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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:
108425
EC Number:
219-577-7
MDL number:
MFCD00005287
UNSPSC Code:
12352005
PubChem Substance ID:
24849704
NACRES:
NA.22

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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The Reaction of 1-Acetylimidazole with Orthophosphate*.
Brinigar WS and Knaff DB.
Biochemistry, 4(3), 406-409 (1965)
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)
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)
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)
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