591-62-8

Usage

InChI:InChI=1/C7H15NO2/c1-3-5-6-8-7(9)10-4-2/h3-6H2,1-2H3,(H,8,9)

Upstream product

• 56-23-5 tetrachloromethane 
• 857797-90-1 butyl-μ-imido-dicarbonic acid diethyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 109-73-9 N-butylamine 
• 66508-93-8 ethyl 2-(hydroxyimino)-3-oxybutyrate 
• 590-28-3 potassium cyanate 
• 64-17-5 ethanol 
• 109-69-3 n-Butyl chloride 
• 201230-82-2 carbon monoxide 
• 515-84-4 Ethyl trichloroacetate 
• 32315-93-8 ethyl (2-hydroxyphenyl) carbonate 
• 3278-35-1 S-(ethoxycarbonyl) O-ethyl dithiocarbonate 
• 74-88-4 methyl iodide 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 6558-78-7 ethyl N-butyl-N-nitrosocarbamate 
• 846-74-2 1,3,5-tributyl-[1,3,5]triazinane-2,4,6-trione 
• 111-36-4 n-butyl isocyanide 
• 31844-65-2 N-Butyl-N-methylbenzenemethanamine 
• 110-68-9 N-n-butyl-N-methylamine 

Relevant academic research and scientific papers

N-Substituted carbamate synthesis using urea as carbonyl source over TiO2-Cr2O3/SiO2 catalyst

The use of urea as an active form of carbon dioxide is a feasible way to substitute phosgene in the chemical industry. This paper reports an effective route for the synthesis of N-substituted carbamates from amines, urea and alcohols. Under the optimized reaction conditions, several important N-substituted carbamates were successfully synthesized in 95-98% yields over a TiO2-Cr2O3/SiO2 catalyst. The catalyst could be reused for several runs without deactivation. The catalysts were characterized by BET, XPS, XRD, and TPD, which suggested that the strength and amount of the acidic and basic sites might be the major reason for the high catalytic activity of TiO2-Cr2O3/SiO2.

Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.

Structure-activity relationships of a small-molecule inhibitor of the PDZ domain of PICK1

Recently, we described the first small-molecule inhibitor, (E)-ethyl 2-cyano-3-(3,4-dichlorophenyl)acryloylcarbamate (1), of the PDZ domain of protein interacting with Cα-kinase 1 (PICK1), a potential drug target against brain ischemia, pain and cocaine addiction. Herein, we explore structure-activity relationships of 1 by introducing subtle modifications of the acryloylcarbamate scaffold and variations of the substituents on this scaffold. The configuration around the double bond of 1 and analogues was settled by a combination of X-ray crystallography, NMR and density functional theory calculations. Thereby, docking studies were used to correlate biological affinities with structural considerations for ligand-protein interactions. The most potent analogue obtained in this study showed an improvement in affinity compared to 1 and is currently a lead in further studies of PICK1 inhibition.

Cyclic guanidine organic catalysts: What is magic about triazabicyclodecene?

(Chemical Equation Presented) The bicyclic guanidine 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.

Catalytic activity of MCM-41-TBD in the selective preparation of carbamates and unsymmetrical alkyl carbonates from diethyl carbonate

The synthesis of carbamates 3 and unsymmetrical alkyl carbonates 5 by reaction of diethyl carbonate with aliphatic amines or alcohols has been realized by using as heterogeneous catalyst a hybrid organic-inorganic material prepared by anchoring TBD to MCM-41 silica. Products are obtained in high yield and very good selectivity and the solid catalyst can be recovered simply by filtration and reused for different cycles without apparent lowering of activity. A supported N -carbethoxyguanidinium active intermediate is proposed, and some spectroscopic data are shown to support the mechanistic hypothesis.

A novel PdCl2/ZrO2-SO42- catalyst for synthesis of carbamates by oxidative carbonylation of amines

At 170°C and ca. 4.0 MPa, oxidative carbonylation of aromatic amines to synthesize corresponding carbamates over a novel PdCl2/ZrO2-SO42- catalyst could proceed with high conversion and selectivity.

A simple method for the synthesis of carbamates

A new method for carbamate synthesis using aryl and alkylamines with sodium hydride and diethylcarbonate in dry benzene is described.

Processes for producing carbamates and isocyanates

Processes for producing carbamates comprise contacting a first reactant selected from primary amine components, secondary amine components, urea components and mixtures thereof; carbon monoxide; at least one organic hydroxyl component and at least one oxygen-containing oxidizing agent in the presence of a catalyst composition comprising at least one metal macrocyclic complex, preferably in the further presence of a halogen component.

Preparation of urethanes by oxidative carbonylation of amines using copper carboxylates as oxidants

A process for preparing urethanes by reacting a primary or secondary amine with carbon monoxide, an alcohol, a catalytic quantity of a compound or complex of palladium, platinum or rhodium and a stoichiometric quantity of a copper(II) salt of a monocarboxylic acid. When the amine is aromatic, the process is conducted in the presence of a selected Lewis base promoter and a compound or complex of palladium.

Chemical Ionization Mass Spectra of Urethanes

Chemical ionization mass spectra using methane as the reagent gas are reported for 33 urethanes of general structure RNHCO2C2H5 nH2n+1 (n=1-8), CH2CH=CH2, cyclo-C6H11, Ph, PhCH2, PhCH2CH2, and Ph(CH3)CH> and R2NCO2C2H5 nH2n+1 (n=1-4)>.Abundant MH+ ions are present in all the spectra, accompanied by satellite peaks corresponding to + and +.Four classes of fragment ions are of general importance in the spectra.Two of these, + and +, are associated with the CO2C2H5 group.The other two, corresponding to alkane and alkene elimination from MH+, arise from the RNH or R2N function.The mechanisms whereby these fragment ions are formed are discussed and their analytical utility is illustrated by reference to the spectra of the four isomeric C4H9NHCO2C2H5 and the eight isomeric C5H11NHCO2C2H5 compounds.The results of 2H-labelling studies are presented and a comparison is made between the methane and ammonia chemical ionisation spectra of selected urethanes.