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1538-75-6 - Trimethylacetic anhydride, 99% - Pivalic anhydride - B22983 - Alfa Aesar

B22983 Trimethylacetic anhydride, 99%

CAS Number
1538-75-6
Synonyms
Pivalic anhydride

Size Price ($) Quantity Availability
25g 41.58
100g 117.60
500g 528.30
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Trimethylacetic anhydride, 99%

MDL
MFCD00008842
EINECS
216-263-1

Chemical Properties

Formula
C10H18O3
Formula Weight
186.25
Boiling Point
193°
Flash Point
63°(145°F)
Density
0.918
Refractive Index
1.4090
Sensitivity
Moisture Sensitive
Solubility
Miscible with acetonitrile.

Applications

Trimethylacetic anhydride is used as acylation and esterification reagents. It is involved in acylation and esterification reactions with anilines and phenols. It is also used in solid-phase oligonucleotide synthesis and in the kinetic resolution of racemic 2-hydroxy-gamma-butyrolactones with diphenylacetic acid. It is also employed in the production of cyano-4, N-tert-butyloxycarbonyl piperidine.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents, strong acids, strong bases and strong reducing agents.

Literature References

The direct hydrogenation of carboxylic acids to aldehydes has been achieved in the presence of pivalic anhydride and Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548 : Chem. Lett., 1143 (1998).

Alcohols can be protected as their pivaloyl (Pv) esters by reaction with the anhydride in the presence of MgBr2 - Et3N or Sc(OTf)3 in acetonitrile: J. Org. Chem., 61, 5702 (1996). See also Trimethyl­acetyl­ chloride, A15051 .

Zhu, J. L.; Liu, Y.; Liu, X. Y.; Liu, H. J.; Chen, Y. Multi stimuli-responsive photoluminescent nanocomposite of silver nanoclusters with hyperbranched polyethylenimine derivatives. RSC Adv. 2015, 5 (11), 8146-8151.

Wu, J.; Leng, W. L.; Liao, H.; Hoang, K. L. M.; Le, K.; Liu, X. W. Intramolecular C-N Bond Formation under Metal-free Conditions: Synthesis of Indolizines. Chem. Asian J. 2015, 10 (4), 853-856.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H227

Causes severe skin burns and eye damage. Causes serious eye damage. Combustible liquid.

Precautionary Statements: P280-P305+P351+P338-P309-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
386552
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2915.90
TSCA
Yes

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