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Merck
CN

143502

Trimethylacetic anhydride

99%

Synonym(s):

Pivalic anhydride, 2,2-Dimethylpropionic anhydride

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About This Item

Linear Formula:
[(CH3)3CCO]2O
CAS Number:
1538-75-6
Molecular Weight:
186.25
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24848589
EC Number:
216-263-1
Beilstein/REAXYS Number:
386552
MDL number:
MFCD00008842
Assay:
99%
Form:
liquid

Key Documents

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InChI key

PGZVFRAEAAXREB-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

99%

form

liquid

Quality Level

200

bp

193 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

functional group

anhydride, ester

Related Categories

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

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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCV5826
MKCW6929
MKCQ4396
MKCP0427
MKCN7943

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Australian Journal of Chemistry, 60, 75-75 (2007)
Bulletin of the Chemical Society of Japan, 67, 210-210 (1994)
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
Pharmacological Research, 10, 68-68 (1993)
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