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N4-Acetylcytosine

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N4-Acetylcytosine Basic information

Product Name:
N4-Acetylcytosine
Synonyms:
  • n-(1,2-dihydro-2-oxo-4-pyrimidinyl)-acetamid
  • N-ACETYLCYTOSINE
  • N4-ACETYLCYTOSINE
  • LABOTEST-BB LT00012625
  • 4-Acetylamino-2-hydroxypyrimidine
  • N-Acetocytosine
  • N(4)-Acetylcytosine,98%
  • N-Actyl cytosine
CAS:
14631-20-0
MF:
C6H7N3O2
MW:
153.14
EINECS:
619-683-7
Product Categories:
  • Heterocyclic Compounds
  • Building Blocks
  • Biochemistry
  • Nucleobases and their analogs
  • Heterocyclic Building Blocks
  • Pyrimidines
  • Nucleosides, Nucleotides & Related Reagents
Mol File:
14631-20-0.mol
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N4-Acetylcytosine Chemical Properties

Melting point:
>300 °C (lit.)
Density 
1.41±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO (Sparingly), Methanol (Very Slightly)
form 
Solid
pka
7.60±0.10(Predicted)
color 
Off-White to Pale Beige
BRN 
138451
InChI
InChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChIKey
IJCKBIINTQEGLY-UHFFFAOYSA-N
SMILES
C(NC1=CC=NC(=O)N1)(=O)C
CAS DataBase Reference
14631-20-0(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-37/39-26-37
WGK Germany 
3
HS Code 
29335995

MSDS

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N4-Acetylcytosine Usage And Synthesis

Chemical Properties

Crstalline powder

Uses

N4-Acetylcytosine may be used in the preparation of cytidine. It may be used in the preparation of 1-(4-azido-4-deoxy-β-D-glucopyranosyl)cytosine.

Definition

ChEBI: N(4)-acetylcytosine is a pyrimidone that is cytosine bearing an N(4)-acetyl substituent. It is a pyrimidone, a nucleobase analogue and a member of acetamides. It is functionally related to a cytosine.

General Description

Four stable conformers of N4-acetylcytosine, and the one of the stable form containing an intramoleuclar six-membered ring have been reported by theoretical calculations.The infrared and FT-Raman spectra of N4-acetylcytosine in the solid phase has been reported.

Purification Methods

If TLC or paper chromatography shows that it contains unacetylated cytosine, then reflux it in Ac2O for 4hours, cool at 3-4o for a few days, collect the crystals, wash them with cold H2O, then EtOH and dry at 100o. It is insoluble in EtOH and dissolves in H2O with difficulty, but crystallises in prisms from hot H2O. It is hydrolysed by 80% aqueous AcOH at 100o/1hour. [UV: Brown et al. J Chem Soc 2384 1956, Codington et al. J Am Chem Soc 80 5164 1958.] It forms an Hg salt [Fox et al. J Am Chem Soc 79 5060 1957]. [Beilstein 25 III/IV 3657.]

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