buta-1,3-dien-1-yl acetate

• ChemBase ID: 149702
• Molecular Formular: C6H8O2
• Molecular Mass: 112.12652
• Monoisotopic Mass: 112.0524295
• SMILES: CC(=O)O/C=C/C=C
• Canonical SMILES: CC(=O)O/C=C/C=C
• InChI: InChI=1S/C6H8O2/c1-3-4-5-8-6(2)7/h3-5H,1H2,2H3
• InChIKey: NMQQBXHZBNUXGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: buta-1,3-dien-1-yl acetate; (1E)-buta-1,3-dien-1-yl acetate
• IUPAC Traditional name: 1,3-butadien-1-ol, acetate; (1E)-buta-1,3-dien-1-yl acetate
• Synonyms: 1,3-Butadienyl acetate; 1-Acetoxy-1,3-butadiene; Crotonaldehyde enol acetate; 1,3-Butadienylacetate; 1-Acetoxy-1,3-butadiene, cis + trans; 1-乙酰氧基-1,3-丁二烯; 1-乙酰氧基-1,3-丁二烯, 顺式 + 反式

Database IDs

• CAS Number: 1515-76-0
• EC Number: 216-159-6
• MDL Number: MFCD00008714
• Beilstein Number: 1743394
• PubChem SID: 162243864; 24853196
• PubChem CID: 5363433

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.9544384
• LogD (pH = 7.4): 0.9544384
• Log P: 0.9544384
• Molar Refractivity: 31.4236 cm^3
• Polarizability: 12.063753 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 51-52°C/30mm; 60-61 °C/40 mmHg(lit.)
• Flash Point: 33 °C; 33°C(91°F); 91.4 °F
• Density: 0.945; 0.945 g/mL at 25 °C(lit.)
• Refractive Index: 1.4690; n20/D 1.469(lit.)
• Vapor Pressure: 40 mmHg ( 60 °C)

Safety Information

• RTECS: EJ1225000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• UN Number: 1992; UN1992
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-21/22-36/37/38; 10-22-24-36/37/38
• Safety Statements: 20-23-26-27-36/37/39-45; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H311-H315-H319-H335; H311-H302-H315-H319-H335-H226
• GHS Precautionary statements: P210-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P305 + P351 + P338-P312
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1992 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 90+%, stab. with 0.1% 4-tert-butylcatechol
• Contains: 0.1% p-tert-butylcatechol as stabilizer
• Linear Formula: CH2=CHCH=CHOCOCH3

DETAILS

Sigma Aldrich - 220868

Packaging
10 g in glass bottle
Application
Diels-Alder diene for reaction:
• With dienophiles such as maleimides,1 a juglone,2 a butyne-1,4-dione,3 and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate4
• Via visible light photocatalysis5Reactant involved in intermolecular oxa-Pictet-Spengler cyclization6

REFERENCES

• Undergoes regiospecific cycloadditions with a variety of electron-deficient dienophiles: J. Am. Chem. Soc.,84, 4591 (1962); 100, 313 (1978); J. Org. Chem., 44, 4299 (1979); Tetrahedron Lett.,353, 2289, 4023 (1978).