Ethyl 3-amino-4,4,4-trifluorocrotonate
[CAS# 372-29-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Ethyl 3-amino-4,4,4-trifluorocrotonate
• Synonyms: Ethyl 3-amino-4,4,4-trifluoro-2-butenoate
• Molecular Formula: C₆H₈F₃NO₂
• Molecular Weight: 183.13
• CAS Registry Number: 372-29-2
• EC Number: 609-360-9
• SMILES: CCOC(=O)/C=C(/C(F)(F)F)N

Properties

• Density: 1.245
• Boiling point: 55-56 °C (15 mmHg)
• Refractive index: 1.421-1.425
• Flash point: 64 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H302-H312-H315-H318-H319-H331-H332-H335-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	3	H331

Discovery and Applications

Ethyl 3-amino-4,4,4-trifluorocrotonate is an organic compound that belongs to the class of trifluoromethylated crotonate derivatives. It consists of a crotonate (a β,β-unsaturated ester) structure with an amino group at the 3-position and a trifluoromethyl group attached to the 4-position. This compound has attracted attention due to its chemical reactivity and its potential applications in various fields, including organic synthesis and medicinal chemistry.

The discovery of ethyl 3-amino-4,4,4-trifluorocrotonate is linked to the broader interest in trifluoromethylated compounds, which have gained significance for their ability to modulate the electronic properties of organic molecules. Trifluoromethyl groups are known to enhance the lipophilicity, metabolic stability, and pharmacological properties of compounds, making them attractive for drug design. The development of ethyl 3-amino-4,4,4-trifluorocrotonate can be seen as part of the ongoing effort to explore trifluoromethylated systems and their diverse applications.

In organic synthesis, ethyl 3-amino-4,4,4-trifluorocrotonate has been utilized as an intermediate for the synthesis of more complex compounds. Its reactivity, especially the presence of the conjugated double bond, allows it to participate in various chemical reactions, such as Michael additions and nucleophilic substitutions. The trifluoromethyl group enhances the electrophilicity of the molecule, making it a useful substrate for further functionalization and the creation of novel fluorinated materials.

One of the most promising applications of ethyl 3-amino-4,4,4-trifluorocrotonate lies in the field of medicinal chemistry. The incorporation of trifluoromethyl groups into organic molecules has been shown to improve the pharmacokinetic properties of compounds, making them more potent and selective in biological systems. Ethyl 3-amino-4,4,4-trifluorocrotonate and its derivatives have been investigated for their potential as building blocks in the design of drug candidates with improved properties, such as enhanced stability, bioavailability, and target specificity.

Additionally, this compound holds promise for the development of new materials and agrochemicals. Its chemical properties make it suitable for use in the synthesis of polymers, specialty chemicals, and agrochemical agents, where the trifluoromethyl group can contribute to improved performance, such as resistance to degradation and increased efficiency.

References

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