Isopropenyl acetate

Base Information

• Chemical Name: Isopropenyl acetate
• CAS No.: 108-22-5
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 2915 39 00
• European Community (EC) Number: 203-562-7
• NSC Number: 8262,2197
• UN Number: 2403
• UNII: 4AR9LAS337
• DSSTox Substance ID: DTXSID3031492
• Nikkaji Number: J35.907F
• Wikipedia: Isopropenyl_acetate
• Wikidata: Q27259352
• Metabolomics Workbench ID: 45451
• ChEMBL ID: CHEMBL1385681
• Mol file: 108-22-5.mol

Synonyms:isopropenyl acetate

Chemical Property of Isopropenyl acetate

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 31.4mmHg at 25°C
• Melting Point: -93 °C
• Refractive Index: n20/D 1.401(lit.)
• Boiling Point: 97 °C at 760 mmHg
• Flash Point: 12.9 °C
• PSA: 26.30000
• Density: 0.914 g/cm³
• LogP: 1.08310
• Storage Temp.: Flammables area
• Solubility.: 34g/l
• Water Solubility.: 34 g/L (20 ºC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 94.3
• Transport DOT Label: Flammable Liquid

Purity/Quality:

97% ^*data from raw suppliers

Isopropenyl acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 9-16-29-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(=C)OC(=O)C
• Description: Isopropenyl acetate is a kind of organic compound, corresponding to the acetate ester of the enol tautomer of acetone. It appears as a clear, colorless liquid with a fruit-like odor. It has a moderate solubility in water and a low flash point. It has a lower density than water but heavier vapor than the air. It is widely used as an industrial and consumer based solvent. For example, it is used as the principal precursor to acetylacetone and some other important chemicals. It can also be used as a kind of food additive. Moreover, it is also applied to coatings, cleaning fluids and printing inks as well as used as cosmetic and personal care solvent and fragrance solvents. It has various kinds of advantages including being a good resin solvent, belonging to a Non-HAP (hazardous air pollutant solvent), having mild odor and undergoing fast evaporating. It is manufactured through treatment of acetone with ketene. However, it is highly flammable and of certain toxicity, therefore proper protective measures should be used during the operation.
• Uses: Reagent for acylation of potential enols. Iodine in isopropenyl acetate is a unique catalyst for the acetylation of a variety of alcohols, phenols and amines under solvent free conditions. It is used as a solvent for cellulose, plastics, oil and fats. It is also a building block used for various organic synthesis.

Technology Process of Isopropenyl acetate

There total 18 articles about Isopropenyl acetate 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: 99.5%

acetic acid (64-19-7,77671-22-8) + acetone (67-64-1) → Isopropenyl acetate (108-22-5)

Guidance literature:

acetic acid; In water; at 800 ℃;

acetone; In water; for 1h; Temperature;

Reference yield:

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + palladium diacetate (3375-31-3) → Isopropenyl acetate (108-22-5) + Allyl acetate (591-87-7) + 1-propenyl acetate (3249-50-1)

Guidance literature:

With p-benzoquinone; bis(triphenylphosphoranylidene)-ammonium acetate; In acetic acid; at 25 ℃; for 3h; under 760 Torr;

DOI:10.1016/S0022-328X(99)00521-5

Reference yield:

propene (187737-37-7,13987-01-4,15220-87-8,9003-07-0,676-63-1,25085-53-4) + acetic acid (64-19-7,77671-22-8) → Isopropenyl acetate (108-22-5) + Allyl acetate (591-87-7) + 2-hydroxypropyl acetate (627-69-0,82944-63-6) + 6-hydroxy-3-oxa-2-hexanone (36678-05-4) + propane-1,2-diol 2-monoacetate (6214-01-3) + (E)-1-propen-1-yl acetate (3249-50-1)

Guidance literature:

With bis(acetonitrile)chloronitropalladium(II); at 25 ℃; for 2h; Product distribution; various catalysts, times, O₂ atmosphere with 18O containing complex; further products;

DOI:10.1021/ja00298a024

upstream raw materials:

acetic acid

prop-1-yne

Ketene

acetone

Downstream raw materials:

N-Acetylimidazole

N-acetylpyrrolidinone

N-acetyl-2-piperidone

acetic acid-(2-methyl-1-methylen-allyl ester)

Refernces

• 1、 Van Beek, Hugo L.,Romero, Elvira,Fraaije, Marco W.. "Engineering cyclohexanone monooxygenase for the production of methyl propanoate". . p. 291 - 299. Retrieved 2017.
• 2、 Naylor. "-". . p. 244. Retrieved 1945.
• 3、 Allan et al.. "-". . p. 4700,4705. Retrieved 1957.
• 4、 Hering, Thea,Hari, Durga Prasad,Koenig, Burkhard. "Visible-light-mediated α-arylation of enol acetates using aryl diazonium salts". . p. 10347 - 10352. Retrieved 2013/01/15.