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Transcript
Acetic anhydride
Product Number A6404
Store at Room Temperature
Product Description
Molecular Formula: C4 H6O3
Molecular Weight: 102.1
CAS Number: 108-24-7
1
Boiling Point: 139 °C
1
Density: 1.082 g/ml
Molarity: 10.6 M (calculated from density and
molecular weight)
1
Synonyms: acetic oxide, acetyl oxide
Acetic anhydride is a reagent that is used in the
manufacturing of acetyl compounds and cellulose
acetates. It is also utilized as a solvent in the
examination of wool fat, glycerol, fatty and volatile oils,
1
and resins. In the synthesis of organic compounds,
acetic anhydride is used in various reactions, including
the cleavage of dialkyl ethers, the formation of
anhydrides from carboxylic acids, the addition of
methylthiomethyl groups to phenol rings, and the
addition of acyl and acyloxy groups across double
bonds. Acetic anhydride will also react with such
2
acetals, alcohols, and sulfoxides.
A wide variety of substrates and materials has been
synthesized using acetic anhydride. Small molecule
syntheses include the preparation of substituted
2-pyridones, acylated silyl ketene acetals, and
estrogen receptor ligands derived from
3,4,5
2,3-diarylpiperazines.
Larger materials which have
been prepared with acetic anhydride include cellulose
and poly(ethylene oxide)-block-poly(N-hexyl-L6,7
aspartamide)-acyl conjugates.
Acetic anhydride has been used to hyperacetylate
histones to investigate transcriptional effects of the
NAD-dependent histone deacetylase Sir2 in
Drosophila on a complex of the hyperacetylated
8
histones with DNA. An affinity chromatography/mass
spectrometry method for the analysis of
neuroendocrine peptides from carboxypeptidase E
9
deficient mice has been reported.
A microarray of oligonucleotide probes linked to a solid
support that uses acetic anhydride in the preparation
10
has been described. Acetic anhydride is utilized in
an assay of a fluorescently labeled peptide catalyst
library for application to the resolution of secondary
11
alcohols.
Precautions and Disclaimer
For Laboratory Use Only. Not for drug, household or
other uses.
Preparation Instructions
This product is miscible in chloroform and ether. In
alcohol, this product will form ethyl acetate. In water
(0.1 ml/ml, v/v), this product will slowly form acetic
1
acid.
References
1. The Merck Index, 12th ed., Entry# 53.
2. Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure, 4th ed., March,
J., John Wiley & Sons (New York, NY: 1992),
pp. 600, 822, 1173.
3. Padwa, A., et al., Synthesis of substituted
2-pyridones via the pummerer cyclizationdeprotonation-cycloaddition cascade of
imidosulfoxides. J. Org. Chem., 64(6), 2038-2049
(1999).
4. Mermerian, A. H., and Fu, G. C., Catalytic
enantioselective synthesis of quaternary
stereocenters via intermolecular C-acylation of
silyl ketene acetals: dual activation of the
electrophile and the nucleophile. J. Am. Chem.
Soc., 125(14), 4050-4051 (2003).
5. Gust, R., et al., Synthesis, structural evaluation,
and estrogen receptor interaction of 2,3diarylpiperazines. J. Med. Chem., 45(11),
2325-2337 (2002).
6. Chauvelon, G., et al., Preparation of sulfoacetate
derivatives of cellulose by direct esterification.
Carbohydr. Res., 338(8), 743-750 (2003).
7.
8.
9.
Adams, M. L., and Kwon, G. S., The effects of acyl
chain length on the micelle properties of
poly(ethylene oxide)-block-poly(N-hexyl-Laspartamide)-acyl conjugates. J. Biomater. Sci.
Polym. Ed., 13(9), 991-1006 (2002).
Parsons, X. H., et al., Histone deacetylation by
Sir2 generates a transcriptionally repressed
nucleoprotein complex. Proc. Natl. Acad. Sci.
USA, 100(4), 1609-1614 (2003).
Che, F. Y., and Fricker, L. D., Quantitation of
fat
fat
neuropeptides in Cpe /Cpe mice using
differential isotopic tags and mass spectrometry.
Anal. Chem., 74(13), 3190-3198 (2002).
10. Belosludtsev, Y., et al., DNA microarrays based on
noncovalent oligonucleotide attachment and
hybridization in two dimensions. Anal. Biochem.,
292(2), 250-256 (2001).
11. Copeland, G. T., and Miller, S. J., Selection of
enantioselective acyl transfer catalysts from a
pooled peptide library through a fluorescencebased activity assay: an approach to kinetic
resolution of secondary alcohols of broad
structural scope. J. Am. Chem. Soc., 123(27),
6496-6502 (2001).
GCY / RXR 5/06
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