• Chemical structure of N1-Acetylthymine, CAS 13251-16-6, ≥99% — N1-acylated thymine derivative used as a protected nucleobase building block in oligonucleotide synthesis, regioselective N1 vs N3 functionalization studies, and as a synthetic intermediate in nucleoside chemistry. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.
  • ¹H NMR spectrum of N1-Acetylthymine (CAS 13251-16-6) in DMSO-d₆ at 298.1 K, Bruker Avance 400.15 MHz, 10 s relaxation delay, 8 scans. Thymine N–H at ~11.5 ppm (1.02); C6–H at ~8.0 ppm (1.03); acetyl CO–CH₃ at ~2.5 ppm (2.99); thymine 5-CH₃ at ~1.9 ppm (3.00). Confirms structure and ≥99% purity. Batch NOR13251166-25-2, analysed 15 June 2025, NorrChemica.
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NorrChemica™

N1-Acetylthymine

CAS 13251-16-6 ≥99%

N1-Acetylthymine | CAS 13251-16-6 | ≥99%

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Technical Specifications

CAS Number 13251-16-6
MDL Number MFCD00887709
SMILES CC1=CN(C(=O)NC1=O)C(=O)C
InChI InChI=1S/C7H8N2O3/c1-4-3-9(5(2)10)7(12)8-6(4)11/h3H,1-2H3,(H,8,11,12)
InChIKey YBXJEAPQVULNKE-UHFFFAOYSA-N
PubChem CID 667607
Molecular Formula C₇H₈N₂O₃
Molecular Weight 168.15 g/mol
Solubility Soluble in DMF, DMSO, and ethanol; sparingly soluble in water
Purity ≥99%
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

N1-Acetylthymine blocks N1 tautomerism, inverts the usual thymine preferential reactivity at N1 and leaves the N3 imide as the only N-H site amenable for deprotonation under basic conditions and trapping with alkylating, acylating, or linker reagents. The acetyl is labile enough that careful control of the reaction conditions allows either the direct obtention of N1-acetyl-N3-substituted thymine derivatives or the acetyl acting as a transient protecting group that is concomitantly removed yielding the N3-substituted derivatives.

Mild acetyl-transfer reagent. The N1-acetyl sits in an N-acyl pyrimidinone/acyl-imide environment rather than an ordinary dialkylamide — an activated acyl donor transferring to nucleophiles under mild conditions, softer than acetic anhydride or acetyl chloride for sensitive substrates, and a model for the N-acyl pyrimidinone class. Transfer regenerates thymine and is followed by HPLC, LC-MS, or NMR.

Deacetylation methodology. The N1-acetyl is a model handle for screening N-acetyl cleavage rates and checking whether N3 substituents, C5 side chains, or other sensitive groups survive basic or nucleophilic work-up, and for tracking N-acyl migration and over-acylation.

C5-methyl chemistry. With N1 silent, the C5-methyl remains open to bromomethyl, hydroxymethyl, formyl, aminomethyl, thiomethyl, and related derivatives, each tested on the scaffold since N-acyl protection, acidity, and work-up can change the outcome.

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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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