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HBTU information


HBTU
HBTU Structural Formula
Names
IUPAC name
[benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium;hexafluorophosphate[1]
Other names
  • HBTU

  • 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

  • 3-[Bis(dimethylamino)methyliumyl]-3H-benzotriazol-1-oxide hexafluorophosphate
Identifiers
CAS Number
  • 94790-37-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 2014894 checkY
ECHA InfoCard 100.133.815 Edit this at Wikidata
EC Number
  • 619-076-7
PubChem CID
  • 2733084
UNII
  • X5I03TZQ8D checkY
CompTox Dashboard (EPA)
  • DTXSID00915302 Edit this at Wikidata
InChI
  • InChI=1S/C11H16N5O.F6P/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;1-7(2,3,4,5)6/h5-8H,1-4H3;/q+1;-1
    Key: UQYZFNUUOSSNKT-UHFFFAOYSA-N
SMILES
  • CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
Properties
Chemical formula
C11H16F6N5OP
Molar mass 379.247 g·mol−1
Appearance White crystals
Melting point 200 °C (392 °F; 473 K)
Hazards[2]
Occupational safety and health (OHS/OSH):
Main hazards
Irritant
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P210, P240, P241, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

HBTU (Hexafluorophosphate Benzotriazole Tetramethyl Uronium) is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization.[3][4] It is used because of its mild activating properties.[5]

The product obtained by reaction of HOBt with tetramethyl chloro uronium salt (TMUCl) was assigned to a uronium type structure, presumably by analogy with the corresponding phosphonium salts, which bear a positive carbon atom instead of the phosphonium residue. Later, it was shown by X-ray analysis that salts crystallize as aminium rather than the corresponding uronium salts.[6][7]

  1. ^ CID 2733084 from PubChem
  2. ^ "2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate". pubchem.ncbi.nlm.nih.gov.
  3. ^ Dourtoglou, Vassilis. (April 1978). "L'hexafluorophosphate de O-benzotriazolyl-N,N-tetramethyluronium: Un reactif de couplage peptidique nouveau et efficace". Tetrahedron Letters. 19 (15): 1269–1272. doi:10.1016/0040-4039(78)80103-8.
  4. ^ Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. (1989). "New coupling reagents in peptide chemistry". Tetrahedron Letters. 30 (15): 1927–1930. doi:10.1016/S0040-4039(00)99616-3.
  5. ^ Solange, A. (1992). "HBTU: a mild activating agent of muramic acid". Bioorganic & Medicinal Chemistry Letters. 2 (6): 571–574. doi:10.1016/S0960-894X(01)81199-9.
  6. ^ Carpino, L.; Imazumi, H.; El-Faham, A.; Ferrer, F.; Zhang, C.; Lee, Y.; Foxman, B.; Henklein, P.; Hanay, C.; Mügge, C.; Wenschuh, H.; Klose, J.; Beyermann, M.; Bienert, M. (2002). "The uronium/guanidinium peptide coupling reagents: Finally the true uronium salts". Angewandte Chemie International Edition. 41 (3): 441–445. doi:10.1002/1521-3773(20020201)41:3<441::AID-ANIE441>3.0.CO;2-N. PMID 12491372.
  7. ^ Abdelmoty, I.; Albericio, F.; Carpino, L.; Foxman, B.; Kates, S. (1994). "Structural studies of reagents for peptide bond formation: Crystal and molecular structures of HBTU and HATU". Letters in Peptide Science. 1 (2): 57–67. doi:10.1007/BF00126274. S2CID 38746650.

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