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CAS RN: 108-05-4 | Product Number: A0045

Vinyl Acetate Monomer (stabilized with NaOH)


Purity: >99.0%(GC)
Synonyms:
  • Acetic Acid Vinyl Ester Monomer (stabilized with NaOH)
Documents:
500ML
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Product Number A0045
Purity / Analysis Method >99.0%(GC)
Molecular Formula / Molecular Weight C__4H__6O__2 = 86.09  
Physical State (20 deg.C) Liquid
Condition to Avoid Light Sensitive,Air Sensitive
CAS RN 108-05-4
Reaxys Registry Number 1209327
PubChem Substance ID 87561748
SDBS (AIST Spectral DB) 1299
Merck Index (14) 9992
MDL Number

MFCD00008713

Specifications
Appearance Colorless clear liquid
Purity(GC) min. 99.0 %
Properties (reference)
Melting Point -93 °C
Boiling Point 72 °C
Flash point -8 °C
Specific Gravity (20/20) 0.93
Refractive Index 1.40
Solubility in water Slightly soluble
Degree of solubility in water 25 g/l   20 °C
Solubility (miscible with) Alcohol,Ether
Solubility (soluble in) Chloroform,Acetone
GHS
Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H332 : Harmful if inhaled.
H319 : Causes serious eye irritation.
H373 : May cause damage to organs through prolonged or repeated exposure.
H341 : Suspected of causing genetic defects.
H351 : Suspected of causing cancer.
H335 : May cause respiratory irritation.
H225 : Highly flammable liquid and vapour.
Precautionary Statements P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P233 : Keep container tightly closed.
P201 : Obtain special instructions before use.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
Related Laws:
EC Number 203-545-4
RTECS# AK0875000
Transport Information:
UN Number UN1301
Class 3
Packing Group II
HS Number 2915320000
Application
Acetylation of Alcohols via Biotransformation using Acetylating Reagents

References

1)Regioselective Lipase-catalyzed Acylation of 4,6-O-benzylidene-α-and-β-D-pyranoside Derivatives Displaying a Range of Anomeric Substituents

J. J. Gridley, A. J. Hacking, H. M. I. Osborn, D. G. Spackman, Synlett 1997, 1397.

2)On the Regioselective Acylation of 1,6-Anhydro-β-D-and L-Hexopyranoses Catalyzed by Lipases: Structural Basis and Synthetic Applications

N. Boissiere-Junot, C. Tellier, C. Rabiller, J. Carbohydr. Chem. 1998, 17, 99.

3)Regioselective Acylation of Polyhydroxylated Natural Compounds Catalyzed by Candida Antarctica Lipase B (Novozym 435) in Organic Solvents

B. Danieli, M. Luisetti, G. Sampognaro, G. Carrea, S. Riva, J. Mol. Catal. B: Enzymatic, 1997, 3, 193.

4)Protection for the Hydroxyl Group, Including 1,2-and 1,3-Diols

P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


Application
Acetylation of Alcohols via Transesterification using Acetylating Reagents

References

1)Acylation of Alcohols and Amines with Vinyl Acetates Catalyzed by Cp*2Sm(thf)2

Y. Ishii, M. Takeno, Y. Kawasaki, A. Muromachi, Y. Nishiyama, S. Sakaguchi, J. Org. Chem. 1996, 61, 3088.

2)Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols

P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


Application
Acetylation of Alcohols using Acetylating Reagents and Acid Catalysts

References

1)Molecular Iodine Catalyzed Selective Acetylation of Alcohols with Vinyl Acetate

J. W. J. Bosco, A. Agrahari, A. K. Saikia, Tetrahedron Lett. 2006, 47, 4065.

2)Molecular Iodine in Isopropenyl Acetate (IPA): A Highly Efficient Catalyst for the Acetylation of Alcohols, Amines and Phenols under Solvent Free Conditions

N. Ahmed, J. E. van Lier, Tetrahedron Lett. 2006, 47, 5345.

3)Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols

P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


Application
Rhodium-Catalyzed Cross-coupling of Organoboron Compounds with Vinyl Acetate

Typical procedure: Under nitrogen atmosphere, a mixture of an arylboron compounds (0.50 mmol), [RhCl(cod)]2 (6.2 mg, 13 µmol), DPPB (11.7 mg, 28 µmol), and K3PO4 (320 mg, 1.5 mmol) is diluted with toluene (2.0 mL). Alkenyl acetate (1.1 or 2.5 mmol) and tert-amyl alcohol (0.55-1.5 mmol) are added into the resulting suspension at room temperature. The mixture is stirred at 100℃ for 24 h and then diluted with hexane (2.0 mL) or EtOAc (2.0 mL). After the filtration through a Celite pad, solvent is removed from the filtrate under reduced pressure. The residue is purified with a flash column chromatography (EtOAc-hexane) to give the desired product.

References


PubMed Literature


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