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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:
1538-75-6
Peso molecular:
186.25
Beilstein/REAXYS Number:
386552
EC Number:
216-263-1
MDL number:
MFCD00008842
UNSPSC Code:
12352100
PubChem Substance ID:
24848589
NACRES:
NA.22

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

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

681059

2-Methyl-6-nitrobenzoic anhydride

1-Naphthyl phosphate 99%

Sigma-Aldrich

N5602

1-Naphthyl phosphate

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
Bulletin of the Chemical Society of Japan, 67, 210-210 (1994)
Australian Journal of Chemistry, 60, 75-75 (2007)
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
Q Zhu et al.
Bioorganic & medicinal chemistry letters, 11(9), 1105-1107 (2001-05-17)
Commercially available 'fast-deprotecting' phosphoramidites are useful for synthesizing oligonucleotides containing alkali-sensitive nucleotides. However, N-acetylated oligonucleotides were observed during solid-phase synthesis using 'fast-deprotecting' phosphoramidites in conjunction with K2CO3/MeOH ('ultra-mild') deprotection. Transamidation was localized at deoxyguanosine, which is protected as its isopropylphenoxyacetyl
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