4137-10-4

Basic information

• Product Name: DIMCARB
• Synonyms: DIMCARB;DIMETHYLAMINE CARBON DIOXIDE COMPLEX;DIMETHYLAMMONIUM-DIMETHYLCARBAMATE;DIMETHYLAMMONIUM N,N-DIMETHYLCARBAMATE;Carbamic acid, dimethyl-, compd. with N-methylmethanamine (1:1);Dimcarb, Dimethylamine carbon dioxide complex;Dimethylammonium-dimethylcarbamate, ratio carbon dioxide/dimethylamine ;Dimethylammonium-dimethylcarbamate,ratio carbon dioxide/dimethylamine
• CAS NO: 4137-10-4
• Molecular Formula: C₂H₈N*C₃H₆NO₂
• Molecular Weight: 134.18
• Product Categories: Building Blocks;Carbonyl Compounds;Carboxylic Acid Salts;Chemical Synthesis;Organic Building Blocks
• Mol File: 4137-10-4.mol

Chemical Properties

• Melting Point: °C
• Boiling Point: 60-61 °C(lit.)
• Flash Point: 150 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.05 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.83mmHg at 25°C
• Refractive Index: n20/D 1.454(lit.)
• Storage Temp.: 2-8°C
• BRN: 4531667
• CAS DataBase Reference: DIMCARB(CAS DataBase Reference)
• NIST Chemistry Reference: DIMCARB(4137-10-4)
• EPA Substance Registry System: DIMCARB(4137-10-4)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: 2733
• WGK Germany: 3
• F: 4.4
• Hazardous Substances Data: 4137-10-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
DIMCARB is used as a solvent for the synthesis of calixarene-based ketocyanine fluorophores, which are important for various applications in the field of chemistry and materials science.
Used in Plant Material Extraction:
DIMCARB is used as a distillation extraction solvent for tannins from plant materials. This application takes advantage of its solvent properties to efficiently extract valuable compounds from natural sources.
Used in Electrodeposition:
DIMCARB is utilized in the electrodeposition of silver or lead on glassy carbon and mercury film electrodes. Its ionic liquid properties make it suitable for this purpose, enhancing the process and improving the quality of the deposited metals.
Used in Nanostructure Synthesis:
DIMCARB is employed in the synthesis of silver (Ag) and gold (Au) nanostructures, which have a wide range of applications in fields such as electronics, medicine, and catalysis.
Used as a Reusable Reaction Medium:
DIMCARB serves as a reusable reaction medium for the synthesis of monoarylidene cyclopentanones, which are valuable intermediates in the production of various organic compounds.

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

Upstream product

• 7260-94-8 N,N-dimethylcarbamic acid 
• 124-38-9 carbon dioxide 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 

Downstream Products

• 7541-16-4 methyl N,N-dimethylcarbamate 
• 17709-95-4 N,N-dimethyl-2-phenylethanethioamide 
• 121611-15-2 N,N-Dimethyl-2-pyridin-3-yl-thioacetamide 
• 15482-60-7 N,N-dimethylthiobenzamide 
• 121611-16-3 2-(2,5-Dimethyl-thiophen-3-yl)-N,N-dimethyl-thioacetamide 
• 32115-55-2 N,N-Dimethylcarbamidsaeure-trimethylsilylester 
• 7260-94-8 N,N-dimethylcarbamic acid 
• 114365-85-4 4-(Dimethylamino)-6-phenyl-2H-1,3,5-oxadiazin-2-thion 
• 114365-86-5 4-Dimethylamino-6-phenyl-[1,3,5]thiadiazin-2-one 
• 114365-84-3 4-Dimethylamino-6-phenyl-1,3-oxazin-2-thion 
• 104223-74-7 (Z)-3-Chloro-3-dimethylamino-1-phenyl-propenone 
• 76579-51-6 2-(4-chlorophenyl)-N,N-dimethylethanethioamide 
• 124-38-9 carbon dioxide 
• 124-40-3 dimethyl amine 

Relevant articles and documents

Direct NHC-catalysed redox amidation using CO2 for traceless masking of amine nucleophiles

The N-heterocyclic carbene (NHC)-catalysed redox amidation reaction is poorly developed and usually requires catalytic co-additives for electron-rich amine nucleophiles. We report a masking strategy (using CO2) that couples release of the free amine nucleophile to catalytic turnover, and in doing so, enables direct catalytic redox amidation of electron-rich amines.

Synthesis of the perdeuterated cellulose solvents N-methylmorpholine N-oxide (NMMO-d11) and N,N-dimethylacetamide (DMAC-d9)

The synthesis of the perdeuterated cellulose solvents NMMO-d11 (9) and N,N-dimethylacetamide-d9 (14) is described. NMMO-d 11 was obtained according to a five-step approach from non-labeled diglycolic acid (1) via diethylene glycole-d8 (4) and its bis-tosylate (5), which underwent cyclization with benzylamine to N-benzylmorpholine (6). The removal of the benzyl protecting group, methylation and N-oxidation completed the synthesis. DMAc-d9 (14) was obtained from deuterated acetic acid (10) and dimethylamine-carbon dioxide complex (17) with acidic alumina as the catalyst according to a solvent-free gas-solid reaction. Copyright

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

Dimethylammonium Dimethylcarbamate - A Useful Reagent for the Willgerodt-Kindler Reaction

Dimethylammonium dimethylcarbamate (dimcarb), easily accessible from dimethylamine and carbon dioxide, is a useful reagent for the Willgerodt-Kindler synthesis of N,N-dimethylthiocarboxamides.Moreover, dimcarb displays some unusual properties, and generally behaves as a preparatively useful dimethylamine source.

INVESTIGATION OF THE SALTS FORMED AS A RESULT OF THE REACTION OF HETEROCUMULENES CO2, COS, AND CS2 WITH SECONDARY AMINES BY 13C AND 1H NMR

The properties of the salts formed as a result of the reactions of carbon dioxide, carbon sulfoxide and carbon disulfide with dimethyl-, diethyl-, dipropyl-, ethylcyclohexyl-, and dicyclohexylamines, morpholine, piperidine, and hexamethyleneimine were investigated by 13C and 1H NMR methods.The free energies of activation were obtained for restricted rotation about the N-COS bond in the thiocarbamate ions of the alkylammonium thiocarbamates and also for the formation and decomposition of the carbamate ions of the alkylammonium carbamates.

TRIMETHYLSILYLATED N-ALKYL-SUBSTITUTED CARBAMATES. I. PREPARATION AND SOME REACTIONS

Trimethylsilyl N-monoalkyl- and N,N-dialkyl-carbamates have been made in 85-95percent yields by silylation of the corresponding ammonium carbamates with trimethylchlorosilane.Trimethylsilyl N,N-dimethylcarbamate can be used for silylation of alcohols, phenols, and carboxylic acids.The silylcarbamates react with carboxylic acid halides to give the corresponding acid amides.The reaction of trimethylsilyl carbamates with carboxylic anhydrides give the corresponding silyl carboxylate and acid amide, while the reaction with dicarboxylic anhydrides give the trimethylsilyl monoamide of the corresponding dicarboxylic acid, i.e.Me3SiO2CCONR1R2.