N,N,N-tributyl-1-Butanaminium (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate
[CAS# 1192651-80-1]

Identification

• Name: N,N,N-tributyl-1-Butanaminium (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl sulfate
• Synonyms: Tetrabutylammonium (1R,2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate
• Molecular Formula: C₁₆H₃₆N^.C₇H₁₀N₃O₆S
• Molecular Weight: 506.70
• CAS Registry Number: 1192651-80-1
• EC Number: 812-038-2
• SMILES: CCCC[N+](CCCC)(CCCC)CCCC.C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)[O-])C(=O)N

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H319-H412
• Precautionary Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P351+P338-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovory and Applicatios

N,N,N-tributyl-1-butylamine (1R,2S,5R)-2-(aminocarbonyl)-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl sulfate, often abbreviated for convenience, is a compound discovered through research focused on the synthesis of novel quaternary ammonium salts and diazabicyclo compounds. The compound combines a quaternary ammonium ion with a diazabicyclo moiety, giving it a unique structure that allows for interesting chemical interactions and potential applications. Its synthesis involves the reaction of tributylamine with the corresponding diazabicyclo derivative followed by sulfation to introduce the sulfate group.

The compound is used in catalysis, particularly as a phase transfer catalyst. The quaternary ammonium ion promotes the transfer of anions between aqueous and organic phases, making it valuable in a variety of organic reactions, including nucleophilic substitutions and oxidations. Its structure allows for efficient interactions with reactants, thereby improving reaction rates and selectivity, such as in the synthesis of pharmaceuticals and fine chemicals.

In drug development, the compound can be used as a precursor or intermediate in the synthesis of complex organic molecules. Its quaternary ammonium group can be used to improve the solubility and bioavailability of drug candidates. In addition, the diazabicyclic moiety may interact with biological targets, providing opportunities for drug discovery and development.

The compound is used in organic synthesis as a reagent to introduce quaternary ammonium groups into target molecules. This is very useful for making surfactants, ion exchange resins, and other functional materials. The diazabicyclic structure also serves as a valuable scaffold for building more complex organic frameworks, aiding in the development of new synthetic methods.

Due to its amphiphilic nature, combining hydrophilic quaternary ammonium and hydrophobic butyl chains, the compound is used to formulate surfactants and detergents. These materials are essential in cleaning, emulsification, and dispersion applications ranging from household cleaning products to industrial formulations due to their ability to reduce surface tension and enhance mixing of oil and aqueous phases.

In analytical chemistry, this compound is used as an ion pairing agent in high-performance liquid chromatography (HPLC) and mass spectrometry (MS). Its quaternary ammonium group interacts with ionic analytes, improving separation and detection. This application is essential for analyzing complex mixtures, including pharmaceutical formulations, biological samples, and environmental pollutants.

The structural features of this compound make it a hot topic in biological research, especially in studying interactions with biomolecules such as proteins and nucleic acids. Its unique diazabicyclic core may interact with specific binding sites, providing insights into molecular recognition and potentially aiding the design of new bioactive compounds.