592-31-4

Usage

Uses

Used in Agriculture:
N-Butylurea is used as a fertilizer for rice, enhancing the growth and yield of the crop. Its application in agriculture is aimed at improving the nutritional value and productivity of rice plants.
Used in Pharmaceutical Industry:
N-Butylurea is also utilized in the preparation of drugs that are recommended for diabetes management. Its role in the pharmaceutical industry is to contribute to the development of medications that help regulate blood sugar levels and support the overall health of individuals with diabetes.

Air & Water Reactions

Water soluble.

Reactivity Profile

N-Butylurea is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). N-Butylurea decomposes on heating.

Health Hazard

ACUTE/CHRONIC HAZARDS: N-Butylurea emits toxic fumes when heated to decomposition.

Fire Hazard

Flash point data for N-Butylurea are not available. N-Butylurea is probably combustible.

Safety Profile

Moderately toxic by parenteral route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise the urea from pKEst EtOH/water, then dry it under vacuum at room temperature. [Beilstein 4 I 371, 4 IV 578.]

InChI:InChI=1/C5H12N2O/c1-2-3-4-7-5(6)8/h2-4H2,1H3,(H3,6,7,8)

Upstream product

• 590-28-3 potassium cyanate 
• 3858-78-4 n-butylamine hydrochloride 
• 60-29-7 diethyl ether 
• 4370-12-1 1-cyanoformamide 
• 109-73-9 N-butylamine 
• 684-93-5 1-methyl-1-nitrosourea 
• 556-89-8 nitrourea 
• 13464-19-2 phenyl chlorothioformate 
• 57-13-6 urea 
• 111-36-4 n-butyl isocyanide 
• 35580-87-1 2-hydroxyphenyl carbamate 
• 98493-73-3 {(C₆H₄O₂)B}2NCONH-t-C₄H₉ 
• 71-36-3 butan-1-ol 
• 64-77-7 N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide 

Downstream Products

• 6298-26-6 N-butyl-N'-furfuryl-urea 
• 28289-95-4 3-n-butyluracil 
• 92033-16-4 N-butyl-N'-p-toluoyl-urea 
• 869-01-2 1-butyl-1-nitrosourea 
• 3576-28-1 N-(butylcarbamoyl)benzamide 
• 85208-45-3 N-butyl-N'-(4-nitro-benzoyl)-urea 
• 94820-42-5 3-n-butyl-5-carbethoxyuracil 
• 92018-83-2 N-Butyl-N'-<α-chlor-phenylacetyl>-harnstoff 
• 100372-76-7 3-butyl-5-phenyl-1,3-oxazolidine-2,4-dione 
• 96364-33-9 1-Butyl-3-diphenylacetyl-harnstoff 
• 92293-72-6 1-Butyl-3-<4-acetoxy-benzoyl>-harnstoff 
• 97498-90-3 1-Butyl-3-<4-ethoxycarbonylamino-benzoyl>-harnstoff 
• 93142-71-3 1-Butyl-3-(β-phenyl-isovaleryl)-harnstoff 
• 92375-21-8 1-Butyl-3-p-toluolsulfonylacetyl-harnstoff 

Relevant academic research and scientific papers

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

An efficient one-pot synthesis of industrially valuable primary organic carbamates and: N -substituted ureas by a reusable Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] using urea as a sustainable carbonylation source

An efficient synthesis of primary carbamates and N-substituted ureas is explored with a newly developed heterogeneous polymer supported iron catalyst in the presence of a sustainable carbonylation source. The Merrifield anchored iron(ii)-anthra catalyst [FeII(Anthra-Merf)] was synthesized by functionalization of Merrifield polymer followed by grafting of iron metal. The catalyst [FeII(Anthra-Merf)] was characterized by several techniques, like SEM, EDAX, TGA, PXRD, XPS, FTIR, CHN, AAS and UV-Vis analysis. The designed polymer embedded [FeII(Anthra-Merf)] complex is a remarkably successful catalyst for the synthesis of primary organic carbamates and N-substituted ureas by using safe carbonylation agent urea with different derivatives of alcohols and amines, respectively. The reported catalyst is a potential candidate towards contributing a satisfactory yield of isolated products under suitable reaction conditions. The catalyst is recyclable and almost non-leaching in nature after six runs with an insignificant drop in catalytic activity. Thus we found an economical and viable catalyst [FeII(Anthra-Merf)] for primary carbamates and N-substituted urea synthesis under moderate reaction conditions.

A Straightforward Synthesis of N-Substituted Ureas from Primary Amides

A direct and convenient method for the preparation of N-substituted ureas is achieved by treating primary amides with phenyliodine diacetate (PIDA) in the presence of an ammonia source (NH 3 or ammonium carbamate) in MeOH. The use of 2,2,2-trifluoroethanol (TFE) as the solvent increases the electrophilicity of the hypervalent iodine species and allows the synthesis of electron-poor carboxamides. This transformation involves a nucleophilic addition of ammonia on the isocyanate intermediate generated in situ by a Hofmann rearrangement of the starting amide.

Superparamagnetic Fe3O4 Nanoparticles in a Deep Eutectic Solvent: An Efficient and Recyclable Catalytic System for the Synthesis of Primary Carbamates and Monosubstituted Ureas

Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N-disubstituted ureas. This efficient phosgene-free process used urea as an eco-friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.

A practically simple, catalyst free and scalable synthesis of: N -substituted ureas in water

A practically simple, mild and efficient method is developed for the synthesis of N-substituted ureas by nucleophilic addition of amines to potassium isocyanate in water without organic co-solvent. Using this methodology, a variety of N-substituted ureas (mono-, di- and cyclic-) were synthesized in good to excellent yields with high chemical purity by applying simple filtration or routine extraction procedures avoiding silica gel purification. The developed methodology was also found to be suitable for gram scale synthesis of molecules having commercial application in large volumes. The identified reaction conditions were found to promote a unique substrate selectivity from a mixture of two amines.

XANTHINE DERIVATIVE INHIBITORS OF BET PROTEINS

This invention relates to xanthine derivative compounds that are inhibitors of BET bromodomains proteins, the method of preparation thereof and applications thereof.

Exploring Selective Inhibition of the First Bromodomain of the Human Bromodomain and Extra-terminal Domain (BET) Proteins

A midthroughput screening follow-up program targeting the first bromodomain of the human BRD4 protein, BRD4(BD1), identified an acetylated-mimic xanthine derivative inhibitor. This compound binds with an affinity in the low micromolar range yet exerts suitable unexpected selectivity in vitro against the other members of the bromodomain and extra-terminal domain (BET) family. A structure-based program pinpointed a role of the ZA loop, paving the way for the development of potent and selective BET-BRDi probes.

4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas

A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.

Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid

A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquid 1,1,3,3-tetramethylguanidine lactate [TMG][Lac] is described. The ureas were synthesized from amines and potassium cyanate, which on reaction with cyanoacetic acid in the presence of acetic anhydride in the same pot afforded cyanoacetylureas, which undergo cyclization in [TMG][Lac] as solvent as well as catalyst to afford 6-aminouracils. One-pot synthesis of cyanoacetylureas, efficient and rapid cyclization, better yield, shorter reaction time, easy workup procedure, and recyclability of the ionic liquid are some advantages of this procedure.

An improved method for the preparation of alkyl/arylurea derivatives using chlorocarbonylsulfenyl chloride as carbonylating agent

A convenient procedure has been developed for preparation of aminesubstituted or monomethylamine-substituted alkyl/arylurea derivatives. The method comprises two steps-reaction of an alkyl/aryl amine with chlorocarbonylsulfenyl chloride in a non-polar solvent to produce an alkyl/arylcarbonylsulfenyl chloride, then reaction of this alkyl/ arylcarbonylsulfenyl chloride with ammonia or monomethylamine in a two-phase reaction with a phase-transfer catalyst, to produce the corresponding alkyl/aryl-substituted urea. Springer Science+Business Media B.V. 2012.