7541-16-4

Basic information

• Product Name: methyl dimethylcarbamate
• Synonyms: Carbamic acid, dimethyl-, methyl ester; Methyl dimethylcarbamate
• CAS NO: 7541-16-4
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.1198
• Mol File: 7541-16-4.mol

Chemical Properties

• Boiling Point: 100.4°C at 760 mmHg
• Flash Point: 14.5°C
• Density: 0.979g/cm³
• Vapor Pressure: 36.7mmHg at 25°C
• Refractive Index: 1.409
• CAS DataBase Reference: methyl dimethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl dimethylcarbamate(7541-16-4)
• EPA Substance Registry System: methyl dimethylcarbamate(7541-16-4)

Safety Data

• Hazardous Substances Data: 7541-16-4(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 4137-10-4 DIMCARB 
• 75-91-2 tert.-butylhydroperoxide 
• 96140-01-1 dimethoxy(dimethylamino)deuteromethane 
• 88470-22-8 N-Methoxy-N-chloro-N',N'-dimethylurea 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 2143-68-2 methoxyl radical 
• 68-12-2 N,N-dimethyl-formamide 
• 105157-41-3 C₆H₁₁ClN₂O₄ 
• 1283076-09-4 hexamethylguanidinium methylcarbonate 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 50-00-0 formaldehyd 
• 624-83-9 methyl isocyanate 
• 14442-54-7 methyl-nitro-carbamic acid methyl ester 

Relevant articles and documents

Pentaalkylmethylguanidinium methylcarbonates - Versatile precursors for the preparation of halide-free and metal-free guanidinium-based ILs

Pentaalkylmethylguanidinium methylcarbonates 6 can easily be prepared from pentaalkylguanidines 5 and dimethyl carbonate (DMC) in a sustainable solvent-free synthesis. Most of the title compounds are room temperature ionic liquids (RTILs) which provide convenient access to halide-free guanidinium-based ILs (GILs) 7via acid-base reactions and subsequent decarboxylation, similar to industrially important imidazolium methylcarbonates 1. The Royal Society of Chemistry.

On the Dynamic Structure Behaviour of the Dimethylamine-Carbondioxide Complex (Dimcarb)

Dimcarb, a liquid distillable 1.8:1-dimethylamine-carbondioxide complex which can be used as a preparatively profitable dimethylamine source, displays unusual properties in view of a salt ("dimethylammonium dimethylcarbamate").The dynamic structure behaviour has been investigated by 1H, 13C, and 15N NMR spectroscopy: At ambient temperature dimcarb underlies a rapid dimethylamine change between ammonium and carbamate functionality (ΔG(excit.) about 58 kJ/mol).On further temperature decreasing prototropic interactions between dimethylammonium and dimethylamine as well as dimethylcarbamate and dimethylcarbamic acid species are additionally revealed.Timely averaged, ionic structures predominate, obviously dimethylammonium dimethylcarbamate combinations as intimate ion pairs.Involved dimethylcarbamic acid can be trapped as methylester in high yield by reaction of dimcarb with diazomethane.Moreover, the dimethylcarbamic acid trimethylsilylester, obtained from dimcarb with the aid of trimethylchlorosilane, affords a crystalline product by methanolysis at -78 deg C, probably dimethylcarbamic acid, which decomposes above -50 deg C under carbondioxide elimination and regeneration of dimcarb. - Keywords: NMR Spectra, Dimethylamine, Carbondioxide, Dimethylammonium Dimethylcarbamate, Dimethylcarbamic Acid

THE KINETIC ISOTOPE EFFECT IN THE RADICAL FRAGMENTATION OF LINEAR ORTHO ESTERS

The substitution of hydrogen atoms of deuterium in triethoxymethane leads to a change in the formation rate of diethyl carbonate and ethyl formate.The magnitude of the kinetic isotope effect lies in the range of 2-3 and coincides with the known values for the free-radical reactions of linear and cyclic acetals.

FREE-RADICAL REACTIONS OF N,N-DIMETHYLAMINODIALKOXYMETHANES

The homolytic liquid-phase reactions of N,N-dimethylaminodialkoxymethanes, initiated by tert-butoxyl radicals in the range of 120-150 deg C, were investigated.The mechanism of the unbranched chain process of fragmentation of the acetals with quadratic chain termination at the alkyl radicals was determined.As a result the corresponding dimethylcarbamic esters, dimethylformamide, alkanes, and carbonyl compounds were formed.The relative rate constants for the transformations of the nitrogen analogs of the ortho esters were calculated.The difference in the activation energies for the cleavage of the C-H bonds adjacent to one and three heteroatoms was determined for N,N-dimethylaminodimethoxymethane (ΔE=5 kcal/mole) and N,N-dimethylaminodipentyloxymethane (ΔE=8 kcal/mole).

Direct vs. Indirect Mechanisms in Organic Electrochemistry. Estimates of Activation Energies for Hydrogen Atom Transfer Processes of Relevance in Indirect Mechanisms Using the Bond Energy-Bond Order (BEBO) and Equibonding Methods

Activation energies for a number of hydrogen abstraction reactions of interest in mechanistic organic electrochemistry have been calculated using the bond energy-bond-order (BEBO) and equibonding method.The main emphasis has been put on processes with bearing on the problem of deciding between direct and indirect mechanisms in anodic oxidation, viz. acyloxylation, hydroxylation, methoxylation, nitrooxylation, cyanation, carbomethoxylation and azidation.The results indicate that indirect mechanisms might play a more important role than presently assumed.