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Sigma-Aldrich

HBTU

≥99.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

HBTU, 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C11H16F6N5OP
CAS Number:
94790-37-1
Molecular Weight:
379.24
MDL number:
MFCD00075445
UNSPSC Code:
12352107
EC Index Number:
423-020-5
NACRES:
NA.22

product name

HBTU, 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate Novabiochem®

Quality Level

300

product line

Novabiochem®

Assay

≥99.0% (HPLC)

form

powder

potency

>2000 mg/kg LD50, oral (Rat)

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

pH

4.1 (1.6 g/L in H2O)

mp

250 °C

solubility

1.6 g/L

application(s)

peptide synthesis

storage temp.

2-8°C

InChI

1S/C11H16N5O/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16/h5-8H,1-4H3/q+1

InChI key

CLZISMQKJZCZDN-UHFFFAOYSA-N

Related Categories

General description

TBTU and HBTU are two of the most popular in situ activation reagents used in solid phase and solution phase peptide synthesis [1,2,3,4,5,6,7,8,9]. These reagents offer reactivity similar to symmetrical anhydrides and BOP [1]. Couplings proceed smoothly and rates can even be enhanced by the addition of HOBt [2,4,5,6]. In addition to having high reactivity, TBTU and HBTU have also been shown to limit enantiomerization during fragment condensation and during DMAP catalyzed esterification of arginine derivatives [3]. Comparative experiments between HBTU and TBTU have shown that the counter ion has no influence on coupling rates or levels of enantiomerization [1].

Associated Protocols and Technical Articles
Guide to Selection of Coupling Reagents

Literature references

[1] R. Knorr, et al. (1989) Tetrahedron Lett., 30, 1927.
[2] M. S. Bernatowicz, et al. (1989) Tetrahedron Lett., 30, 4645.
[3] D. Ambrosius, et al. (1989) Biol. Chem. Hoppe-Seyler, 370, 217.
[4] C. G. Fields, et al. (1991) Pept. Res., 4, 95.
[5] A. G. Beck-Sickinger, et al. (1991) Pept. Res., 4, 88.
[6] G. E. Reid, et al. (1992) Anal. Biochem., 200, 301.
[7] G. B. Fields, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 1st International Symposium′, R. Epton (Eds), SPCC UK Ltd., Birmingham, 1990, pp. 241.
[8] P. A. Baybayan, et al. in ′Peptides, Chemistry & Biology, Proc. 12th American Peptide Symposium′, J. A. Smith & J. E. Rivier (Eds), ESCOM, Leiden, 1992, pp. 566.
[9] J. J. Dudash, et al. (1993) Synth. Commun., 23, 349.

Application

  • Synthesis of Quinoxaline Derivatives Using HBTU: A study highlighting the use of HBTU as a Lewis acid catalyst for synthesizing quinoxaline derivatives, presenting a mild and green protocol (Popatkar and Meshram, 2020).
  • Efficient Conversion of Carboxylic Acids into Benzimidazoles: Details an HBTU-promoted methodology for converting carboxylic acids into benzimidazoles in a one-pot strategy (Barasa and Yoganathan, 2018).
  • Synthesis of Malonyl-linked Glycoconjugates: Discusses the use of HBTU in the synthesis of glycoconjugates, comparing its efficiency with other reagents (Nörrlinger et al., 2016).

Linkage

Replaces: 01-62-0010

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1A

Storage Class Code

11 - Combustible Solids

WGK

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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