Description

Ethyl 3-amino-4,4,4-trifluoro-2-butenoate (CAS No. 372-29-2) is a high-purity fluorinated organic compound with the molecular formula C₆H₈F₃NO₂. This specialized ester is widely utilized in pharmaceutical research, agrochemical synthesis, and advanced material science due to its unique trifluoromethyl group and reactive amino functionality. The compound exhibits excellent stability under standard laboratory conditions and is supplied as a clear to pale-yellow liquid with ≥98% purity (GC). It serves as a versatile building block for the synthesis of trifluoromethyl-substituted heterocycles, peptidomimetics, and bioactive molecules. Suitable for use in nucleophilic addition reactions, Michael additions, and palladium-catalyzed cross-couplings. Packaged under inert gas in amber glass bottles to ensure prolonged shelf life.

Key Features:
• High chemical purity (≥98%)
• Trifluoromethyl group enhances lipophilicity and metabolic stability
• Reactive amino and ester functionalities for diverse derivatization
• Compatible with organometallic catalysis
• Ideal for medicinal chemistry and drug discovery applications

Properties

• CAS Number: 372-29-2
• Complexity: 197
• IUPAC Name: ethyl 3-amino-4,4,4-trifluoro-but-2-enoate
• InChI: InChI=1S/C6H8F3NO2/c1-2-12-5(11)3-4(10)6(7,8)9/h3H,2,10H2,1H3
• InChI Key: NXVKRKUGIINGHD-UHFFFAOYSA-N
• Exact Mass: 183.05071298
• Molecular Formula: C6H8F3NO2
• Molecular Weight: 183.13
• SMILES: CCOC(=O)C=C(C(F)(F)F)N
• Topological: 52.3
• Monoisotopic Mass: 183.05071298
• Physical Description: Liquid
• Synonyms: 372-29-2, Ethyl 3-amino-4,4,4-trifluoro-2-butenoate, ethyl 3-amino-4,4,4-trifluorobut-2-enoate, MFCD00068195, (E)-Ethyl 3-amino-4,4,4-trifluorocrotonate, SCHEMBL713656, DTXSID001270040, AKOS025243620, ethyl 3-amino-4,4,4-trifluorobutenoate, SY021559, DB-049083, DB-264958, ethyl 4,4,4-trifluoro-3-amino-2-butenoate, NS00122421, 3-amino-4,4,4-trifluoro-2-butenoic acid ethyl ester, 4,4,4-trifluoro-3-amino-2-butenoic acid ethyl ester

Ethyl 3-amino-4,4,4-trifluoro-2-butenoate is primarily employed as a key intermediate in the synthesis of fluorinated pharmaceuticals, particularly CNS-active compounds and kinase inhibitors. Its trifluoromethyl group improves membrane permeability in drug candidates, while the amino-ester moiety allows for facile conversion to amides or heterocycles. Researchers utilize this compound to develop novel PET radiotracers due to fluorine-19’s NMR sensitivity. In material science, it serves as a precursor for fluorinated liquid crystals and OLED materials.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (88.1%)
• Acute Tox. 4 (69.5%)
• Skin Irrit. 2 (22%)
• Eye Dam. 1 (18.6%)
• Eye Irrit. 2 (72.9%)
• Acute Tox. 3 (18.6%)
• Acute Tox. 4 (67.8%)
• STOT SE 3 (71.2%)
• Aquatic Chronic 3 (18.6%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.