7260-94-8

Basic information

• Product Name: N,N-Dimethylcarbamic acid
• Synonyms: Dimethylcarbamic acid;N,N-Dimethylcarbamic acid
• CAS NO: 7260-94-8
• Molecular Formula: C₃H₇NO₂
• Molecular Weight: 89.09318
• Mol File: 7260-94-8.mol

Chemical Properties

• Boiling Point: 144.7°C at 760 mmHg
• Flash Point: 41.3°C
• Appearance: /
• Density: 1.114g/cm³
• Vapor Pressure: 2.83mmHg at 25°C
• Refractive Index: 1.444
• PKA: -1.67±0.12(Predicted)
• CAS DataBase Reference: N,N-Dimethylcarbamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylcarbamic acid(7260-94-8)
• EPA Substance Registry System: N,N-Dimethylcarbamic acid(7260-94-8)

Safety Data

• Hazardous Substances Data: 7260-94-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H7NO2/c1-4(2)3(5)6/h1-2H3,(H,5,6)

Upstream product

• 124-38-9 carbon dioxide 
• 4137-10-4 DIMCARB 
• 64-17-5 ethanol 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 150-68-5 monuron 
• 19937-59-8 metoxuron 
• 101-42-8 fenuron 
• 34123-59-6 N-(4-isopropylphenyl)-N',N'-dimethylurea 
• 330-54-1 DCMU 
• 15545-48-9 N-(3-chloro-4-methylphenyl)-N,N-dimethylurea 
• 7244-70-4 4-nitrophenyl dimethylcarbamate 

Downstream Products

• 124-38-9 carbon dioxide 
• 4137-10-4 DIMCARB 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 

Relevant articles and documents

Inorganic anionic oxygen-containing α-nucleophiles - Effective acyl group acceptors: Hydroxylamine ranks first among the α-nucleophile series

Comparative analysis of the nucleophilicity of inorganic oxygen-containing α-nucleophiles (hydroxylamine and ClO-, BrO--, HOO--, NH2O-, and F- ions) covering the pKa range from -2 to 13.81 toward 4-nitrophenyl esters (4-nitrophenyl acetate, 4-nitrophenyl p-toluenesulfonate, diethyl 4-nitrophenyl phosphate, ethyl 4-nitrophenyl ethylphosphonate, and 4-nitrophenyl dimethylcarbamate) in water at 25°C (ionic strength μ 1.0, KCl) was performed in terms of the extrathermodynamic Brosted relation. It was found for the first time that hydroxylamine anion ranks first among the series of α-nucleophiles. It is more reactive than HOO- ion with respect to 4-nitrophenyl acetate (by a factor of ～8), 4-nitrophenyl p-toluenesulfonate (by a factor of ～4) and 4-nitrophenyl dimethylcarbamate (by a factor of ～10). The nucleophilicities of HOO- and NH 2O- ions toward diethyl 4-nitrophenyl phosphate and ethyl 4-nitrophenyl ethylphosphonate are comparable. Taking into account that neutral hydroxylamine exhibits an anomalously high reactivity, as compared to not only common organic but also inorganic α-nucleophiles, it may be regarded as a unique α-nucleophile. Both neutral hydroxylamine and its anion as O-nucleophiles ensure high rates of acyl group transfer throughout a wide range of pH.

Phenylureas. Part 1. Mechanism of the basic hydrolysis of phenylureas

The mechanism of the hydrolytic decomposition of phenylureas in basic media in the pH range 12 to 14 is investigated. In this pH range a levelling of the rate-pH curve is observed as well as a change of the substituent influence on the hydrolysis rate. These experimental findings suggest the formation of an unreactive side product of the phenylurea in a parasitic side equilibrium at sufficiently high pH. The urea dissociates at the aryl-NH group to give its conjugate base. For the hydrolytic decomposition of phenylureas an addition-elimination mechanism is proposed as has been established for the alkaline hydrolysis of carboxylic acid esters and amides.

Correlation of the Rates of Solvolysis of N,N-Dimethylcarbamoyl Chloride

A correlation, using the extended Grunwald-Winstein equation, of the specific rates of solvolysis of N,N-dimethylcarbamoyl chloride in 21 solvents at 25.0°C demonstrates an appreciable sensitivity toward changes in both solvent ionizing power (YCl) and solvent nucleophilicity (NT), with an m value of 0.74 and an / value of 0.61.

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