N4-Acetylcytosine

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
N4-Acetylcytosine Structure
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
pka7.60±0.10(Predicted)
color Off-White to Pale Beige
BRN 138451
InChIInChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChIKeyIJCKBIINTQEGLY-UHFFFAOYSA-N
SMILESC(NC1=CC=NC(=O)N1)(=O)C
CAS DataBase Reference14631-20-0(CAS DataBase Reference)
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 Information
ProviderLanguage
SigmaAldrich English
ALFA English
N4-Acetylcytosine Usage And Synthesis
Chemical PropertiesCrstalline powder
UsesN4-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.
DefinitionChEBI: 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 DescriptionFour 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 MethodsIf 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.]
N4-Acetylcytosine Preparation Products And Raw materials
Preparation Products4-Amino-1-(2-deoxy-2,2-difluoro-a-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone Hydrochloride
N4-BENZOYL-5-METHYLDEOXYCYTIDINE N4-Acetylcytidine IBU-DEOXYCYTIDINE N4-ANISOYL-2'-DEOXYCYTIDINE N-Benzoyl-2'-deoxy-cytidine N4-ANISOYLCYTIDINE DMT-DCYTIDINE (N6-BENZOYL) CYANOETHYL PHOSPHORAMIDITE) 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-BENZOYL-5-METHYL-2'-DEOXYCYTIDINE N4-ACETYL-2'-DEOXYCYTIDINE N4-Acetylcytosine 5-BROMO-DC CEP 5'-DIMETHOXYTRITYL-N4-BENZOYL-2'-DEOXYCYTIDINE-3'-(METHYL-N,N-DIISOPROPYL)PHOSPHORAMIDITE N-blocked-5'-O-DMT-2'-O-TBDMS CED cytidine phosphoramidite 5'-O-Dimethoxytrityl-N-benzoyl-desoxycytidine N4,3'-O-DIBENZOYL-2'-DEOXYCYTIDINE N4-Benzoylcytidine 5'-O-DMT-N4-Benzoyl-2'-deoxycytidine 3'-CE phosphoramidite 5'-O-(4,4'-DIMETHOXYTRITYL)-N4-ISOBUTYRYL-2'-DEOXYCYTIDINE

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