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14631-20-0

14631-20-0 Structure

14631-20-0 Structure
IdentificationMore
[Name]

N4-Acetylcytosine
[CAS]

14631-20-0
[Synonyms]

LABOTEST-BB LT00012625
N4-ACETYLCYTOSINE
N-ACETYLCYTOSINE
n-(1,2-dihydro-2-oxo-4-pyrimidinyl)-acetamid
4-Acetylamino-2-hydroxypyrimidine
N-Acetocytosine
N(4)-Acetylcytosine,98%
N-Actyl cytosine
N(sup 4)-acetylcytosine
4-(Acetylamino)pyrimidine-2(1H)-one
N-(2-Oxo-1,2-dihydropyrimidine-4-yl)acetamide
N-[(2-Oxo-1,2-dihydropyrimidine)-4-yl]acetamide
[EINECS(EC#)]

619-683-7
[Molecular Formula]

C6H7N3O2
[MDL Number]

MFCD00134466
[Molecular Weight]

153.14
[MOL File]

14631-20-0.mol
Questions And AnswerBack Directory
[Synthesis]

Acetic anhydride (2.1 mL, 22.05 mmol) was added to a solution of cytosine (500 mg) in pyridine (2.5 mL) under stirring. The mixture was stirred overnight at room temperature. The mixture was diluted with EtOAc (2.0 mL), and stirred again at room temperature for 30 minutes. The resulting white solid was filtered off, washed with EtOAc, and then dried under vacuum to obtain the product N4-acetylcytosine.

Synthetic Route of N4-acetylcytosine

Chemical PropertiesBack Directory
[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)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[HS Code ]

29335990
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[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.]
Spectrum DetailBack Directory
[Spectrum Detail]

N4-Acetylcytosine(14631-20-0)MS
N4-Acetylcytosine(14631-20-0)1HNMR
N4-Acetylcytosine(14631-20-0)IR1
N4-Acetylcytosine(14631-20-0)IR2
N4-Acetylcytosine(14631-20-0)Raman
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

N(4)-Acetylcytosine, 98%(14631-20-0)
[Sigma Aldrich]

14631-20-0(sigmaaldrich)
[TCI AMERICA]

N4-Acetylcytosine,>98.0%(T)(14631-20-0)
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