Acetoxymethyl vinyl ketone

Base Information

• Chemical Name: Acetoxymethyl vinyl ketone
• CAS No.: 38982-28-4
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 2915390090
• European Community (EC) Number: 878-742-7
• DSSTox Substance ID: DTXSID60393783
• Nikkaji Number: J799.455I
• Wikidata: Q82192725
• Mol file: 38982-28-4.mol

Synonyms:ACETOXYMETHYL VINYL KETONE;38982-28-4;2-oxobut-3-enyl acetate;2-OXOBUT-3-EN-1-YL ACETATE;ghl.PD_Mitscher_leg0.411;SCHEMBL3993685;DTXSID60393783;GZNCCNHJQSRXNU-UHFFFAOYSA-N;Acetic acid 2-oxo 3-butenyl ester;AKOS006277006;AB16085;FT-0661107

Chemical Property of Acetoxymethyl vinyl ketone

Chemical Property:

• Appearance/Colour: Colourless oil
• Boiling Point: 176.5 °C at 760 mmHg
• Flash Point: 65 °C
• PSA: 43.37000
• Density: 1.039 g/cm³
• LogP: 0.30460
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

Acetoxymethyl Vinyl Ketone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C=C

Technology Process of Acetoxymethyl vinyl ketone

There total 16 articles about Acetoxymethyl vinyl ketone 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: 70.0%

1,4-dihydroxybut-2-yne (110-65-6) + acetic anhydride (108-24-7) → 1-acetoxybut-3-en-2-one (38982-28-4)

Guidance literature:

With sulfuric acid; acetic acid; mercury(II) oxide; 1.) 120-130 deg C, 2 h, 2.) 50-60 deg C, 0.5 h;

Reference yield: 53.0%

2-butyn-1,4-diol diacetate (1573-17-7) → 1-acetoxybut-3-en-2-one (38982-28-4)

Guidance literature:

With sulfuric acid; mercury ion;

DOI:10.1055/s-2006-950193

Reference yield:

sodium acetate (127-09-3) + (4-hydroxy-1-butynyl)phenyliodonium tetrafluoroborate → 1-acetoxybut-3-en-2-one (38982-28-4) + 1,4-diacetoxy-2-butanone (33245-14-6)

Guidance literature:

With water; In tetrahydrofuran; for 0.5h; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jo00278a012

upstream raw materials:

4-acetoxy-2-butyn-1-ol

2-butyn-1,4-diol diacetate

1,4-diacetoxy-2-butanone

1,4-dihydroxy-2-butanone

Downstream raw materials:

2-Oxo-4-phthalimido-1-butyl acetate

2-<2-<(4-methoxybenzyl)oxy>-3-cyclohexen-1-yl>-2-propen-1-ol 1-acetate

Acetic acid 2-[2-(1-benzyl-4,4-dimethyl-2,6-dioxo-cyclohexyl)-ethyl]-[1,3]dioxolan-2-ylmethyl ester

Acetic acid 2-[2-(1-allyl-4,4-dimethyl-2,6-dioxo-cyclohexyl)-ethyl]-[1,3]dioxolan-2-ylmethyl ester

Refernces

• 1、 Jogi, Artur,Paju, Anne,Pehk, Tonis,Kailas, Tiiu,Mueuerisepp, Aleksander-Mati,Kanger, Tonis,Lopp, Margus. "Asymmetric synthesis of 2-aryl-5-oxotetrahydrofuran-2-carboxylic acids". . p. 3031 - 3036. Retrieved 2008/02/08.
• 2、 Ochiai, Masahito,Kunishima, Munetaka,Fuji, Kaoru,Nagao, Yoshimitsu. "Conjugate Addition of Acyloxy Groups to Alkynylphenyliodonium Tetrafluoroborates under Both Basic and Acidic Conditions. Synthesis of α-Acyloxy Ketones". . p. 4038 - 4041. Retrieved 2007/10/02.