ethyl (2E)-4,4,4-trifluorobut-2-enoate

• ChemBase ID: 6553
• Molecular Formular: C6H7F3O2
• Molecular Mass: 168.1137896
• Monoisotopic Mass: 168.03981412
• SMILES: O=C(/C=C/C(F)(F)F)OCC
• Canonical SMILES: CCOC(=O)/C=C/C(F)(F)F
• InChI: InChI=1S/C6H7F3O2/c1-2-11-5(10)3-4-6(7,8)9/h3-4H,2H2,1H3/b4-3+
• InChIKey: ZKRJCMKLCDWROR-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2E)-4,4,4-trifluorobut-2-enoate; ethyl 4,4,4-trifluorobut-2-enoate
• IUPAC Traditional name: ethyl (2E)-4,4,4-trifluorobut-2-enoate; ethyl 4,4,4-trifluorobut-2-enoate
• Synonyms: Ethyl 4,4,4-trifluorocrotonate; Ethyl 4,4,4-trifluoro-trans-2-butenoate; Ethyl 4,4,4-trifluorocrotonate; ethyl (2E)-4,4,4-trifluorobut-2-enoate; 4,4,4-Trifluorocrotonic acid ethyl ester; Ethyl trans-4,4,4-trifluorobut-2-enoate; Ethyl (2E)-4,4,4-trifluorobut-2-enoate; Ethyl 4,4,4-trifluorocrotonate 98%; 4,4,4-三氟丁烯酸乙酯; 4,4,4-三氟巴豆酸乙酯

Database IDs

• CAS Number: 25597-16-4
• EC Number: 000-000-0
• MDL Number: MFCD00009903
• Beilstein Number: 1707262
• PubChem SID: 160969860; 24856340
• PubChem CID: 5371261

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.0200448
• LogD (pH = 7.4): 2.0200448
• Log P: 2.0200448
• Molar Refractivity: 33.4151 cm^3
• Polarizability: 11.939404 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 113-115°C; 114-115 °C(lit.); 114-115°C
• Flash Point: 25°C; 25°C(77°F); 26 °C; 78.8 °F
• Density: 1.125; 1.125 g/mL at 25 °C(lit.)
• Refractive Index: 1.3601; n20/D 1.3601(lit.)
• Hydrophobicity(logP): 1.264

Safety Information

• Storage Warning: Flammable; LACHRYMATOR, FLAMMABLE
• European Hazard Symbols: Irritant (Xi)
• UN Number: 3272; UN3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37; 10-36/37/38
• Safety Statements: 16-26-27-28-36/37/39; 23-26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335; H226-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3

Product Information

• Purity: 95%; 98%
• Linear Formula: CF3CH=CHCO2C2H5

DETAILS

Apollo Scientific Ltd - PC3282

JOC., 60, 4363 (1995): Paper discusses the much greater reactivity towards Michael additions cf. non-fluorinated crotonates, giving anti-adducts with high selectivity.

Sigma Aldrich - 269697

Packaging
5 g in glass bottle

REFERENCES

• Shows significantly greater reactivity towards Michael additions than Ethyl crotonate, A12529, providing anti-adducts with good selectivity: J. Org. Chem., 60, 4363 (1995):