1792-17-2

Basic information

• Product Name: Dibutylurea
• Synonyms: n,n’-dibutylurea(asimpurity);Urea, N,N'-dibutyl-;urea,1,3-dibutyl-;N,N'-DI-N-BUTYLUREA;N,N'-DIBUTYLUREA;TIMTEC-BB SBB007953;1,3-DIBUTYLUREA;DIBUTYLUREA
• CAS NO: 1792-17-2
• Molecular Formula: C₉H₂₀N₂O
• Molecular Weight: 172.27
• EINECS: 217-258-7
• Product Categories: Agro-Products, Aliphatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1792-17-2.mol
• Article Data: 92

Chemical Properties

• Melting Point: 65-75 °C
• Boiling Point: 115°C 0,03mm
• Flash Point: 115°C/0.03mm
• Appearance: white to pink or light beige crystalline powder
• Density: 0.9845 (rough estimate)
• Vapor Pressure: 0.0172mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.44±0.46(Predicted)
• BRN: 1704165
• CAS DataBase Reference: Dibutylurea(CAS DataBase Reference)
• NIST Chemistry Reference: Dibutylurea(1792-17-2)
• EPA Substance Registry System: Dibutylurea(1792-17-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 1792-17-2(Hazardous Substances Data)

Usage

Chemical Properties

white to pink or light beige crystalline powder

Uses

Different sources of media describe the Uses of 1792-17-2 differently. You can refer to the following data:
1. N,N'-Dibutylurea is a degradation product of Benomyl, the active ingredient in Benlate fungicides.
2. N,N''-Dibutylurea is a degradation product of Benomyl, the active ingredient in Benlate fungicides.

Preparation

The reactions under CO2 pressured conditions were carried out in a stainless steel reactor (SUS 304, 30 mL, TVS-5 type). Thus, butylamine (2.9 g, 40 mmol), Ph3SbO (370 mg, 1.0 mmol), P4S10 (890 mg, 2.0 mmol), and benzene (20 mL) were charged into the reactor, and then CO2 was introduced at a pressure of 4.9 MPa (50 kg cm-2, ca. 65 mmol) at room temperature. The reactor was heated at 80 ℃ in a temperature-regulated incubator for 12 h. When a reaction temperature higher than 100 ℃ was necessary, an oil bath was used. After the heating, the reactor was cooled and carefully decompressed. The contents were treated with hot benzene (3×20 mL) and filtered to remove an insoluble residue containing the catalyst and phosphoric acid derivatives. The collected benzene solution was then concentrated to dryness in vacuo with cooling. Pure 1,3-dibutylurea was isolated by recrystallization from ligroin (yield 2.99 g, 88%).

Synthesis Reference(s)

Synthetic Communications, 21, p. 1923, 1991 DOI: 10.1080/00397919108021783

InChI:InChI=1/C9H20N2O/c1-3-5-7-11(9(10)12)8-6-4-2/h3-8H2,1-2H3,(H2,10,12)

Upstream product

• 142-27-8 carbamic acid-(2-amino-ethyl ester) 
• 109-73-9 N-butylamine 
• 57-13-6 urea 
• 3858-78-4 n-butylamine hydrochloride 
• 6376-70-1 6-chloro-3,4-dihydro-2H-1,4-benzothiazinone 
• 111-36-4 n-butyl isocyanide 
• 201230-82-2 carbon monoxide 
• 110-91-8 morpholine 
• 142-84-7 di-n-propylamine 
• 62-53-3 aniline 
• 109-69-3 n-Butyl chloride 
• 75-18-3 dimethylsulfide 
• 75-05-8 acetonitrile 
• 624-92-0 Dimethyldisulphide 

Downstream Products

• 41862-16-2 6-Amino-1,3-dibutylpyrimidine-2,4(1H,3H)-dione 
• 13909-67-6 N-Butyl-N'-phenylmethansulfonyl-harnstoff 
• 339-43-5 carbutamide 
• 6630-00-8 N-[4-({[(butylamino)carbonyl]amino}sulfonyl)phenyl]acetamide 
• 13909-64-3 N-(butylcarbamoyl)-4-chlorobenzenesulfonamide 
• 13738-74-4 3-(p-nitrobenzenesulfonyl)-1-butylurea 
• 10505-92-7 4-(butylcarbamoyl-sulfamoyl)-benzoic acid ethyl ester 
• 64-77-7 N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide 
• 109-73-9 N-butylamine 
• 591-62-8 N-(ethoxycarbonyl)butylamine 
• 619-37-4 N,N-di-n-butylurea 
• 111-36-4 n-butyl isocyanide 
• 67-56-1 methanol 
• 33070-58-5 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide 

Relevant articles and documents

Penicillium expansum lipase-coated magnetic Fe3O 4-polymer hybrid hollow nanoparticles: A highly recoverable and magnetically separable catalyst for the synthesis of 1,3-dibutylurea

Herein, amino-epoxy supports were innovatively imported onto magnetic nanoparticles (Fe3O4-polymer hybrid nanospheres) for immobilizing enzymes. This new support has a coating layer with dual functional groups (epoxy and amino-epoxy). Consequently, this support has great anionic exchange power and a high number of epoxy groups. The acquired immobilized Penicillium expansum lipase in combination with this heterofunctional support represents a novel class of heterogeneous catalyst towards the synthesis of 1,3-dibutylurea from ethylene carbonate and butylamine, which has not been very commonly catalyzed by enzymes. After optimization of the reaction conditions, the yield of 1,3-dibutylurea was 77% under solvent free conditions at 60 °C. Moreover, after completion of reaction, the catalyst was simply recovered by an external conventional magnet and recycled without significant loss in the catalytic activity (up to ten cycles). the Partner Organisations 2014.

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