r

The role of hydrogen migration in the mechanism of alcohol elimination from MH+ ions of ethers upon chemical ionization

An enhanced elimination of alcohol under isobutane CI conditions, resulting in highly abundant [MH - ROH]+ ions, has been observed in several primary and secondary ethers having a tertiary β-position (methine), as compared with those with β-methylene. This elimination exhibits a significant degree of stereospecificity in stereoisomeric 2-methyl-1-methoxycyclohexanes 4 and 1-methoxy-trans-decalins 7, affording more abundant [MH - ROH]+ ions in the cis isomers 4c and 7tc than in their trans counterparts 4t and 7tt. These findings suggest involvement of a 1,2-hydride migration from the β- to α-position in the course of the alcohol elimination from the MH+ ions of the above cis-ethers, resulting in tertiary carbocation structures. The proposed mechanism of alcohol elimination is supported by a considerable deuterium isotope effect detected in β-deuterium-labeled cis-2-methyl-1-methoxycyclohexane and by a CID study of the structures of [MH - ROH]+ ions obtained from cis- and trans-1,2-dialkoxycyclohexanes. Ring contraction by a Meerwein-type rearrangement has also been observed in the latter system.

Oxidatively Assisted Nucleophilic Substitution/Elimination of Alkyl Iodides in Alcoholic Media. A Further Study

Oxidation of a series of alkyl halides with alcoholic 3-chloroperoxybenzoic acid afforded the results outlined in Charts I-III and Tables I-III.The reaction was found to be a powerful and convenient method for effecting nucleophilic substitution in a variety of systems, including the highly inert 1- and 7-bicycloheptyl systems.Qualitatively, the number of molar equivalents of oxidant required varied inversely with the expected ease of substitution for a given system.A mechanism is suggested whereby the iodide is oxidized stepwise to a species RIOn in which n is an integer sufficiently large that the system in question will undergo nucleophilic substitution or elimination.Reaction in the presence of added chloride or bromide ion usually resulted in a facilitation of reaction rate and a decrease in the number of molar equivalents of oxidant required; the principal product under these conditions was usually the corresponding chloride or bromide.