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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
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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.[1] Reaction of 1-acetylimidazole with orthophosphate and adenosine-5′-phosphate has been reported.[2]

Application

1-Acetylimidazole was used as acetylation reagent for amino groups. It was also employed for acetylation of histones.[3]
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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0543
MKCT0958
MKCT6300
MKCT6299
MKCT6298

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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)
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)
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