691-60-1

Basic information

• Product Name: ISOPROPYLUREA
• Synonyms: (1-methylethyl)-ure;(1-methylethyl)urea;1-Isopropylurea;isopropyl-ure;N-(1-methylethyl)urea;N-Isopropylurea;Urea, (1-methylethyl)-;Urea, isopropyl-
• CAS NO: 691-60-1
• Molecular Formula: C₄H₁₀N₂O
• Molecular Weight: 102.14
• EINECS: 211-722-2
• Mol File: 691-60-1.mol

Chemical Properties

• Melting Point: 154.25°C
• Boiling Point: 191.46°C (rough estimate)
• Flash Point: 44.1°C
• Appearance: /
• Density: 1.0739 (rough estimate)
• Vapor Pressure: 4.06mmHg at 25°C
• Refractive Index: 1.4386 (estimate)
• CAS DataBase Reference: ISOPROPYLUREA(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPYLUREA(691-60-1)
• EPA Substance Registry System: ISOPROPYLUREA(691-60-1)

Safety Data

• Hazardous Substances Data: 691-60-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Isopropylurea is used as a key intermediate in the synthesis of symmetrical and unsymmetrical urea analogues. These analogues exhibit H+/K+-ATPase inhibitory and anti-inflammatory activities, making them valuable for the development of new drugs targeting gastric acid-related disorders and inflammation.
Used in Chemical Synthesis:
Isopropylurea serves as a versatile building block in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its ability to participate in various chemical reactions, such as nucleophilic substitution, makes it a valuable component in the creation of complex molecular structures.
Used in Research and Development:
Isopropylurea is utilized in research and development settings to explore its potential applications and properties. Scientists and chemists use this compound to study its reactivity, stability, and interactions with other molecules, which can lead to the discovery of new chemical processes and applications.

InChI:InChI=1/C4H10N2O/c1-3(2)6-4(5)7/h3H,1-2H3,(H3,5,6,7)

Upstream product

• 17686-66-7 urethanoacetiminocarbamate 
• 67-64-1 acetone 
• 57-13-6 urea 
• 1795-48-8 Isopropyl isocyanate 
• 556-89-8 nitrourea 
• 75-31-0 isopropylamine 
• 82387-37-9 (Z)-3-(3-Isopropyl-ureido)-2-methyl-acrylic acid methyl ester 
• 82387-36-8 (E)-3-(3-Isopropyl-ureido)-2-methyl-acrylic acid methyl ester 
• 13256-32-1 1,3 dimethyl 1 nitrosourea 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 123-91-1 1,4-dioxane 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 35695-49-9 isopropylcyanamide 

Downstream Products

• 85432-35-5 5,5-diethyl-1-isopropylpyrimidinetrione 
• 69998-14-7 1-isopropylpyrimidine-2,4,6(1H,3H,5H)trione 
• 91767-02-1 N-Isopropyl-N'-<α-chlor-phenylacetyl>-harnstoff 
• 40589-66-0 3-Benzoyl-1-isopropyl-harnstoff 
• 91557-58-3 3-o-Toluoyl-1-i-propylharnstoff 
• 7248-86-4 N-Chloracetyl-N'-isopropyl-harnstoff 
• 13909-94-9 N--N'-isopropyl-harnstoff 
• 40589-67-1 N-Isopropyl-N'-phenylacetylharnstoff 
• 25818-96-6 1-isopropyl-1H-pyrimidine-2,4-dione 
• 16830-14-1 N-isopropyl-N-nitrosourea 
• 85432-36-6 5-ethyl-5-phenyl-1-isopropyl-pyrimidinetrione 
• 113885-20-4 6-amino-1-isopropylpyrimidine-2,4(1H,3H)-dione 
• 4128-37-4 1,3-diisopropylurea 
• 19895-44-4 1-phenyl-3-i-propylurea 

Relevant articles and documents

METHODS OF TREATMENT WITH MYOSIN MODULATOR

Disclosed herein are methods of treatment comprising administering a therapeutically effective amount of a myosin modulator or a pharmaceutically acceptable salt thereof to a subject in need thereof and diagnostic methods useful in connection with those treatments. Due to observations unfolding in clinical trials with mavacamten and with mavacamten and other myosin inhibitors in the pre-clinical setting, new insights into how myosin inhibitors can be used beneficially to impact the disease state of HCM and other diseases are provided herein.

Catalytic hydration of cyanamides with phosphinous acid-based ruthenium(ii) and osmium(ii) complexes: scope and mechanistic insights

The synthesis of a large variety of ureas R1R2NC(O)NH2 (R1 and R2 = alkyl, aryl or H; 26 examples) was successfully accomplished by hydration of the corresponding cyanamides R1R2NCN using the phosphinous acid-based complexes [MCl2(η6-p-cymene)(PMe2OH)] (M = Ru (1), Os (2)) as catalysts. The reactions proceeded cleanly under mild conditions (40-70 °C), in the absence of any additive, employing low metal loadings (1 molpercent) and water as the sole solvent. In almost all the cases, the osmium complex 2 featured a superior reactivity in comparison to that of its ruthenium counterpart 1. In addition, for both catalysts, the reaction rates observed for the hydration of the cyanamide substrates were remarkably faster than those involving classical aliphatic and aromatic nitriles. Computational studies allowed us to rationalize all these trends. Thus, the calculations indicated that the presence of a nitrogen atom directly linked to the CN bond depopulates electronically the nitrile carbon by inductive effect when coordinated to the metal center, thus favouring the intramolecular nucleophilic attack of the OH group of the phosphinous acid ligand to this carbon. On the other hand, the higher reactivity of Os vs. Ru seems to be related with the lower ring strain on the incipient metallacycle that starts to form in the transition state associated with this key step in the catalytic cycle. Indirect experimental evidence of the generation of the metallacyclic intermediates was obtained by studying the reactivity of [RuCl2(η6-p-cymene)(PMe2OH)] (1) towards dimethylcyanamide in methanol and ethanol. The reactions afforded compounds [RuCl(η6-p-cymene)(PMe2OR)(NCNMe2)][SbF6] (R = Me (5a), Et (5b)), resulting from the alcoholysis of the metallacycle, which could be characterized by single-crystal X-ray diffraction. This journal is

Synthesis and Structure of 1-Substituted Semithioglycolurils

Two methods for the synthesis of previously unavailable 1-substituted semithioglycolurils were developed. These methods consist of the cyclocondensation of 1-substituted ureas with 4,5-dihydroxy- or 4,5-dimethoxyimidazolidine-2-thione or glyoxal, followed by the reaction of the resulting 1-substituted 4,5-dihydroxyimidazolidine-2-ones with HSCN in a two-step one-pot procedure. Two of the desired semithioglycolurils were obtained as conglomerates.

TYK2 INHIBITORS AND USES THEREOF

Described herein are compounds that are useful in treating a TYK2-mediated disorder. In some embodiments, the TYK2-mediated disorder is an autoimmune disorder, an inflammatory disorder, a proliferative disorder, an endocrine disorder, a neurological disorder, or a disorder associated with transplantation.

Myosin inhibitor, as well as preparation method and application thereof

The invention relates to the field of medicinal chemistry, in particular to a myosin inhibitor, as well as a preparation method and application thereof. The invention provides a compound or pharmacologically acceptable salt, an isomer, a prodrug, a polymorphic substance or a solvate thereof. A chemical structural formula of the compound is as shown in a formula I. Compared with other similar medicines in the prior art, the compound or the pharmacologically acceptable salt, the isomer, the prodrug, the polymorphic substance or the solvate thereof provided by the invention have better activity and a more ideal pharmacokinetics characteristic.

A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation

We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C=O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.

Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation

A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.

MAVACAMTEN FOR USE IN THE TREATMENT OF HYPERTROPHIC CARDIOMYOPATHY

Provided are methods for treating hypertrophic cardiomyopathy and diastolic dysfunction.

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.

Synthesis and Antiangiogenic Properties of Tetrafluorophthalimido and Tetrafluorobenzamido Barbituric Acids

The development of novel thalidomide derivatives as immunomodulatory and anti-angiogenic agents has revived over the last two decades. Herein we report the design and synthesis of three chemotypes of barbituric acids derived from the thalidomide structure: phthalimido-, tetrafluorophthalimido-, and tetrafluorobenzamidobarbituric acids. The latter were obtained by a new tandem reaction, including a ring opening and a decarboxylation of the fluorine-activated phthalamic acid intermediates. Thirty compounds of the three chemotypes were evaluated for their anti-angiogenic properties in an ex vivo assay by measuring the decrease in microvessel outgrowth in rat aortic ring explants. Tetrafluorination of the phthalimide moiety in tetrafluorophthalimidobarbituric acids was essential, as all of the nonfluorinated counterparts lost anti-angiogenic activity. An opening of the five-membered ring and the accompanying increased conformational freedom, in case of the corresponding tetrafluorobenzamidobarbituric acids, was well tolerated. Their activity was retained, although their molecular structures differ in torsional flexibility and possible hydrogen-bond networking, as revealed by comparative X-ray crystallographic analyses.