Name: HATU
CAS#: 148893-10-1
Chemical Formula: C10H15F6N6OP
Exact Mass:
Molecular Weight: 380.24
Elemental Analysis: C, 31.59; H, 3.98; F, 29.98; N, 22.10; O, 4.21; P, 8.15
Synonym: 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, N-[(Dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide
IUPAC/Chemical Name: [dimethylamino(triazolo[4,5-b]pyridin-3-yloxy)methylidene]-dimethylazanium;hexafluorophosphate
SMILES Code: C/[N+](C)=C(N(C)C)\ON1N=NC2=CC=CN=C21.F[P-](F)(F)(F)(F)F
Description: HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid. HATU is used along with Hünig's base (N,N-diisopropylethylamine, DIPEA) to form amide bonds. Generally DMF is used as solvent, although other polar organic solvents can also be used. (Source: https://en.wikipedia.org/wiki/HATU).
1: Aaronson JG, Klein LJ, Momose AA, O'Brien AM, Shaw AW, Tucker TJ, Yuan Y, Tellers DM. Rapid HATU-mediated solution phase siRNA conjugation. Bioconjug Chem. 2011 Aug 17;22(8):1723-8. doi: 10.1021/bc2001227. Epub 2011 Jul 11. PubMed PMID: 21744777.
2: Hołyńska M, Kubiak M. Supramolecular motifs in the first structures of organic carboxylate salts of 1-(diaminomethylene)thiourea (HATU). Acta Crystallogr C. 2009 Aug;65(Pt 8):o410-3. doi: 10.1107/S0108270109026390. Epub 2009 Jul 15. PubMed PMID: 19652326.
3: Xiao Z, Yang MG, Li P, Carter PH. Synthesis of 3-substituted-4(3H)-quinazolinones via HATU-mediated coupling of 4-hydroxyquinazolines with amines. Org Lett. 2009 Mar 19;11(6):1421-4. doi: 10.1021/ol802946p. PubMed PMID: 19243133.
4: Yung A, Papworth-Smith J, Wilkinson SM. Occupational contact urticaria from the solid-phase peptide synthesis coupling agents HATU and HBTU. Contact Dermatitis. 2003 Aug;49(2):108-9. PubMed PMID: 14641366.
