Date published: 2025-10-3

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HATU (CAS 148893-10-1)

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Alternate Names:
2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; N,N,N′N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uroniumhexafluorophosphate
Application:
HATU is a peptide coupling reagent
CAS Number:
148893-10-1
Purity:
≥99%
Molecular Weight:
380.23
Molecular Formula:
C10H15N6O•PF6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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HATU is useful as a peptide coupling agent and a catalyst for selective acylation. It is also a reagent for reactions involving amide bond formations. HATU, a highly efficient coupling reagent, finds extensive use in solid and solution-phase peptide synthesis. In a comparative study, HATU demonstrated superior coupling yields and generated smaller enantiomers when compared to HBTU and TBTU. Although DMF is the typical solvent, other non-polar compounds are also employed. When in the presence of HOAt, HATU forms HOAt, leading to the creation of activated esters that display high sensitivity to amino acids. While a side reaction may produce guanidine by-products, the addition of HOBt helps mitigate this. Interestingly, although initially considered an urea-based salt, x-ray analysis revealed HATU′s structure to be that of a guanidinium oxide.


HATU (CAS 148893-10-1) References

  1. First total synthesis of N-4909 and its diastereomer; a stimulant of apolipoprotein E secretion in human hepatoma Hep G2 cells.  |  Yanai, M. and Hiramoto, S. 1999. J Antibiot (Tokyo). 52: 150-9. PMID: 10344569
  2. Synthesis of macrocyclic, potential protease inhibitors using a generic scaffold.  |  Dumez, E., et al. 2002. J Org Chem. 67: 4882-92. PMID: 12098301
  3. N-triazinylammonium tetrafluoroborates. A new generation of efficient coupling reagents useful for peptide synthesis.  |  Kamiński, ZJ., et al. 2005. J Am Chem Soc. 127: 16912-20. PMID: 16316237
  4. Total synthesis of (-)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation.  |  Pattenden, G., et al. 2008. Org Biomol Chem. 6: 1478-97. PMID: 18385855
  5. Novel polyoxazole-based cyclopeptides from Streptomyces sp. Total synthesis of the cyclopeptide YM-216391 and synthetic studies towards telomestatin.  |  Deeley, J., et al. 2008. Org Biomol Chem. 6: 1994-2010. PMID: 18480915
  6. Supramolecular motifs in the first structures of organic carboxylate salts of 1-(diaminomethylene)thiourea (HATU).  |  Hołyńska, M. and Kubiak, M. 2009. Acta Crystallogr C. 65: o410-3. PMID: 19652326
  7. Peptide bond-forming reagents HOAt and HATU are not mutagenic in the bacterial reverse mutation test.  |  Nicolette, J., et al. 2016. Environ Mol Mutagen. 57: 236-40. PMID: 26840011
  8. Evaluation of combined use of Oxyma and HATU in aggregating peptide sequences.  |  Caporale, A., et al. 2017. J Pept Sci. 23: 272-281. PMID: 28139012
  9. Formation of 2-Imino Benzo[e]-1,3-oxazin-4-ones from Reactions of Salicylic Acids and Anilines with HATU: Mechanistic and Synthetic Studies.  |  Leas, DA., et al. 2018. ACS Omega. 3: 781-787. PMID: 29399653
  10. Identification of unexpected unlabeled N,N-dimethylamide formation in the synthesis of deuterated fragment of ribociclib by a HATU-mediated coupling reaction.  |  Gai, K., et al. 2019. J Labelled Comp Radiopharm. 62: 62-66. PMID: 30375008
  11. Anaphylaxis Induced by Peptide Coupling Agents: Lessons Learned from Repeated Exposure to HATU, HBTU, and HCTU.  |  McKnelly, KJ., et al. 2020. J Org Chem. 85: 1764-1768. PMID: 31849224
  12. Novel Harmicines with Improved Potency against Plasmodium.  |  Marinović, M., et al. 2020. Molecules. 25: PMID: 32977642
  13. Engineering of 177Lu-labeled gold encapsulated into dendrimeric nanomaterials for the treatment of lung cancer.  |  Wang, Z., et al. 2022. J Biomater Sci Polym Ed. 33: 197-211. PMID: 34686102
  14. Hands-on synthesis of furanamides and evaluation of their antimicrobial activity.  |  Mercogliano, M., et al. 2022. Nat Prod Res. 1-8. PMID: 35700078

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

HATU, 5 g

sc-211580
5 g
$52.00

HATU, 25 g

sc-211580A
25 g
$190.00