• Chemical structure of N3-Benzoylthymine, CAS 4330-20-5, ≥98% — N3-benzoyl-protected thymine nucleobase, a base-labile building block for nucleoside, oligonucleotide, and phosphoramidite synthesis. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
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NorrChemica™

N3-Benzoylthymine

CAS 4330-20-5 ≥98%

N3-Benzoylthymine | CAS 4330-20-5 | ≥98%

Pack sizes & prices

Pack size Excl. VAT
5.0 g−46% €87,05€47,17€9,43/g€59,20 incl. VAT
10 g−54% €170,32€78,25€7,83/g€98,20 incl. VAT
25 g−50% €317,93€157,93€6,32/g€198,20 incl. VAT
100 g−62% €1.055,98€396,97€3,97/g€498,20 incl. VAT

Prices are shown without VAT. The price in the box includes VAT at 25.5% for Finland. Shipping calculated at checkout.Free shipping on orders above €250 incl. VAT. For businesses in other EU countries that give a VAT number, the limit is €250 excl. VAT.

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Technical Specifications

CAS Number 4330-20-5
MDL Number MFCD12546342
SMILES CC1=CNC(=O)N(C1=O)C(=O)C2=CC=CC=C2
InChI InChI=1S/C12H10N2O3/c1-8-7-13-12(17)14(10(8)15)11(16)9-5-3-2-4-6-9/h2-7H,1H3,(H,13,17)
InChIKey FCQCLMZIGUFTQR-UHFFFAOYSA-N
PubChem CID 10933275
Molecular Formula C₁₂H₁₀N₂O₃
Molecular Weight 230.22 g/mol
Melting Point ~100 °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
Country of Origin Finland
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

3-Benzoylthymine is one of the main substrates for the synthesis of modified thymine derivatives. The electron-withdrawing benzoyl group renders the thymine ring more electron-poor and, by protecting the N3 imide, allows regioselective functionalisation at N1. The protecting group is readily removed with aqueous ammonia.

Mitsunobu coupling. As a pronucleophile it couples with non-sugar alcohols to build carbocyclic and homologated thymine nucleosides; this route has delivered targets as demanding as the conformationally locked bicyclo[3.1.0]hexene stavudine analogue N-MCD4T, active against both HIV-1 and HIV-2.

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

Palladium-catalysed allylic substitution. With allylic esters and carbonates it serves as the nucleobase in the assembly of further carbocyclic pyrimidine nucleosides; coupling proceeds with retention of configuration.

Oligonucleotide synthesis. Benzoylation of the thymine imide protects it against the irreversible side reactions that synthesis reagents would otherwise cause during chain assembly. The N3-benzoyl is cleaved under milder basic conditions than the N-acyl groups used on the purine bases, because the pyrimidine imide anion is stabilised by the flanking C2 and C4 carbonyls.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • Worldwide: 7–14 business days, selected locations.

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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