623-95-0

Basic information

• Product Name: N,N'-Dipropylurea
• Synonyms: 1,3-DIPROPYLUREA;N,N'-DIPROPYLUREA;1,3-Di-n-propylurea;N,N'-Di-n-propylurea
• CAS NO: 623-95-0
• Molecular Formula: C₇H₁₆N₂O
• Molecular Weight: 144.21
• EINECS: 210-821-8
• Product Categories: Small molecule;Carbonyl Compounds;Organic Building Blocks;Ureas;Aliphatics;Amines;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 623-95-0.mol

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 262.84°C (rough estimate)
• Flash Point: 122.3 °C
• Appearance: /
• Density: 1.0176 (rough estimate)
• Refractive Index: 1.4331 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.43±0.46(Predicted)
• BRN: 1751900
• CAS DataBase Reference: N,N'-Dipropylurea(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Dipropylurea(623-95-0)
• EPA Substance Registry System: N,N'-Dipropylurea(623-95-0)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 3
• Hazardous Substances Data: 623-95-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Dipropylurea is used as an intermediate for the synthesis of symmetrically N,N'-disubstituted aliphatic ureas, which are vital in the development of antitumor drugs. Its role in the creation of these compounds contributes to the fight against cancer and the advancement of cancer treatment options.
Used in Research and Development:
Labelled N,N'-Dipropylurea (D492460) is utilized in the synthesis of symmetrically N,N'-disubstituted aliphatic ureas, which are essential for the development of antitumor drugs. This labelled compound aids researchers in understanding the mechanisms of action and the effectiveness of these drugs in combating cancer cells.

Upstream product

• 107-10-8 propylamine 
• 15719-64-9 methylammonium carbonate 
• 110-78-1 Propyl isocyanate 
• 821-79-4 N,N'-dipropylcarbodiimide 
• 628-30-8 n-Propyl isothiocyanate 
• 64221-20-1 Propyl-thiocarbamic acid; compound with propylamine 
• 556-53-6 N-propylamine hydrochloride 
• 57-13-6 urea 
• 96-49-1 [1,3]-dioxolan-2-one 
• 201230-82-2 carbon monoxide 
• 108-32-7 1,2-propylene cyclic carbonate 
• 124-38-9 carbon dioxide 
• 162976-69-4 1H-benzimidazol-2-ylcarbamic acid methyl ester 
• 6268-43-5 1,3-di-pyridin-2-yl-urea 

Downstream Products

• 107-10-8 propylamine 
• 24570-88-5 4-methyl-N-( propylcarbamoyl)benzenesulfonamide 
• 41862-14-0 6-amino-1,3-dipropyluracil 
• 340021-17-2 3-(4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)bicyclo[2.2.2]octan-1-yl)propanoic acid 
• 21036-96-4 Dipropylparabansaeure 
• 67-56-1 methanol 
• 1242143-89-0 5-(1,3-dioxo-1,3-diphenylpropan-2-yl)-5-phenyl-1,3-dipropylimidazolidine-2,4-dione 
• 81250-33-1 1,3-di-n-propyl-5-nitroso-6-aminouracil 
• 31542-62-8 1,3-dipropylxanthine 
• 866917-63-7 3-methyl-1-(4-nitro-phenyl)-5,7-dipropyl-1H,7H-1,2,3a,5,7,8-hexaaza-cyclopenta[a]indene-4,6-dione 
• 866917-64-8 1-(4-amino-phenyl)-3-methyl-5,7-dipropyl-1H,7H-1,2,3a,5,7,8-hexaaza-cyclopenta[a]indene-4,6-dione 

Relevant articles and documents

Development and Application of Subtype-Selective Fluorescent Antagonists for the Study of the Human Adenosine A1Receptor in Living Cells

The adenosine A1 receptor (A1AR) is a G-protein-coupled receptor (GPCR) that provides important therapeutic opportunities for a number of conditions including congestive heart failure, tachycardia, and neuropathic pain. The development of A1AR-selective fluorescent ligands will enhance our understanding of the subcellular mechanisms underlying A1AR pharmacology facilitating the development of more efficacious and selective therapies. Herein, we report the design, synthesis, and application of a novel series of A1AR-selective fluorescent probes based on 8-functionalized bicyclo[2.2.2]octylxanthine and 3-functionalized 8-(adamant-1-yl) xanthine scaffolds. These fluorescent conjugates allowed quantification of kinetic and equilibrium ligand binding parameters using NanoBRET and visualization of specific receptor distribution patterns in living cells by confocal imaging and total internal reflection fluorescence (TIRF) microscopy. As such, the novel A1AR-selective fluorescent antagonists described herein can be applied in conjunction with a series of fluorescence-based techniques to foster understanding of A1AR molecular pharmacology and signaling in living cells.

Development of a Polo-like Kinase-1 Polo-Box Domain Inhibitor as a Tumor Growth Suppressor in Mice Models

Polo-like kinase-1 (Plk1) plays a key role in mitosis and has been identified as an attractive anticancer drug target. Plk1 consists of two drug-targeting sites, namely, N-terminal kinase domain (KD) and C-terminal polo-box domain (PBD). As KD-targeting inhibitors are associated with severe side effects, here we report on the pyrazole-based Plk1 PBD inhibitor, KBJK557, which showed a remarkable in vitro anticancer effect by inducing Plk1 delocalization, mitotic arrest, and apoptosis in HeLa cells. Further, in vivo optical imaging analysis and antitumorigenic activities in mouse xenograft models demonstrate that KBJK557 preferentially accumulates in cancer cells and selectively inhibits cancer cell proliferation. Pharmacokinetic profiles and partition coefficients suggest that KBJK557 was exposed in the blood and circulated through the organs with an intermediate level of clearance (t1/2, 7.73 h). The present investigation offers a strategy for specifically targeting cancer using a newly identified small-molecule inhibitor that targets the Plk1 PBD.

PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS

The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).

Well-Defined Cesium Benzotriazolide as an Active Catalyst for Generating Disubstituted Ureas from Carbon Dioxide and Amines

The reaction of alkali metal carbonates with various azole compounds produced a new series of alkali metal azolides, and they were applied as active catalysts for the production of disubstituted ureas from the carboxylation of various amines with CO2. Among them, cesium benzotriazolide (Cs[BTd]) was found to be the most active for the carboxylation reaction and was structurally characterized by single-crystal X-ray diffraction. The crystal structure of highly hygroscopic Cs[BTd] was found to be [BTA]???Cs[BTd], which explains why it is a water-tolerant active species for this carboxylation reaction, leading to a maximum turnover frequency of 344 h?1 as well as high recyclability even after five successive runs.

CeO2-catalyzed direct synthesis of dialkylureas from CO2 and amines

CeO2 showed higher activity for the direct synthesis of 1,3-dibutylurea (DBU) from CO2 and n-butylamine than the metal oxides tested. The solvent largely influenced the reaction over CeO2, and N-methylpyrrolidone (NMP) was preferable among various solvents tested from the viewpoints of activity and selectivity. The catalyst system composed of CeO2 catalyst and NMP solvent (CeO2 in NMP) was applicable to the reactions of various amines such as linear primary alkylamines or branched primary alkylamines, although tert-butylamine afforded low conversion. In contrast, secondary amines and aniline provided no yield of the ureas. The combination of 2-cyanopyridine with CeO2 in NMP (CeO2 in NMP with 2-cyanopyridine) promoted the transformation of the unreactive amines, showing that tert-butylamine and aniline were converted to the corresponding ureas in 82% and 80% yields, respectively. These yields are much higher than those reported in the previous literatures, indicating that CeO2 in NMP with 2-cyanopyridine drastically promoted transformation of amines with low reactivity.

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.

Pyrimidine-2,4,6-trione derivatives and their inhibition of mutant SOD1-dependent protein aggregation. Toward a treatment for amyotrophic lateral sclerosis

Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative disease characterized by the progressive loss of motor neurons, leading to muscle weakness, paralysis, and death, most often from respiratory failure. The only FDA-approved drug for the treatment of ALS, riluzole, only extends the median survival in patients by 2-3 months. There is an urgent need for novel therapeutic strategies for this devastating disease. Using a high-throughput screening assay targeting an ALS cultured cell model (PC12-G93A-YFP cell line), we previously identified three chemotypes that were neuroprotective. We present a further detailed analysis of one promising scaffold from that group, pyrimidine-2,4,6-triones (PYTs), characterizing a number of PYT analogues using SAR and ADME. The PYT compounds show good potency, superior ADME data, low toxicity, brain penetration, and excellent oral bioavailability. Compounds from this series show 100% efficacy in the protection assay with a good correlation in activity between the protection and protein aggregation assays. The modifications of the PYT scaffold presented here suggest that this chemical structure may be a novel drug candidate scaffold for use in clinical trials in ALS.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent

Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.

Synthesis of urea derivatives from CO2 and amines catalyzed by polyethylene glycol supported potassium hydroxide without dehydrating agents

Polyethylene glycol supported potassium hydroxide (KOH/PEG1000) was developed as a recyclable catalyst for facile synthesis of urea derivatives from amines and CO2 without utilization of additional dehydrating agents. Primary aliphatic amines, secondary aliphatic amines, and diamines can be converted into the corresponding urea derivatives in moderate yields. Furthermore, the catalyst can be recovered after a simple separation procedure, and reused over 5 times with retention of high activity. Georg Thieme Verlag Stuttgart.