• Chemical structure of Ethyl (thymin-1-yl)acetate, CAS 55036-34-5, ≥98% — N1-alkylated thymine derivative used as a nucleobase building block in oligonucleotide and PNA synthesis, and as a versatile intermediate for site-selective functionalization of the thymine scaffold. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.​​​​​​​​​​​​​​​​
  • ¹H NMR spectrum of Ethyl (thymin-1-yl)acetate (CAS 55036-34-5) in DMSO-d₆ at 300.0 K, Bruker Avance 599.69 MHz, 20 s relaxation delay, 8 scans. Thymine N–H at ~11.3 ppm (0.98); C6–H (H1) at ~7.5 ppm (1.00); N1-CH₂ (H2) at ~4.4 ppm (1.99); ester O-CH₂ at ~4.1 ppm (2.00); thymine 5-CH₃ at ~1.7 ppm (2.99); ester CH₃ at ~1.2 ppm (3.00). Confirms structure and ≥98% purity. Batch NOR55036345-25-1, analysed 17 March 2025, NorrChemica.
  • ¹³C NMR spectrum of Ethyl (thymin-1-yl)acetate (CAS 55036-34-5) in DMSO-d₆ at 298.1 K, Bruker Avance 150.79 MHz, 2 s relaxation delay, 1024 scans. Carbonyls C=O at 168.3, 164.3 and 151.0 ppm (ester + thymine C2/C4); thymine C6 (C–H) at 141.6 ppm; quaternary CH₃–C (C5) at 108.6 ppm; ester O–CH₂ at 61.1 ppm; N1–CH₂ at 48.4 ppm; thymine 5-CH₃ and ester CH₃ at 14.0 and 11.9 ppm. Confirms structure and ≥98% purity. Batch NOR55036345-25-1, NorrChemica.
  • gHSQC 2D NMR spectrum of Ethyl (thymin-1-yl)acetate (CAS 55036-34-5) in DMSO-d₆, Bruker Avance, correlating ¹H (F2, ~0–11 ppm) with ¹³C (F1, ~0–150 ppm) one-bond couplings. Cross-peaks confirm thymine C6–H at ~7.5/141 ppm; N1–CH₂ at ~4.4/48 ppm; ester O–CH₂ at ~4.1/61 ppm; thymine 5-CH₃ at ~1.7/12 ppm; ester CH₃ at ~1.2/14 ppm. Confirms structure of N1-alkylated thymine ester. NorrChemica.
  • gHMBC 2D NMR spectrum of Ethyl (thymin-1-yl)acetate (CAS 55036-34-5) in DMSO-d₆, Bruker Avance, correlating ¹H (F2, ~0.5–11.5 ppm) with ¹³C (F1, ~0–170 ppm) through long-range (²J, ³J) couplings. Cross-peaks from N1–CH₂ (~4.4 ppm) to thymine C2/C4 carbonyls (~150–168 ppm) and C6 (~141 ppm) confirm N1 attachment of the acetate arm; correlations from ester O–CH₂ (~4.1 ppm) and CH₃ (~1.2 ppm) to the ester C=O (~168 ppm) confirm the ethyl ester. NorrChemica.
  • gCOSY 2D NMR spectrum of Ethyl (thymin-1-yl)acetate (CAS 55036-34-5) in DMSO-d₆, Bruker Avance, showing homonuclear ¹H–¹H scalar (²J, ³J) correlations across both F1 and F2 (~1–11.5 ppm). Diagonal peaks reproduce the 1D ¹H spectrum; off-diagonal cross-peaks confirm coupling between the ester O–CH₂ (~4.1 ppm) and ester CH₃ (~1.2 ppm), and a weak ⁴J allylic coupling between thymine C6–H (~7.5 ppm) and 5-CH₃ (~1.7 ppm). N–H at ~11.3 ppm shows no scalar coupling cross-peak. NorrChemica.
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NorrChemica™

Ethyl (Thymin-1-yl)acetate

CAS 55036-34-5 ≥98%

Ethyl (Thymin-1-yl)acetate | CAS 55036-34-5 | ≥98%

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Technical Specifications

CAS Number 55036-34-5
MDL Number MFCD07200411
SMILES CCOC(=O)CN1C=C(C(=O)NC1=O)C
InChI InChI=1S/C9H12N2O4/c1-3-15-7(12)5-11-4-6(2)8(13)10-9(11)14/h4H,3,5H2,1-2H3,(H,10,13,14)
InChIKey PZOFYXHUJOBREJ-UHFFFAOYSA-N
PubChem CID 565853
Molecular Formula C₉H₁₂N₂O₄
Molecular Weight 212.2 g/mol
Melting Point 173-174 °C
Solubility Soluble in ethanol, DMF, DMSO, and ethyl acetate; sparingly soluble 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

Ethyl (thymin-1-yl)acetate is an N1-alkylated thymine bearing an acetic-acid ethyl-ester tether — the canonical entry point to the thymine nucleobase acetic-acid building block. Alkaline hydrolysis (LiOH or NaOH in aqueous EtOH or THF) releases thymin-1-ylacetic acid, which couples through standard peptide chemistry (HBTU, HATU, EDC, DCC, or PyBOP with a non-nucleophilic base) to amine partners.

PNA monomer synthesis (the principal use). The liberated acid couples to orthogonally protected N-(2-aminoethyl)glycine (AEG) — Boc-AEG-OEt/OBn for t-Boc/Cbz, Fmoc-AEG-OBn for Fmoc/Bhoc — to give the protected thymine PNA monomer. Thymine is the only canonical PNA nucleobase needing no exocyclic-amine protection, making this the shortest of the four monomer routes. The resulting oligomers hybridise sequence-specifically with DNA and RNA by Watson–Crick pairing; the uncharged polyamide backbone removes phosphate–phosphate repulsion and gives high nuclease/protease stability.

Adenine receptors. Coupled to amine-functionalised macrocyclic, peptidic, or polymeric scaffolds, the thymine units recognise adenine, adenosine, AMP, and ATP by Watson–Crick hydrogen bonding in organic or mixed aqueous media. Mono- and bis-thymine calix[4]arenes are a documented example.

Nucleobase-functionalised polymers. Grafted onto polymer backbones to install thymine hydrogen-bonding sites for non-covalent self-assembly. Thymine-terminated PEG undergoes heterocomplementary supramolecular polymerisation with diamino-triazine PEG; complementary pairing with adenine- or triazine-bearing partners creates reversible cross-links for template-directed polymerisation and adenine-responsive materials.

Pseudopeptide backbones. Coupled to natural and non-natural amino acids, reduced-peptide-bond pseudodipeptides, and chiral amino-alcohol scaffolds to deliver conformationally constrained PNA-style monomers and thymine–peptide hybrids.

C5-methyl functionalisation. Radical bromination (NBS/AIBN) gives bromomethyl intermediates for displacement by O-, N-, S-, or C-nucleophiles, installing fluorescent, affinity-tag, or other substituents en route to 5-substituted PNA monomers; the ester protects the carboxylate, then hydrolyses.

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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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