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445460

Sigma-Aldrich

HATU

97%, for peptide synthesis

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H15F6N6OP
CAS Number:
148893-10-1
Molecular Weight:
380.23
MDL number:
MFCD27957364
UNSPSC Code:
12352302
PubChem Substance ID:
24868183
NACRES:
NA.22

product name

HATU, 97%

Quality Level

200

Assay

97%

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

183-185 °C (lit.)

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

SMILES string

F[P-](F)(F)(F)(F)F.CN(C)[C+](N(C)C)n1n[n+]([O-])c2ncccc12

InChI

1S/C10H15N6O.F6P/c1-13(2)10(14(3)4)15-8-6-5-7-11-9(8)16(17)12-15;1-7(2,3,4,5)6/h5-7H,1-4H3;/q+1;-1

InChI key

FKBFHOSFPRWJNV-UHFFFAOYSA-N

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Application

Reagent for:
Synthesis of Aurora A kinase inhibitors
HPLC assay to determine D- and L- acid enantiomers in human plasma
Amide bond formation reactions

Catalyst for:
Selective acylation
Selecocyclization-oxidation deselenation sequence
Peptide coupling reagent.
Preparation of N-arylsulfonamide-linked peptides by solid-phase synthesis.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1A

Supplementary Hazards

EUH044

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK8563
STBK7852
STBK4805
WXBD6237V
STBK3650

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Pept., Proceedings of the European Peptide Symposium., ed. U. Ragnarrson, 27, 272-273 (2002)
Yi He et al.
Organic letters, 8(12), 2483-2485 (2006-06-02)
N-Acylsulfonamide safety-catch linkers are versatile tools in solid-phase organic synthesis because of their stability. This stability necessitates linker activation prior to compound cleavage. Here, we demonstrate that the N-acylsulfonamide group can react with a pi-allyl palladium complex and that these
J. Prakt. Chem./Chem.-Ztg., 340, 581-583 (1998)
Lett. Pept. Sci., 9, 119-123 (2003)
Mazen Jamous et al.
Nuclear medicine and biology, 41(6), 464-470 (2014-05-02)
The gastrin-releasing peptide receptor (GRPR) was shown to be expressed with high density on several types of cancers. Radiolabeled peptides for imaging and targeted radionuclide therapy have been developed. In this study, we evaluated the potential of statine-based bombesin antagonists
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COMU-Safer and More Efficient Peptide Coupling Reagent

COMU is a non-explosive coupling agent suitable for solution phase & solid phase peptide synthesis. Its activity meets or exceeds that of HATU and its water-soluble by-product are easily removed.

Greener Chemistry: Methods and Products for Amide Bond Formation

Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.

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