1-Acetoxy-1,3-Butadiene

Base Information

• Chemical Name: 1-Acetoxy-1,3-Butadiene
• CAS No.: 1515-76-0
• Molecular Formula: C6H8 O2
• Molecular Weight: 112.128
• Hs Code.: 2915390090
• DSSTox Substance ID: DTXSID401030795
• Mol file: 1515-76-0.mol

Synonyms:1,3-Butadien-1-ol,acetate (6CI,7CI,8CI,9CI); 1,3-Butadienyl acetate; 1-Acetoxy-1,3-butadiene;1-Acetoxybutadiene; Butadienyl acetate

Chemical Property of 1-Acetoxy-1,3-Butadiene

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow viscous liquid
• Vapor Pressure: 40 mm Hg ( 60 °C)
• Refractive Index: n20/D 1.47
• Boiling Point: 141°Cat760mmHg
• Flash Point: 33.3°C
• PSA: 26.30000
• Density: 0.936g/cm³
• LogP: 1.24920
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 114

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Acetoxy-1,3-butadiene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 10-21/22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OC=CC=C
• Uses: 1-Acetoxy-1,3-butadiene was used as diene in the following reactions:Diels-Alder reaction with ortho-carbazolequinones to yield benzocarbazolequinone.Diels-Alder reaction with diethyl ketovinylphosphonate, with and without Lewis acid assistance.Diels-Alder reaction with methyl acrylate to yield racemic forms of 2-hydroxy-3-cyclohexenecarboxylic acid. It was used for the reaction with dienophiles such as maleimides, a juglone, a butyne-1,4-dione and methyl 2-(4-methylphenyl)-2H-azirine-3-carboxylate and during visible light photocatalysis. It was also used as reactant during intermolecular oxa-Pictet-Spengler cyclization.

Technology Process of 1-Acetoxy-1,3-Butadiene

There total 28 articles about 1-Acetoxy-1,3-Butadiene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.4%

acetic anhydride (108-24-7) + crotonaldehyde (123-73-9,4170-30-3) → 1-acetoxybuta-1,3-diene (1515-76-0,35694-19-0,35694-20-3)

Guidance literature:

With dmap; triethylamine; In neat (no solvent); at 20 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0034-1378230

Reference yield: 69.0%

acetyl chloride (75-36-5) + crotonaldehyde (123-73-9,4170-30-3) → 1-acetoxybuta-1,3-diene (1515-76-0,35694-19-0,35694-20-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.bmcl.2012.01.006

Reference yield: 58.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + Isopropenyl acetate (108-22-5) → 1-acetoxybuta-1,3-diene (1515-76-0,35694-19-0,35694-20-3)

Guidance literature:

at 80 ℃;

DOI:10.1016/S0040-4039(96)02017-5

upstream raw materials:

trans-Crotonaldehyde

Isopropenyl acetate

acetic anhydride

crotonaldehyde

Downstream raw materials:

1-acetoxy-5-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene

1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene

2,3-dimethoxy-1,4-naphthoquinone

N,N'-(naphthalene-1,4-diyl)bis(4-chlorobenzenesulfonamide)

Refernces

• 1、 Georgieff,Dupre. "". . p. 1070,1071, 1073. Retrieved 1960.
• 2、 Schubert,Lanka. "". . p. 1956. Retrieved 1954.
• 3、 -. "METHOD FOR PRODUCING 1-ACYLOXY-1,3-BUTADIENE". Paragraph 0024; 0025-0026. . Retrieved 2018/09/11.
• 4、 B?se, Dietrich,Frey, Wolfgang,Pietruszka, J?rg. "The 'Mikami'-catalyst in enantioselective diels-alder reactions of juglone-based dienophiles with different 1-oxygenated dienes: An investigation on the substitution pattern dependent regioselectivity". supporting information. p. 2524 - 2532. Retrieved 2014/11/08.