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8.51013

Sigma-Aldrich

HATU

for peptide synthesis, Novabiochem®

Synonym(s):

HATU, 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):
C10H15N6O · F6P
CAS Number:
148893-10-1
Molecular Weight:
380.23
MDL number:
MFCD27957364
UNSPSC Code:
12352107
NACRES:
NA.22

product name

HATU, Novabiochem®

Quality Level

300

product line

Novabiochem®

form

solid

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

mp

186 °C (decomposes)

application(s)

peptide synthesis

storage temp.

2-8°C

InChI

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

InChI key

WXIONIWNXBAHRU-UHFFFAOYSA-N

General description

A highly efficient coupling reagent for solid and solution phase peptide synthesis. In comparative studies HATU has been found to give better coupling yields with less enantiomerization that HBTU, TBTU or PyBOP®[1,2,3]. It is particularly effective at coupling to N-alkyl amines where other coupling reagents give poor yields and is the preferred reagent for loading resins bearing secondary amino groups.

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references

[1] L. A. Carpino (1993) J. Am. Chem. Soc., 115, 4397.
[2] F. Albericio, et al. (1998) J. Org. Chem., 63, 9678.
[3] J. A. Carpino, et al., in "Innovation & Perspectives in Solid Phase Synthesis, 3rd International Symposium", R. Epton (Ed.), Mayflower Worldwide Ltd., 1994, pp. 95.

Linkage

Replaces: 01-62-0041

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Identity (NMR, 1H): passes test
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

4.1A - Other explosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Articles

Peptide Coupling Reagents Guide

Novabiochem® coupling reagents for in situ activation are fast-reacting and compatible with various amino acids.

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