but-3-enoic acid

• ChemBase ID: 109376
• Molecular Formular: C4H6O2
• Molecular Mass: 86.08924
• Monoisotopic Mass: 86.03677943
• SMILES: OC(=O)CC=C
• Canonical SMILES: OC(=O)CC=C
• InChI: InChI=1S/C4H6O2/c1-2-3-4(5)6/h2H,1,3H2,(H,5,6)
• InChIKey: PVEOYINWKBTPIZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: but-3-enoic acid
• IUPAC Traditional name: 3-butenoic acid
• Synonyms: VINYLACETIC ACID; Vinylacetic acid; 3-Butenoic acid; 3-Butenoic acid; Vinylacetic acid; 乙烯基乙酸; 3-丁烯酸; 乙烯基乙酸, 96%, 0.5% 氢醌作为稳定剂

Database IDs

• CAS Number: 625-38-7
• EC Number: 210-892-5
• MDL Number: MFCD00002782
• Beilstein Number: 1699159
• PubChem SID: 24889969; 162094975; 24848176
• PubChem CID: 32743

CALCULATED PROPERTIES

• Acid pKa: 4.7018223
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.24374299
• LogD (pH = 7.4): -2.021534
• Log P: 0.6177708
• Molar Refractivity: 21.9157 cm^3
• Polarizability: 8.399095 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -39 °C(lit.); -39°C
• Boiling Point: 162-163°C; 163 °C(lit.)
• Flash Point: 149 °F; 65 °C; 65°C(149°F)
• Density: 1.009 g/mL at 20 °C; 1.012; 1.013 g/mL at 25 °C(lit.)
• Refractive Index: 1.4240; n20/D 1.423; n20/D 1.423(lit.)

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 2922; UN3265
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 22-34; 22-34-40-43-68; 34
• Safety Statements: 26-36/37/39-45; 26-36/37/39-45-60
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314; H302-H314-H317-H341-H351; H314-H318-H227
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.5% (GC); 96%; 97%
• Grade: purum
• Contains: hydroquinone as inhibitor; hydroquinone as stabilizer
• Linear Formula: CH2=CHCH2COOH

DETAILS

MP Biomedicals - 05210822

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 134716

Application
Used in a preparation of strained nitroso Diels-Aldrer adducts which undergo a domino ROC metathesis in the presence of Ru-carbene catalysts and olefins.1
Packaging
25, 100 g in glass bottle

REFERENCES

• ?-Unsaturated acids, including vinylacetic acid, undergo bromolactonization with bromine in the presence of bicarbonate giving a mixture of ?- and -lactones: J. Org. Chem., 55, 2487 (1990). Further treatment of the lactone mixture with AgNO₃ in acetic acid provides a route to butenolides: Tetrahedron Lett., 34, 1411 (1993).