54648-79-2

Basic information

• Product Name: O-METHYL-N,N'-DIISOPROPYLISOUREA
• Synonyms: O-METHYL-N,N'-DIISOPROPYLISOUREA;N,N'-DIISOPROPYL-O-METHYLISOUREA;1,3-Diisopropyl-2-methylisourea;CarbaMiMidic acid, N,N'-bis(1-Methylethyl)-, Methyl ester;methyl N,N'-di(propan-2-yl)carbamimidate
• CAS NO: 54648-79-2
• Molecular Formula: C₈H₁₈N₂O
• Molecular Weight: 158.24
• EINECS: 259-275-2
• Product Categories: Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Ureas;Reagents for Acylation;Acylation Reagents;Analytical Reagents;Analytical/Chromatography;Derivatization Reagents;Derivatization Reagents GC
• Mol File: 54648-79-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 50-52 °C10 mm Hg
• Flash Point: 96 °F
• Appearance: /
• Density: 0.872 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.436
• Storage Temp.: 2-8°C
• PKA: 9.85±0.50(Predicted)
• BRN: 1753052
• CAS DataBase Reference: O-METHYL-N,N'-DIISOPROPYLISOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: O-METHYL-N,N'-DIISOPROPYLISOUREA(54648-79-2)
• EPA Substance Registry System: O-METHYL-N,N'-DIISOPROPYLISOUREA(54648-79-2)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10-21
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 54648-79-2(Hazardous Substances Data)

Usage

Description

O-METHYL-N,N'-DIISOPROPYLISOUREA is an organic compound that serves as an important intermediate in the synthesis of various chemical products. It is characterized by its unique molecular structure, which consists of an isourea group with diisopropyl substituents and a methyl group at the ortho position.

Uses

Used in Pharmaceutical Industry:
O-METHYL-N,N'-DIISOPROPYLISOUREA is used as a synthetic intermediate for the production of proline betaine (stahydrine) and 4-hydroxyproline betaine (betoncine). These compounds have potential applications in the pharmaceutical industry, particularly in the development of drugs targeting various medical conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, O-METHYL-N,N'-DIISOPROPYLISOUREA is utilized as a key building block for the creation of more complex molecules. Its unique structure allows for further functionalization and modification, making it a valuable component in the synthesis of a wide range of chemical products.

Upstream product

• 96-35-5 glycolic acid methyl ester 
• 693-13-0 diisopropyl-carbodiimide 
• 67-56-1 methanol 

Downstream Products

• 56755-22-7 C₁₂H₁₇NO₂ 
• 128576-72-7 (2S)-4-benzyl 1-methyl N-benzylaspartate 
• 128576-71-6 (2S)-4-benzyl 1-methyl N-benzyl-N-methylaspartate 
• 4358-87-6 (RS)-methyl mandelate 
• 118650-08-1 (5-bromo-pyridin-3-yl)-acetic acid methyl ester 
• 615-22-5 2-methylmercaptobenzothiazole 
• 13673-62-6 2-methylsulfanyl-benzoxazole 
• 4128-37-4 1,3-diisopropylurea 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 113266-23-2 L,L-2-[2-(2-benzyloxycarbonylaminoacetylamino)-3-phenylpropionylamino]-3-methylbutyric acid methyl ester 
• 141215-69-2 N-(tert-butyloxycarbonyl)-2-(3-indolyl)glycin methyl ester 
• 103-26-4 Methyl cinnamate 
• 40628-41-9 methyl cyclobut-1-enecarboxylate 
• 64363-86-6 α-N,N,N-trimethyltryptophan betaine 

Relevant articles and documents

Metal-Free and Alkali-Metal-Catalyzed Synthesis of Isoureas from Alcohols and Carbodiimides

The first addition of alcohols to carbodiimides catalyzed by transition-metal-free compounds employs 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its alkali metal salts. Isoureas are obtained in short reaction times and high yields when TBDK is used as the catalyst. Control of the coordination sphere of potassium with exogenous chelating ligands, in combination with mechanistic DFT calculations, demonstrated the role and positive influence of the alkali-metal cation on the kinetics.

Actinide complexes possessing six-membered N-heterocyclic iminato moieties: Synthesis and reactivity

A novel class of ligand systems possessing a sixmembered N-heterocyclic iminato [perimidin-2-iminato (PrRN, where R = isopropyl, cycloheptyl)] moiety is introduced. The complexation of these ligands with early actinides (An = Th and U) results in powerful catalysts [(PrRN)An(N{SiMe3)2}3] (3-6) for exigent insertion of alcohols into carbodiimides to produce the corresponding isoureas in short reaction times with excellent yields. Experimental, thermodynamic, and kinetic data as well as the results of stoichiometric reactions provide cumulative evidence that supports a plausible mechanism for the reaction.

Actinide-Catalyzed Intermolecular Addition of Alcohols to Carbodiimides

The unprecedented actinide-catalyzed addition of alcohols to carbodiimides is presented. This represents a rare example of thorium-catalyzed transformations of an alcoholic substrate and the first example of uranium complexes showing catalytic reactivity with alcohols. Using the uranium and thorium amides U[N(SiMe3)2]3 and [(Me3Si)2N]2An[κ2-(N,C)-CH2Si(CH3)2N(SiMe3)] (An = Th or U), alcohol additions to unsaturated carbon-nitrogen bonds are achieved in short reaction times with excellent selectivities and high to excellent yields. Computational studies, supported by experimental thermodynamic data, suggest plausible models of the profile of the reaction which allow the system to overcome the high barrier of scission of the actinide-oxygen bond. Accompanied by experimentally determined kinetic parameters, a plausible mechanism is proposed for the catalytic cycle.