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

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

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

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

Trans dialkoxylation of cyclic alkenes: A Prevost-type reaction

Reaction of anhydrous silver perchlorate, sym-collidine, and iodine (2:1:1 molar ratio) with cyclic alkenes and an excess of an alcohol in CH 2Cl2 affords trans-1,2-dialkoxycycloalkanes in high yields and purity. The reaction occurs via initial formation of the trans-iodoethers, which undergo Ag-assisted iodide abstraction to give the trans-diethers. Georg Thieme Verlag Stuttgart.

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.

Photoinduced Electron Transfer Initiated Activation of Organoselenium Substrates as Carbocation Equivalents: Sequential One-Pot Selenylation and Deselenylation Reaction

The investigation presented in this paper explores the mechanistic aspects and synthetic potentials of PET activation of organoselenium substrates.Fluorescence quenching of 1DCN* by a number of organoselenium compounds (RCH2SeR', 1-4), correlation of the fluorescence quenching rate constants with the oxidation potentials of 1-4, and the dependence of photodissociation quantum yields of 1-4 on their concentration suggests the occurence of electron transfer processes between 1DCN* and 1-4.Steady-state photolysis of 1-4 in the presence of 1DCN* leads to the efficient one-electron oxidative heterolytic dissociation of the carbon-selenium bond to produce the carbocation (RCH2(1+) or equivalent) and radical-centered selenium species (R'Se(.)) via the intermediacy of cation-radical .Nucleophilic assistance in the fragmentation of (RCH2SeR')(1+.) by methanol has been suggested on the basis of products obtained from the control PET reaction of neopentyl phenyl selenide (8).The synthetic utility of these findings has been demonstrated for the deselenylation (Table 4) as well as one-spot sequential selenylation-deselenylation (Table 5) reactions.

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.