4128-37-4

Basic information

• Product Name: 1,3-diisopropylurea
• Synonyms: 1,3-diisopropylurea;N,N'-diisopropylurea;Diptocarpamidine;N,N'-Bis(1-methylethyl)urea;1,3-di(propan-2-yl)urea;NSC 112719;Urea, 1,3-diisopropyl-;Urea, 1,3-diisopropyl- (8CI)
• CAS NO: 4128-37-4
• Molecular Formula: C₇H₁₆N₂O
• Molecular Weight: 144.21474
• EINECS: 223-940-5
• Mol File: 4128-37-4.mol

Chemical Properties

• Melting Point: 185-190℃
• Boiling Point: 265℃
• Flash Point: 113℃
• Appearance: /
• Density: 0.903
• Vapor Pressure: 0.0092mmHg at 25°C
• Refractive Index: 1.434
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.05±0.46(Predicted)
• CAS DataBase Reference: 1,3-diisopropylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-diisopropylurea(4128-37-4)
• EPA Substance Registry System: 1,3-diisopropylurea(4128-37-4)

Safety Data

• Hazardous Substances Data: 4128-37-4(Hazardous Substances Data)

Usage

Uses

1. Used in Environmental Applications:
1,3-Diisopropylurea is used as a degradation product for the herbicide Bromacil, which is important for understanding the environmental impact and breakdown of this specific herbicide. This knowledge can contribute to the development of safer and more environmentally friendly herbicides in the future.
2. Used in Chemical Research:
1,3-Diisopropylurea can be utilized as a subject of study in chemical research, particularly in the fields of organic chemistry and environmental chemistry. Its properties and behavior can be investigated to gain insights into the photocatalytic degradation process and the formation of degradation products.
3. Used in Analytical Chemistry:
As a degradation product of Bromacil, 1,3-Diisopropylurea can be used as a reference compound in analytical chemistry for the development and validation of methods to detect and quantify the presence of this compound in environmental samples. This can help in monitoring the effectiveness of remediation efforts and assessing the environmental fate of the herbicide.
4. Used in Pharmaceutical Applications:
While not explicitly mentioned in the provided materials, 1,3-Diisopropylurea could potentially be investigated for its pharmaceutical applications, given its urea-based structure. Urea and its derivatives have been known to have various biological activities, and further research could explore the potential uses of 1,3-Diisopropylurea in the development of new drugs or therapeutic agents.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 2132, 1978 DOI: 10.1021/jo00405a010

InChI:InChI=1/C7H16N2O/c1-5(2)8-7(10)9-6(3)4/h5-6H,1-4H3,(H2,8,9,10)

Upstream product

• 6552-43-8 N-bromo-isobutyramide 
• 113984-39-7 1,3-Diisopropyl-2-pent-3-ynyl-isourea 
• 861327-46-0 N-chloro-isobutyramide 
• 75-44-5 phosgene 
• 75-31-0 isopropylamine 
• 67-64-1 acetone 
• 57-13-6 urea 
• 1795-48-8 Isopropyl isocyanate 
• 124-38-9 carbon dioxide 
• 108-91-8 cyclohexylamine 
• 201230-82-2 carbon monoxide 
• 75-29-6 isopropyl chloride 
• 506-77-4 cyanogen chloride 
• 590-28-3 potassium cyanate 

Downstream Products

• 75-31-0 isopropylamine 
• 5673-38-1 N-(isopropylcarbamoyl)-4-methylbenzenesulfonamide 
• 598-45-8 i-propyl isocyanide 
• 29119-58-2 Isopropylisocyanid-dichlorid 
• 693-13-0 diisopropyl-carbodiimide 
• 791-28-6 Triphenylphosphine oxide 
• 98-82-8 Isopropylbenzene 
• 691-60-1 N-isopropylurea 
• 66504-18-5 N-isopropyl-1-phenyl-1,2-cyclopropanedicarboximide 

Relevant articles and documents

Application of 15N Spectroscopy and Dynamic NMR to the Study of Ureas, Thioureas and their Lewis Acid Adducts

Rotational barriers and 15N chemical shifts have been measured in a number of ureas and thioureas.As anticipated on the basis of the 15N shifts, several previosly unobserved rotational barriers could be detected by using lanthanide reatgents or a high field spectometer.Nearly constant effects on both the rotational activation energy and the 15N shift are produced on going from ureas to the corresponding thioureas, and correlations are found between the ΔG(ex. cit) and ?15N values.The results are discussed in terms of lone pair delocalization, and anomalies with respect to general behaviour are tentatively explained in the light of the effect of steric torsion in crowded structures on the 15N shifts and rotation barriers.

Generation of Hydrogen Cyanide from the Reaction of Oxyma (Ethyl Cyano(hydroxyimino)acetate) and DIC (Diisopropylcarbodiimide)

Evolution of hydrogen cyanide (HCN) during amino acid activation using the reagent combination ethyl cyano(hydroxyimino)acetate (Oxyma)/diisopropylcarbodiimide (DIC) is observed under ambient conditions (20 °C) in N,N-dimethylformamide (DMF). Concentration versus time profiles obtained by 1H NMR spectroscopy in the presence and absence of amino acids indicate that HCN is formed upon addition of DIC to the reaction mixture and that HCN evolution continues to occur even after amino acid activation is complete when Oxyma and DIC are used in excess amounts relative to the amino acid. A mechanism for the reaction between Oxyma and DIC is proposed, and evidence for its validity was gathered by NMR spectroscopy.

Not the Alkoxycarbonylamino-acid O-Acylisourea

The reaction of equivalent amounts of N-benzyloxycarbonyl-L-valine and N,N'-di-isopropylcarbodi-imide in deuteriochloroform gives an equimolar mixture of the symmetrical anhydride of the N-protected amino-acid, N,N'-di-isopropylurea, and unchanged carbodi-imide and not the O-acylisourea adduct as reported in the literature.

Synthesis, structure, electronic and vibrational spectra of 9-(Diethylamino)-benzo(a)phenoxazin-7-ium-5-N-methacrylamide

The electronic and vibrational spectra of 9-(Diethylamino)-benzo(a)phenoxazin-7-ium-5-N-methacrylamide (Nile Blue-5-N-methacrylamide) are measured, and the results are compared with the theoretical values obtained by quantum chemical calculations. The geometry, electronic transitions, charge distribution, and the IR normal modes of this new dye and of its precursor Nile Blue have been computed by using Density Functional Theory (DFT) method with the functional B3LYP and the 6-31G(d) Gaussian basis set. The molecular properties of the two dyes, predicted and observed, are very similar in the electronic ground state. In the excited state, however, the longer lifetime and larger fluorescence quantum yield of the Nile Blue-5-methacrylamide is ascribed to an inhibition of the twisted intramolecular charge transfer (TICT) process, when the NH2 is substituted by the methacrylamide in the 5-position of the aromatic extended ring of the dye. The change in charge density of the N atom in 5-position, as well as the difference in dipole moment and ionization potential of the two dyes molecules, explain the attenuation of TICT process. The vibration spectra of both dyes are simulated properly by using the DFT method.

Reciprocal Coupling in Chemically Fueled Assembly: A Reaction Cycle Regulates Self-Assembly and Vice Versa

In biology, self-assembly of proteins and energy-consuming reaction cycles are intricately coupled. For example, tubulin is activated and deactivated for assembly by a guanosine triphosphate (GTP)-driven reaction cycle, and the emerging microtubules catalyze this reaction cycle by changing the microenvironment of the activated tubulin. Recently, synthetic analogs of chemically fueled assemblies have emerged, but examples in which assembly and reaction cycles are reciprocally coupled remain rare. In this work, we report a peptide that can be activated and deactivated for self-assembly. The emerging assemblies change the microenvironment of their building blocks, which consequently accelerate the rates of building block deactivation and reactivation. We quantitatively understand the mechanisms at play, and we are thus able to tune the catalysis by molecular design of the peptide precursor.

Co-N-doped carbon nanotubes supported on diatomite for highly efficient catalysis oxidative carbonylation of amines with CO and air

Cobalt-nitrogen-doped carbon nanotubes stably supported on diatomite were obtained by employing Co(OAc)2/phenanthroline. The resulting material was found to be excellent catalysts for the carbonylation of a variety of amines with CO other than phosgene. Both high activity and selectivity were achieved in this carbonylation process, and it allows air as a cheap oxidizing agent. Moreover the catalyst could be recycled for several times with relatively higher activity compared to homogeneous catalyst palladium acetate.

Synthesis and SAR studies of potent H+/K+-ATPase and anti-inflammatory activities of symmetrical and unsymmetrical urea analogues

A sequence of symmetrical and unsymmetrical urea derivatives 1–24 were synthesized and characterized by standard spectroscopic techniques. The synthesized analogues were tested for their in vitro H+/K+-ATPase and anti-inflammatory activities. The majority of the compounds showed outstanding activity, compared to that of omeprazole and indomethacin, usual standard drugs of antiulcer and anti-inflammatory, respectively. In particular, hydroxy, methyl, and methoxy derivatives 13–24 were the most active compounds possessing a significant amplify for diverse substituents on the benzene ring thus, contributing positively to gastric ulcer inhibition. Compounds 1–3 and 22–24 showed excellent anti-inflammatory activity due to the presence of electron-withdrawing groups (Cl and F) on the molecule.

Polynuclear Gold [AuI]4, [AuI]8, and Bimetallic [AuI4AgI] Complexes: C?H Functionalization of Carbonyl Compounds and Homogeneous Carbonylation of Amines

The synthesis of tetranuclear gold complexes, a structurally unprecedented octanuclear complex with a planar [AuI8] core, and pentanuclear [AuI4MI] (M=Cu, Ag) complexes is presented. The linear [AuI4] complex undergoes C?H functionalization of carbonyl compounds under mild reaction conditions. In addition, [AuI4AgI] catalyzes the carbonylation of primary amines to form ureas under homogeneous conditions with efficiencies higher than those achieved by gold nanoparticles.

An unexpected reaction to methodology: An unprecedented approach to transamidation

This report describes an unprecedented protocol for the synthesis of N,N′-substituted ureas using a cross-coupling method. Mono substituted ureas were modified by an economically viable and simple method using commercially available isocyanates and sodium hydride as the reagents. In addition, the method involves no expensive metal complexes or catalysts and all reactions are carried out at room temperature. Furthermore, both symmetrical and asymmetrical ureas were successfully obtained in single step reactions with reasonable yields.

Synthesis of Amides and Phthalimides via a Palladium Catalyzed Aminocarbonylation of Aryl Halides with Formic Acid and Carbodiimides

A novel method for the preparation of amides and phthalimides has been developed. The process involves a palladium catalyzed aminocarbonylation of an aryl halide, using a carbodiimide and formic acid as the carbonyl source. Experimental data suggest that the mechanistic pathway for this process involves in-situ generation of carbon monoxide from the reaction of formic acid with a carbodiimide in the presence of a palladium catalyst. The method can be used to produce a variety of amides and N-substituted phthalimides efficiently.