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

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

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

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

Downstream Products

• 17087-29-5 α-alaninebetaine 
• 56755-22-7 L-N,N,N-trimethylphenylalanine 
• 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 
• 103-26-4 Methyl cinnamate 
• 4358-87-6 (RS)-methyl mandelate 
• 81505-49-9 (S)-(-)-Methyl 2-[(tert-butoxycarbonyl)amino]-6-hydroxypentanoate 
• 81505-49-9 (D,L)-N-Boc-ε-hydroxynorleucine methyl ester 
• 13673-95-5 (S)-methyl 2-hydroxy-3-phenylpropanoate 
• 5539-66-2 1-hydroxy-8-methoxyanthraquinone 
• 56595-17-6 Anthopleurine 
• 56595-17-6 C₇H₁₅NO₄ 
• 56595-17-6 (2S,3R)-2,3-dihydroxy-4-(trimethylammonium)butanoate 

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.

Synthetic method for isourea catalyzed by rare-earth compound

The invention relates to a synthetic method for isourea catalyzed by a rare-earth compound. The synthetic method comprises the following steps: (1) enabling carbodiimide which is as shown in a formula (1) and alcohol which is as shown in a formula (2) to react at 25 to 60 DEG C under the catalytic action of rare earth amine to obtain the isourea, wherein the structural formulae of the formula (1) and the formula (2) are as shown in the description, wherein R1 and R2 are independently selected from C3-C8 alkyls or aryls; R3 is C1-C3 alkyls or substituted benzyls, wherein the substituted benzyls are the benzyls which contain a methyl, a naphthyl, a halogen or a pyridine ring; the rare earth amine is one of lanthanum tris[N,N-bis(trimethylsilane)amide], neodymium tris[N,N-bis(trimethylsilane)amide], samarium tris[N,N-bis(trimethylsilane)amide] or ytterbium tris[N,N-bis(trimethylsilane)amide]. According to the method, raw materials are easily obtained; the operation is simple and convenient; conditions of an application method are mild; the yield is high; the substrate application range is wide.

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.

Catalytic Addition of Alcohols into Carbodiimides Promoted by Organoactinide Complexes

The insertion of alcohols into carbodiimides mediated by benzimidazolin-2-iminato actinide complexes [(BimR1/R2N)AnN3] [N = N(SiMe3)2] is presented herein. Analysis of single-crystal data revealed that steric hindrance, rather than electronic properties, plays an important role in determining the accessibility for this insertion process. All actinide complexes showed excellent activities under very mild conditions. Stoichiometric reactions in combination with kinetic and thermodynamic studies allow us to propose a plausible active species and a mechanism for the catalytic cycle.

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.

A novel synthesis of 2-alkylthiobenzothiazoles and 2-alkylthiobenzoxazoles

3H-Benzothiazole-2-thione and 3H-benzoxazole-2-thione were selectively S-alkylated by use of O-alkylisoureas as the alkylating reagents. The reactions could be performed under mild reaction conditions in short reaction times, and high yields were obtained using O-primary-alkylisoureas, whereas low yields were obtained with sec-and tert-alkylisoureas.