32115-55-2

Basic information

• Product Name: TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE
• Synonyms: DMCTMS;TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE;N,N-Dimethyl-(trimethylsilyl)-carbamate;N,N-Dimethyl(tri-methylsilyl)-carbamate;TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE, 98 %;Dimethylcarbamic acid trimethylsilyl ester
• CAS NO: 32115-55-2
• Molecular Formula: C₆H₁₅NO₂Si
• Molecular Weight: 161.27
• Mol File: 32115-55-2.mol

Chemical Properties

• Boiling Point: 74-75 °C20 mm Hg(lit.)
• Flash Point: 55 °F
• Appearance: /
• Density: 0.925 g/mL at 25 °C(lit.)
• Vapor Pressure: 11.7mmHg at 25°C
• Refractive Index: n20/D 1.418(lit.)
• PKA: -1.55±0.70(Predicted)
• CAS DataBase Reference: TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE(32115-55-2)
• EPA Substance Registry System: TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE(32115-55-2)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 32115-55-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE is used as a protecting group for amines and alcohols to prevent unwanted reactions or side reactions during the synthesis process. It allows chemists to carry out specific reactions without affecting the protected functional groups, ensuring the desired product is obtained.
Used in the Creation of Stable Derivatives:
TRIMETHYLSILYL N,N-DIMETHYLCARBAMATE is used to create stable derivatives for various chemical reactions. By protecting reactive sites on a molecule, it enables the synthesis of complex organic compounds with multiple functional groups, facilitating the development of new drugs, materials, and other chemical products.

InChI:InChI=1/C6H15NO2Si/c1-7(2)6(8)9-10(3,4)5/h1-5H3

Upstream product

• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 124-38-9 carbon dioxide 
• 75-77-4 chloro-trimethyl-silane 
• 4137-10-4 DIMCARB 

Downstream Products

• 1825-62-3 ethyl trimethylsilyl ether 
• 18132-93-9 heptanol trimethylsilyl ether 
• 18402-10-3 decyloxytrimethylsilane 
• 73430-27-0 (E)-N,N-dimethyl-2-nitroethenamine 
• 2754-27-0 trimethylsilyl acetate 
• 611-74-5 N,N-dimethylbenzamide 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 
• 17902-31-7 (3-methylphenoxy)trimethylsilane 
• 127-19-5 N,N-dimethyl acetamide 
• 2117-24-0 1,4-bis(trimethylsilyloxy)benzene 
• 14417-01-7 N,N-dimethylbenzenesulfonamide 
• 2078-12-8 trimethylsilyl benzoate 
• 13871-89-1 trimethylsilyl cyclohexyl ether 
• 4520-29-0 1,3-bis(trimethylsiloxy)benzene 

Relevant articles and documents

Palladium catalysed aryl amination reactions in supercritical carbon dioxide

Palladium catalysed C-N bond formation in supercritical carbon dioxide has been accomplished. Carbamic acid formation is avoided in part through the use of an N-silylamine as the coupling partner. Employing a catalyst system of Pd 2dba3 (1 mol%) and 2-dicyclohexylphosphino-2′, 4′,6′-triisopropyl-1,1′-biphenyl (X-Phos) (2 mol%) enabled the catalytic amination of aryl bromides and chlorides with N-silylanilines to be realised in excellent yield. Extension of the methodology to the N-arylation of N-silyldiarylamines, N-silylazoles and N-silylsulfonamides is reported. The Royal Society of Chemistry 2005.

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

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.