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143502

Sigma-Aldrich

Trimethylacetic anhydride

99%

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Synonym(s):
Pivalic anhydride, 2,2-Dimethylpropionic anhydride
Linear Formula:
[(CH3)3CCO]2O
CAS Number:
1538-75-6
Molecular Weight:
186.25
Beilstein:
386552
EC Number:
216-263-1
MDL number:
MFCD00008842
UNSPSC Code:
12352100
PubChem Substance ID:
24848589
NACRES:
NA.22

Quality Level

200

Assay

99%

form

liquid

refractive index

n20/D 1.409 (lit.)

bp

193 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

SMILES string

CC(C)(C)C(=O)OC(=O)C(C)(C)C

InChI

1S/C10H18O3/c1-9(2,3)7(11)13-8(12)10(4,5)6/h1-6H3

InChI key

PGZVFRAEAAXREB-UHFFFAOYSA-N

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Application

Acylation and esterification reagent for anilines and phenols, respectively.
Trimethylacetic anhydride was used:
  • in solid-phase oligonucleotide synthesis
  • in kinetic resolution of racemic 2-hydroxy-γ-butyrolactones with diphenylacetic acid
  • as acylation and esterification reagent for anilines
  • as acylation and esterification reagent for phenols

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H317,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Australian Journal of Chemistry, 60, 75-75 (2007)
Bulletin of the Chemical Society of Japan, 67, 210-210 (1994)
Pharmacological Research, 10, 68-68 (1993)
Z J Kamiński
International journal of peptide and protein research, 43(3), 312-319 (1994-03-01)
According to the concept presented, esters forming an amide (peptide) bond by the mechanism SN#DN or SN#*DN involving fast decay of the tetrahedral intermediate may behave as 'superactive acylating reagents'. These should render coupling involving less reactive substrates, i.e. sterically
Marco Jost et al.
The Journal of biological chemistry, 290(45), 26882-26898 (2015-09-01)
Acyl-CoA mutases are a growing class of adenosylcobalamin-dependent radical enzymes that perform challenging carbon skeleton rearrangements in primary and secondary metabolism. Members of this class of enzymes must precisely control substrate positioning to prevent oxidative interception of radical intermediates during
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