| Identification | More | [Name]
N4-Benzoylcytosine | [CAS]
26661-13-2 | [Synonyms]
LABOTEST-BB LT00138031
n-(2-oxo-1,2-dihydro-4-pyrimidinyl)benzamide
N-(2-Oxo-3H-pyrimidin-4-yl)benzamide
N4-BENZOYLCYTOSINE
N-Benzoylcytosine
4-BENZOYLCYTOSINE | [EINECS(EC#)]
628-907-2 | [Molecular Formula]
C11H9N3O2 | [MDL Number]
MFCD00239434 | [Molecular Weight]
215.21 | [MOL File]
26661-13-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
>300 °C (dec.) (lit.) | [density ]
1.33±0.1 g/cm3(Predicted) | [vapor pressure ]
0Pa at 25℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Aqueous Acid (Slightly, Heated), DMSO+DCl (Slightly, Heated) | [form ]
Solid | [pka]
7.75±0.10(Predicted) | [color ]
Off-White | [InChI]
InChI=1S/C11H9N3O2/c15-10(8-4-2-1-3-5-8)13-9-6-7-12-11(16)14-9/h1-7H,(H2,12,13,14,15,16) | [InChIKey]
XBDUZBHKKUFFRH-UHFFFAOYSA-N | [SMILES]
C(NC1=CC=NC(=O)N1)(=O)C1=CC=CC=C1 | [Surface tension]
72.2mN/m at 1g/L and 21.2℃ | [CAS DataBase Reference]
26661-13-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29335990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white crystalline powder | [Uses]
N4-Benzoylcytosine may be employed for the following syntheses:
- 3′-C-ethynyl and 3′-C-(1,4-disubstituted-1,2,3-triazolo) double-headed pyranonucleosides
- 2′-C-methyl-4′-thiocytidine, via the Pummerer reaction
- 2′-fluorinated L-nucleoside analogs
| [General Description]
N4-Benzoylcytosine is an amide and its anti-microbial activity against pathogenic microorganisms has been studied using the Disk Diffusion and the Pour Plate method. It can be synthesized via the condensation of benzoyl chloride with cytosine. | [Synthesis]
Under nitrogen protection, 100 L of acetonitrile was added to the reactor as a solvent, followed by 22 kg (196 mol) of 6-aminopyrimidin-2(1H)-one (anhydrous cytosine), 25 g of 4-dimethylaminopyridine (DMAP), and 24 kg of triethylamine as a base. After cooling the reaction mixture to 5-8°C, 34 kg of benzoyl chloride was slowly added dropwise. After the dropwise addition, the reaction mixture was allowed to warm up naturally to room temperature and stirred at 25°C for 1 hour. Subsequently, the reaction mixture was slowly heated to 40-45°C and kept at this temperature for 2 hours. Upon completion of the reaction, it was cooled to room temperature and press-filtered. About 60 L of acetonitrile filtrate was collected for recycling, and the filter cake was washed sequentially with water and ethanol, and dried to give 40 kg of a white solid product, N4-benzoylcytosine, which was analyzed by liquid chromatography to be 99.2% pure. | [References]
[1] Patent: US2011/245458, 2011, A1
[2] Chemical Communications, 2017, vol. 53, # 64, p. 8952 - 8955
[3] Heterocyclic Communications, 2007, vol. 13, # 4, p. 251 - 256
[4] Russian Journal of Organic Chemistry, 2008, vol. 44, # 3, p. 358 - 361
[5] Journal of the Chemical Society, 1956, p. 2388,2392 |
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