2-tert-Butyl-1,3-diisopropylisourea
[CAS# 71432-55-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphorous compound
• Name: 2-tert-Butyl-1,3-diisopropylisourea
• Synonyms: O-tert-Butyl-N,N'-diisopropylisourea; tert-Butyl N,N'-dipropan-2-ylcarbamimidate
• Molecular Formula: C₁₁H₂₄N₂O
• Molecular Weight: 200.32
• CAS Registry Number: 71432-55-8
• EC Number: 846-712-2
• SMILES: CC(C)NC(=NC(C)C)OC(C)(C)C

Properties

• Solubility: Very slightly soluble (0.3 g/L) (25 ºC), Calc.^*
• Density: 0.89±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

2-tert-Butyl-1,3-diisopropylisourea is an organic compound belonging to the isourea class, characterized by the presence of an isourea functional group substituted at the nitrogen atoms and at the 2-position with bulky alkyl groups. The molecular structure consists of a central urea-derived core where the nitrogen atoms are each substituted with isopropyl groups, and the carbon atom adjacent to the nitrogen atoms is bonded to a tert-butyl group. This substitution pattern imparts unique steric and electronic properties to the molecule.

The compound was first synthesized in the context of exploring substituted isoureas for their potential utility as ligands and organocatalysts. Methods for its preparation typically involve the reaction of appropriate isocyanates or carbodiimides with secondary amines or alkylated urea derivatives under controlled conditions. The tert-butyl group at the 2-position introduces significant steric bulk, influencing the conformation and reactivity of the molecule.

2-tert-Butyl-1,3-diisopropylisourea has been studied primarily for its applications in coordination chemistry and catalysis. Its bulky substituents confer steric hindrance that can influence the coordination environment when used as a ligand with transition metals. The isourea moiety can act as a bidentate ligand through the nitrogen and oxygen atoms, allowing it to stabilize metal centers in specific oxidation states or geometries.

In organocatalysis, substituted isoureas including 2-tert-butyl-1,3-diisopropylisourea have shown utility as catalysts or catalyst components in reactions such as the addition of nucleophiles to electrophiles, where hydrogen bonding and steric effects enhance selectivity and reaction rates. Its steric profile can favor particular reaction pathways or suppress side reactions.

The compound's thermal stability and solubility profile make it suitable for use in homogeneous catalytic systems. It can be dissolved in a range of organic solvents, facilitating its application in various synthetic methodologies.

Beyond catalysis, 2-tert-butyl-1,3-diisopropylisourea has found application in materials chemistry as a precursor or stabilizer for the synthesis of certain functional polymers and coordination polymers. Its bulky nature can affect polymer morphology and physical properties when incorporated into polymeric frameworks.

Industrial or large-scale applications remain limited, primarily because of the specialized nature of the compound and its synthesis. However, it is of considerable interest in academic and industrial research laboratories focused on developing new catalysts and ligand systems for organic synthesis and transition metal catalysis.

In summary, 2-tert-butyl-1,3-diisopropylisourea is a sterically hindered isourea derivative valued for its ligand properties and catalytic potential. Its synthesis, structural features, and applications in catalysis and materials science are well documented and serve as the basis for ongoing studies in organometallic chemistry and synthetic methodology development.

References

2009. Straightforward Total Synthesis of 2-O-Feruloyl-l-malate, 2-O-Sinapoyl-l-malate and 2-O-5-Hydroxyferuloyl-l-malate, Synthesis (21)
DOI: 10.1055/s-0029-1216983

2024. Improved synthesis of two quisqualic acid analogs containing hydantoin and imidazolidinone moieties, Chemistry of Heterocyclic Compounds (60)
DOI: 10.1007/s10593-024-03331-1