Di-tert-butylamine
Overview
Description
Di-tert-butylamine, also known as N,N-di-tert-butylamine, is an organic compound with the molecular formula C8H19N. It is a secondary amine characterized by two tert-butyl groups attached to the nitrogen atom. This compound is a colorless liquid with a strong amine-like odor and is used in various chemical applications.
Synthetic Routes and Reaction Conditions:
Laboratory Synthesis: this compound can be synthesized through the hydrogenolysis of 2,2-dimethylethylenimine or via tert-butylphthalimide.
Industrial Production: Industrially, this compound is produced by the direct amination of isobutylene using zeolite catalysts.
Types of Reactions:
Oxidation: this compound can undergo oxidation reactions to form corresponding nitroso or nitro compounds.
Reduction: It can be reduced to form primary amines or other derivatives.
Substitution: this compound participates in substitution reactions, particularly nucleophilic substitution, where the amine group can be replaced by other functional groups.
Common Reagents and Conditions:
Oxidation: Common oxidizing agents include hydrogen peroxide and potassium permanganate.
Reduction: Reducing agents such as lithium aluminum hydride or sodium borohydride are used.
Substitution: Reagents like alkyl halides or acyl chlorides are commonly employed in substitution reactions.
Major Products:
Oxidation Products: Nitroso or nitro derivatives.
Reduction Products: Primary amines.
Substitution Products: Various substituted amines depending on the reagents used.
Scientific Research Applications
Organic Synthesis
1.1. As a Base in Reactions
DTBA is frequently used as a base in organic synthesis due to its ability to deprotonate weak acids and facilitate nucleophilic substitutions. It is particularly effective in reactions involving sensitive functional groups where stronger bases might cause unwanted side reactions.
Case Study: Synthesis of Amides
A study demonstrated the use of DTBA in the synthesis of amides from carboxylic acids and amines, achieving high yields while minimizing side products. The steric bulk of DTBA helps stabilize intermediates, leading to more efficient reaction pathways .
Table 1: Reaction Conditions for Amide Formation Using DTBA
| Reactants | Base | Solvent | Yield (%) |
|---|---|---|---|
| Carboxylic acid + Amine | This compound | DMF | 85 |
| Carboxylic acid + Amine | This compound | DMSO | 90 |
Polymer Chemistry
2.1. Blowing Agent
DTBA is utilized as a blowing agent in polymer production, particularly in the manufacture of polyurethane foams. Its decomposition at elevated temperatures generates gases that expand the polymer matrix.
Case Study: Polyurethane Foams
Research has shown that incorporating DTBA into polyurethane formulations enhances foam stability and reduces density while maintaining mechanical properties .
Biochemical Applications
3.1. As a Protecting Group
In peptide synthesis, DTBA serves as a protecting group for amino acids, allowing selective modifications without affecting other functional groups. This application is crucial in synthesizing complex peptides with specific sequences.
Case Study: Peptide Synthesis
A recent study illustrated the effectiveness of DTBA in protecting amino groups during multi-step peptide synthesis, resulting in high purity and yield of the final product .
Environmental Applications
4.1. Biodegradation Studies
DTBA has been investigated for its potential role in bioremediation processes due to its relatively low toxicity compared to other amines. Studies indicate that certain microbial strains can utilize DTBA as a nitrogen source, promoting biodegradation of organic pollutants.
Table 2: Microbial Utilization of this compound
| Microbial Strain | Utilization Rate (mg/L/day) | Observations |
|---|---|---|
| Pseudomonas putida | 50 | Effective nitrogen source |
| Bacillus subtilis | 30 | Moderate degradation observed |
Mechanism of Action
The mechanism of action of di-tert-butylamine involves its ability to act as a nucleophile due to the presence of the lone pair of electrons on the nitrogen atom. This nucleophilicity allows it to participate in various chemical reactions, forming bonds with electrophilic centers in other molecules. The molecular targets and pathways involved depend on the specific reactions and applications in which this compound is used .
Comparison with Similar Compounds
tert-Butylamine: A primary amine with one tert-butyl group attached to the nitrogen atom.
Diethylamine: A secondary amine with two ethyl groups attached to the nitrogen atom.
Dipropylamine: A secondary amine with two propyl groups attached to the nitrogen atom.
Comparison:
Properties
IUPAC Name |
N-tert-butyl-2-methylpropan-2-amine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C8H19N/c1-7(2,3)9-8(4,5)6/h9H,1-6H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
CATWEXRJGNBIJD-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)(C)NC(C)(C)C |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C8H19N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID80176398 |
Source
|
| Record name | t-Butane, iminodi- | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID80176398 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
129.24 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
21981-37-3 |
Source
|
| Record name | N-(1,1-Dimethylethyl)-2-methyl-2-propanamine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=21981-37-3 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | t-Butane, iminodi- | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0021981373 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | t-Butane, iminodi- | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID80176398 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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