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157864

Sigma-Aldrich

1-Acetylimidazole

98%

Synonym(s):

1-(1H-Imidazol-1-yl)ethan-1-one, 1-(1H-Imidazol-1-yl)ethanone, 1-Acetyl-1H-imidazole, N-Acetylimidazole

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About This Item

Empirical Formula (Hill Notation):
C5H6N2O
CAS Number:
2466-76-4
Molecular Weight:
110.11
Beilstein/REAXYS Number:
108425
EC Number:
219-577-7
MDL number:
MFCD00005287
UNSPSC Code:
12352005
PubChem Substance ID:
24849704
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

mp

99-105 °C (lit.)

solubility

water: soluble 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

CC(=O)n1ccnc1

InChI

1S/C5H6N2O/c1-5(8)7-3-2-6-4-7/h2-4H,1H3

InChI key

VIHYIVKEECZGOU-UHFFFAOYSA-N

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General description

Rate of solvolysis of 1-acetylimidazole in acid solutions was evaluated. Reaction of 1-acetylimidazole with orthophosphate and adenosine-5′-phosphate has been reported.

Application

1-Acetylimidazole was used as acetylation reagent for amino groups. It was also employed for acetylation of histones.
Relatively specific reagent for tyrosyl residue acetylation. Reagent used in the synthesis of annulated imidazole derivatives.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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I Wells et al.
Biochemistry, 31(40), 9520-9525 (1992-10-13)
Treatment of prostaglandin endoperoxide (PGH) synthase apoprotein with a 100- or 1000-fold excess of N-acetylimidazole (NAI) led to time-dependent inactivation of both cyclooxygenase and peroxide activities. Reconstitution of apoprotein with heme prior to incubation with NAI substantially protected the enzyme
Chemische Berichte, 125, 1939-1939 (1992)
The Solvolysis of 1-Acetylimidazole in Concentrated Acid and Salt Solutions.
Marburg S and Jencks WP.
Journal of the American Chemical Society, 84(2), 232-239 (1962)
Variation of the nuclear, subnuclear and chromosomal flavanol deposition in hemlock and rye.
Feucht W, et al.
International Journal of Molecular Sciences, 8(7), 635-650 (2007)
Hong Xu et al.
Protein and peptide letters, 10(5), 503-509 (2003-10-17)
Cinnamomin is a type II ribosome-inactivating protein (RIP) and its A-chain (CTA) is a RNA N-glycosidase. It is observed that modification of tyrosine residues by N-acetylimidazole (N-AI) causes almost complete loss of CTA activity. Adenine partially protects tyrosine residues from
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