• Chemical structure of N3-Benzoyluracil (3-benzoyluracil), CAS 2775-87-3, 98% — N3-benzoyl-protected uracil, a base-labile building block for nucleoside and oligonucleotide synthesis. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
  • ¹H NMR spectrum of N3-Benzoyluracil (CAS 2775-87-3) acquired in DMSO-d₆ at 298.1 K on a Bruker Avance 400.15 MHz spectrometer with a 10 s relaxation delay for accurate integration. Spectrum shows the uracil N–H at ~11.4 ppm (0.96 integration), three aromatic Ar–H multiplets between ~7.5–8.0 ppm (2.02 + 1.04 + 2.00 integration, benzoyl + ring), and the uracil C–H at ~5.7 ppm (1.00 integration), confirming structure and ≥98% purity. Batch NOR2775873-25-2, analysed 15 August 2025 by NorrChemica.​​​​​​​​​​​​​​​
  • ¹³C NMR spectrum of N3-Benzoyluracil (CAS 2775-87-3) acquired in DMSO-d₆ at 298.1 K on a Bruker Avance 100.63 MHz spectrometer with a 2 s relaxation delay and 2048 scans. Spectrum shows the two carbonyl C=O signals at 170.0 and 162.9 ppm (benzoyl and uracil C2/C4), aromatic Cₐᵣ resonances at 150.1, 143.3, 135.4, 131.3, 130.2 and 129.5 ppm (phenyl + uracil C6), and the uracil C–H at 100.1 ppm, consistent with the proposed structure and ≥98% purity. Batch NOR2775873-25-2, analysed 15 August 2025 by NorrChemic
  • gHSQC 2D NMR spectrum of N3-Benzoyluracil (CAS 2775-87-3) acquired in DMSO-d₆ on a Bruker Avance spectrometer, correlating ¹H (F2, ~2–8.5 ppm) with ¹³C (F1, ~30–150 ppm) one-bond couplings. Cross-peaks in the aromatic region (~7.5–8.0 ppm / ~129–135 ppm) confirm the benzoyl and uracil C–H assignments, and the cross-peak at ~5.7 ppm / ~100 ppm corresponds to the uracil C5–H, consistent with the proposed N3-benzoyluracil structure. Batch NOR2775873-25-2, analysed by NorrChemica.​​​​​​​​​​​​​​​​
  • gHMBC 2D NMR spectrum of N3-Benzoyluracil (CAS 2775-87-3) in DMSO-d₆, Bruker Avance, correlating ¹H (F2, ~2–12 ppm) with ¹³C (F1, ~30–190 ppm) through long-range (²J, ³J) couplings. Cross-peaks from the aromatic protons (~7.5–8.0 ppm) to the carbonyl carbons at ~170 and ~163 ppm confirm connectivity between the benzoyl group and the uracil N3 position; correlations from C5–H (~5.7 ppm) and C6–H (~7.7 ppm) to ring carbons establish the full N3-acylated uracil framework. NorrChemica.
  • gCOSY 2D NMR spectrum of N3-Benzoyluracil (CAS 2775-87-3) in DMSO-d₆, Bruker Avance, showing homonuclear ¹H–¹H scalar (²J, ³J) correlations across both F1 and F2 (~2.5–12 ppm). Diagonal peaks reproduce the 1D ¹H spectrum; off-diagonal cross-peaks confirm coupling between the uracil C5–H (~5.7 ppm) and C6–H (~7.7 ppm), and ortho/meta/para couplings within the benzoyl aromatic system (~7.5–8.0 ppm). N–H at ~11.4 ppm shows no scalar coupling cross-peak. NorrChemica.
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NorrChemica™

N3-Benzoyluracil

CAS 2775-87-3 ≥98%

N3-Benzoyluracil | CAS 2775-87-3 | ≥98%

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Technical Specifications

CAS Number 2775-87-3
MDL Number MFCD00525660
SMILES C1=CC=C(C=C1)C(=O)N2C(=O)C=CNC2=O
InChI InChI=1S/C11H8N2O3/c14-9-6-7-12-11(16)13(9)10(15)8-4-2-1-3-5-8/h1-7H,(H,12,16)
InChIKey RJAJHSYADHZMNA-UHFFFAOYSA-N
PubChem CID 569513
Molecular Formula C₁₁H₈N₂O₃
Molecular Weight 216.19 g/mol
Melting Point 214-217 °C
Solubility Soluble in DMF, acetonitrile, and DMSO; limited solubility in water
Purity ≥98%
Physical Form White to off-white crystalline powder
HS Code 2933.59
Shelf Life Retest period: 36 months from date of manufacture
Storage Conditions Store at room temperature in a tightly sealed container, protected from moisture

Product Description & Scientific Applications

N3-Benzoyluracil (3-benzoyl-1H-pyrimidine-2,4-dione) is uracil with the N3 imide protected as a benzamide. The benzoyl makes the ring electron-poor and, by blocking N3, directs functionalisation to the free N1. It is the pyrimidine counterpart to N3-benzoylthymine for parallel methodology development across the uracil and thymine series, and is observably more base-labile than N3-benzoylthymine under matched deprotection conditions.

Mitsunobu coupling. As an N1 pronucleophile it couples to primary and secondary alcohols with inversion, building carbocyclic and acyclic uracil nucleoside analogues. N1 versus O2 alkylation is substrate-dependent, so each case is confirmed by NMR or LC-MS; the N3-benzoyl can also be partially lost on long thermal steps.

Palladium-catalysed allylic substitution. With allylic esters and carbonates it serves as the nucleobase in carbocyclic uracil nucleoside assembly through a π-allyl Pd intermediate; double inversion gives net retention at the allylic carbon, opposite to Mitsunobu.

N1-alkylation with benzyl and primary alkyl halides (not secondary or tertiary).

Debenzoylation. Aqueous or methanolic ammonia cleaves the benzamide by addition–elimination, N3 departing as an amide anion stabilised by the flanking C2 and C4 carbonyls.

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Safety Information

Hazard Class None — not subject to transport regulations
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)

Documentation

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