592-31-4

Basic information

• Product Name: N-Butylurea
• Synonyms: 1-Butylurea;butyl-ure;monobutylurea;NCI-C02131;N-n-Butylurea;urea,N-butyl-;N-BUTYLUREA;BUTYLUREA
• CAS NO: 592-31-4
• Molecular Formula: C₅H₁₂N₂O
• Molecular Weight: 116.16
• EINECS: 209-748-4
• Product Categories: Carbonyl Compounds;Organic Building Blocks;Ureas
• Mol File: 592-31-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 95-98 °C(lit.)
• Boiling Point: 217.23°C (rough estimate)
• Flash Point: 62.3 °C
• Appearance: Appearance White powder;Content ≥99%;Water content ≤0,25%
• Density: 1.0551 (rough estimate)
• Vapor Pressure: 0.944mmHg at 25°C
• Refractive Index: 1.4432 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Methanol
• PKA: 14.38±0.46(Predicted)
• Water Solubility: soluble
• BRN: 1744775
• CAS DataBase Reference: N-Butylurea(CAS DataBase Reference)
• NIST Chemistry Reference: N-Butylurea(592-31-4)
• EPA Substance Registry System: N-Butylurea(592-31-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-68-37-20/21/22
• Safety Statements: 45-36/37-36
• WGK Germany: 3
• RTECS: YS3675000
• TSCA: Yes
• Hazardous Substances Data: 592-31-4(Hazardous Substances Data)

Usage

Description

N-Butylurea is an odorless white solid that exists as a white to almost white crystalline powder. It is a chemical compound with the molecular formula C5H11N. Due to its unique properties, it finds applications in various industries.

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 articles and documents

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.

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.

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.