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Merck

143502

Sigma-Aldrich

Trimethylacetic anhydride

99%

Sinónimos:

Pivalic anhydride, 2,2-Dimethylpropionic anhydride

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About This Item

Fórmula lineal:
[(CH3)3CCO]2O
Número de CAS:
Peso molecular:
186.25
Beilstein/REAXYS Number:
386552
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

liquid

refractive index

n20/D 1.409 (lit.)

bp

193 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

functional group

anhydride
ester

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

162.5 °F - closed cup

flash_point_c

72.5 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Pharmacological Research, 10, 68-68 (1993)
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
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
Australian Journal of Chemistry, 60, 75-75 (2007)
Alexey Evdokimov et al.
Nucleic acids research, 41(12), e123-e123 (2013-04-24)
DNA probes for the studies of damaged strand excision during the nucleotide excision repair (NER) have been designed using the novel non-nucleosidic phosphoramidite reagents that contain N-[6-(9-antracenylcarbamoyl)hexanoyl]-3-amino-1,2-propandiol (nAnt) and N-[6-(5(6)-fluoresceinylcarbamoyl)hexanoyl]-3-amino-1,2-propandiol (nFlu) moieties. New lesion-imitating adducts being inserted into DNA show

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