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14631-20-0

Basic Information
CAS No.: 14631-20-0
Name: N4-Acetylcytosine
Article Data: 29
Molecular Structure:
Molecular Structure of 14631-20-0 (N4-Acetylcytosine)
Formula: C6H7N3O2
Molecular Weight: 153.14
Synonyms: Acetamide,N-(1,2-dihydro-2-oxo-4-pyrimidinyl)- (8CI,9CI);Cytosine, N-acetyl- (6CI);2(1H)-Pyrimidinone, 4-(acetylamino)-;4-N-Acetylcytosine;N-Acetylcytosine;Acetamide,N-(2,3-dihydro-2-oxo-4-pyrimidinyl)-;NSC 210403;
EINECS: 619-683-7
Density: 1.41 g/cm3
Melting Point: >300 °C(lit.)
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-37/39-26
PSA: 75.11000
LogP: 0.21360
Synthetic route
71-30-7

Cytosine

108-24-7

acetic anhydride

14631-20-0

4-N-Acetylcytosine

Conditions
ConditionsYield
With phosphoric acid at 100℃; for 8h;98%
With pyridine for 2.5h; Heating;97.2%
With pyridine at 20℃; for 24h;85%
32830-01-6

4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one

A

14631-20-0

4-N-Acetylcytosine

B

84856-79-1

4-Acetamido-1-(2,3-di-O-acetyl-5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one

C

58538-06-0

4-Amino-1-(5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one

Conditions
ConditionsYield
With hydrogen bromide In N,N-dimethyl-formamide at 120℃; for 0.416667h;A 20%
B 3%
C 45%
3768-18-1

N-acetylcytidine

A

14631-20-0

4-N-Acetylcytosine

B

120885-66-7

N4,O5'-diacetyl-2',3'-dideoxycytidine

C

126430-20-4

N4-acetyl-5'-O-(acetoxyisobutyryl)-2',3'-dideoxycytidine

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
40094-20-0

N4-acetyl-O5'-trityl-2'deoxy-cytidine

A

14631-20-0

4-N-Acetylcytosine

B

65475-52-7

4,5-dihydro-5-trityloxymethylfuran-4-one

Conditions
ConditionsYield
With pyridine; chromium(VI) oxide; acetic anhydride In dichloromethane Ambient temperature; 45 - 60 min;
4-acetylamino-1H-<2-14C>pyrimidin-2-one

4-acetylamino-1H-<2-14C>pyrimidin-2-one

14631-20-0

4-N-Acetylcytosine

71-30-7

Cytosine

75-36-5

acetyl chloride

14631-20-0

4-N-Acetylcytosine

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; Inert atmosphere;
14631-20-0

4-N-Acetylcytosine

Me3SiX

Me3SiX

54230-57-8

N4-acetyl-O-trimethylsilylcytosine

Conditions
ConditionsYield
100%
14631-20-0

4-N-Acetylcytosine

6798-35-2

N-(1,2,2,2-tetrachloroethyl)benzamide

136506-88-2

N-[1-(4-Acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2,2-trichloro-ethyl]-benzamide

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 0℃; for 0.5h;99%
14631-20-0

4-N-Acetylcytosine

293751-03-8

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

293751-17-4

(2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate

Conditions
ConditionsYield
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Reflux;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 5.5h; Reflux; Inert atmosphere;
96%
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Heating;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 3h; Heating; Further stages.;
82%
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile82%
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 40℃; for 0.333333h;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 2.5h; Heating / reflux;
60%
14631-20-0

4-N-Acetylcytosine

147027-09-6

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate

147126-78-1

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[4-(methylcarboxamido)-2-oxo-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With triethylsilane; iodine In dichloromethane at 0℃; for 1h; Inert atmosphere;
Stage #2: 4-N-Acetylcytosine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction;
95%
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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)-Acetylcy

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Chemistry

Molecule structure of N4-Acetylcytosine (CAS NO.14631-20-0):

IUPAC Name: N-(2-Oxo-1H-pyrimidin-6-yl)acetamide 
Molecular Weight: 153.13868 g/mol
Molecular Formula: C6H7N3O2 
Density: 1.41 g/cm3 
Melting Point: >300 °C(lit.)
Index of Refraction: 1.625
Molar Refractivity: 38.32 cm3
Molar Volume: 108.3 cm3
Surface Tension: 54.4 dyne/cm
XLogP3: -2.4
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Tautomer Count: 9
Exact Mass: 153.053826
MonoIsotopic Mass: 153.053826
Topological Polar Surface Area: 70.6
Heavy Atom Count: 11
Canonical SMILES: CC(=O)NC1=CC=NC(=O)N1
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
Product Categories of N4-Acetylcytosine (CAS NO.14631-20-0): Heterocyclic Compounds; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Building Blocks; Heterocyclic Building Blocks; Pyrimidines

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26 
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

Specification

 N4-Acetylcytosine (CAS NO.14631-20-0) is also named as Acetamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)- ; N-(2-Oxo-1,2-dihydro-4-pyrimidinyl)acetamide ; N-(2-Oxo-1,2-dihydropyrimidin-4-yl)acetamid ; N-Acetylcytosine .