2-Amino-1,1,1-trifluoropropane
[CAS# 421-49-8]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 2-Amino-1,1,1-trifluoropropane
• Synonyms: (2,2,2-Trifluoro-1-methylethyl)amine
• Molecular Formula: C₃H₆F₃N
• Molecular Weight: 113.08
• CAS Registry Number: 421-49-8
• EC Number: 806-637-8
• SMILES: CC(C(F)(F)F)N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.326, Calc.^*
• Boiling Point: 58.9±35.0 ºC (760 mmHg), Calc.^*, 46-47 ºC (Expl.)
• Flash Point: -1.7±10.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Hazard Statements: H226-H314-H335
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P271-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P319-P321-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Flammable liquids	Flam. Liq.	3	H226
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovory and Applicatios

2-Amino-1,1,1-trifluoropropane (C₃HF₃NH₂) is an organic compound containing both an amino group and a trifluoropropane structure. This substance is a part of a broader class of fluorinated amines, which are of significant interest in various industrial and chemical applications due to the unique properties imparted by the trifluoromethyl group.

The synthesis of 2-amino-1,1,1-trifluoropropane generally involves the introduction of the amino group to a trifluoropropane backbone. This compound is typically produced through controlled reactions, which may include the use of fluorinating reagents and amino group transfer agents to achieve the desired trifluoropropane substitution. The trifluoromethyl group (CF₃) is known for its electron-withdrawing properties, making it an essential feature in the compound’s reactivity.

2-Amino-1,1,1-trifluoropropane is employed in the synthesis of various chemical intermediates and materials. The trifluoromethyl group in this compound has a significant influence on the chemical and physical properties of the resulting materials. The compound can be utilized in the preparation of novel fluorinated molecules that display improved thermal stability, enhanced solubility, and altered chemical reactivity, all of which are beneficial in the development of specialty chemicals and advanced materials.

One of the primary applications of 2-amino-1,1,1-trifluoropropane lies in the field of pharmaceutical chemistry. Fluorine-substituted compounds are widely studied for their potential biological activity, and the introduction of the trifluoromethyl group can influence the pharmacokinetics and pharmacodynamics of drug candidates. Although 2-amino-1,1,1-trifluoropropane itself is not typically a drug, it can serve as a valuable intermediate for the synthesis of fluorinated pharmaceutical compounds. These compounds may exhibit enhanced metabolic stability, improved binding affinity to target proteins, and altered distribution in biological systems.

In addition to its pharmaceutical applications, 2-amino-1,1,1-trifluoropropane is of interest in the synthesis of agrochemicals. The unique characteristics of fluorinated amines can improve the effectiveness of herbicides, fungicides, and insecticides. By introducing a trifluoromethyl group into agrochemical molecules, researchers can enhance their potency and resistance to degradation, making them more effective in controlling pests and diseases in agriculture.

Furthermore, 2-amino-1,1,1-trifluoropropane is also utilized in the development of new materials. The fluorine atom, especially when attached to a carbon chain such as in the trifluoropropane structure, imparts notable properties like hydrophobicity, high chemical resistance, and low surface energy. These properties are valuable in industries such as coatings, lubricants, and advanced polymers, where durability and resistance to environmental stressors are essential.

Although the compound has various applications, its handling requires care due to the potentially hazardous nature of fluorinated chemicals. The trifluoromethyl group can contribute to increased toxicity and persistence in the environment, which necessitates responsible management during its synthesis, use, and disposal. Like many fluorinated compounds, 2-amino-1,1,1-trifluoropropane may exhibit long-term environmental stability, which raises concerns about bioaccumulation and ecological impact. As such, regulatory measures and environmental guidelines are important considerations when working with this and similar chemicals.

In summary, 2-amino-1,1,1-trifluoropropane is a versatile fluorinated amine with applications in organic synthesis, pharmaceuticals, agrochemicals, and materials science. Its trifluoromethyl group imparts unique chemical properties that make it a valuable building block for the development of novel chemicals with improved stability, bioactivity, and effectiveness. However, due to environmental and safety concerns, the use of this compound should be carefully managed to minimize its ecological footprint.

References

2013. Chemoenzymatic dynamic kinetic resolution of a-trifluoromethylated amines: influence of substitutions on the reversed stereoselectivity. RSC Advances, 3(25).
DOI: 10.1039/c3ra40526e

2011. Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone. Org. Biomol. Chem., 9(20).
DOI: 10.1039/C1OB05813D