| Identification | Back Directory | [Name]
(4-Methylphenyl)sulfonyl acetate | [CAS]
26908-82-7 | [Synonyms]
acetyl p-toluenesulfonate
UOAJUPONZOXFNX-UHFFFAOYSA-N
(4-METHYLPHENYL)SULFONYL ACETATE
(4-Methylbenzene)sulfonyl Acetate
Acetic P-Toluenesulfonic Anhydride
Acetic Acid, Anhydride With P-Toluenesulfonic Acid
Acetic acid, anhydride with 4-methylbenzenesulfonic acid | [Molecular Formula]
C9H10O4S | [MOL File]
26908-82-7.mol | [Molecular Weight]
214.24 |
| Chemical Properties | Back Directory | [Melting point ]
54-56 °C | [Boiling point ]
325.7±35.0 °C(Predicted) | [density ]
1.279±0.06 g/cm3(Predicted) | [solubility ]
sol acetonitrile, dichloromethane, toluene | [form ]
crystals | [color ]
colorless |
| Hazard Information | Back Directory | [Preparation]
(4-Methylphenyl)sulfonyl acetate prepared from Acetyl Chloride and
p-Toluenesulfonic Acid[1]. | [storage]
the solid is readily hydrolyzed, so it must be protected from contact
with moisture; thermal decomposition is also possible. | [Purification Methods]
The most likely impurity is p-toluenesulfonic acid (could be up to 10%). This can be removed by dissolving it in dry Et2O and cooling until the anhydride crystallises out. It decomposes on heating; below ~130o it gives the disulfonic anhydride and above ~130o polymers are formed, but it can be distilled in a vacuum if it is free of acid. It is used for cleaving ethers [Prep, IR, NMR: Karger & Mazur J Org Chem 36 528, Karger & Mazur J Org Chem 36 532 1971]. [Beilstein 11 III 255.] | [References]
[1]. (a) Karger, M. H.; Mazur, Y. JOC 1971, 36, 528. (b) Lin, J. S.; Sleezer, P. D. U.S. Patent 4 219 495, 1980.
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