tert-Butylamine
[CAS# 75-64-9]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: tert-Butylamine
• Synonyms: 2-Amino-2-methylpropane
• Molecular Formula: C₄H₁₁N
• Molecular Weight: 73.14
• CAS Registry Number: 75-64-9
• EC Number: 200-888-1
• SMILES: CC(C)(C)N

Properties

• Density: 0.696
• Melting point: -67 ºC
• Boiling point: 46 ºC
• Refractive index: 1.377-1.379
• Flash point: -9 ºC
• Water solubility: MISCIBLE

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07 Danger
• Hazard Statements: H225-H301-H302-H314-H318-H331-H412
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1A	H314
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	2	H300
Skin corrosion	Skin Corr.	1B	H314

• Transport Information: UN 3286

Discovory and Applicatios

Tert-butylamine is a branched-chain amine that has gained prominence in various fields of chemistry and industry. Its discovery dates back to the early 20th century, coinciding with the growing interest in amines as fundamental organic compounds. Tert-butylamine is synthesized through several methods, with the most common being the alkylation of ammonia with tert-butanol or through the reduction of tert-butyl isocyanate. The resulting compound features a three-dimensional, branched structure that imparts unique physical and chemical properties, making it a valuable building block in organic synthesis.

One of the primary applications of tert-butylamine lies in the synthesis of pharmaceuticals. It serves as a key intermediate in the production of various active pharmaceutical ingredients (APIs). The compound's amine functionality allows for the formation of various derivatives, which can enhance biological activity and efficacy. For example, tert-butylamine derivatives have been explored in the development of anti-inflammatory and analgesic medications. The structural modifications achieved using tert-butylamine as a starting material can lead to compounds that target specific biological pathways, thereby improving therapeutic outcomes.

In addition to pharmaceuticals, tert-butylamine is widely utilized in the production of agricultural chemicals. Its derivatives have shown promise as herbicides and fungicides, contributing to the enhancement of crop yields and protection against pests and diseases. The ability to modify tert-butylamine to develop more effective agrochemicals is an area of active research, with studies focusing on optimizing their selectivity and reducing environmental impact.

The chemical properties of tert-butylamine also make it suitable for use as a solvent and a reagent in organic synthesis. Its relatively low boiling point and high solubility in water enable its use in various chemical reactions. Tert-butylamine has been employed in reactions such as nucleophilic substitutions and as a catalyst in the formation of amides and other nitrogen-containing compounds. Moreover, its role as a building block in polymer chemistry is noteworthy. Tert-butylamine can be incorporated into polymer chains to enhance the properties of materials, such as improving thermal stability and mechanical strength.

Furthermore, tert-butylamine has applications in the manufacture of surfactants and detergents. The compound can be used to synthesize quaternary ammonium compounds, which are widely utilized in cleaning products for their ability to reduce surface tension and enhance cleaning efficiency. This application is particularly important in industrial and household cleaning formulations.

Research into tert-butylamine's potential as a chiral auxiliary has gained traction in recent years. The compound's structure allows for the development of asymmetric synthesis techniques, which are crucial in the production of enantiomerically pure compounds. This property is especially relevant in the pharmaceutical industry, where the efficacy of a drug can depend significantly on its stereochemistry.

Safety and environmental considerations are also essential when discussing tert-butylamine. While the compound is generally regarded as safe when handled appropriately, it can be harmful if ingested or inhaled. Proper safety protocols must be followed during its synthesis and application to minimize exposure and environmental release.

In summary, tert-butylamine is a versatile chemical compound with significant applications in pharmaceuticals, agrochemicals, organic synthesis, and materials science. Its discovery has paved the way for various advancements in these fields, highlighting its importance as a building block for developing new compounds and materials. Ongoing research continues to explore its potential, ensuring that tert-butylamine remains a subject of interest in both academic and industrial chemistry.