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Merck

8.51006

HBTU

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C11H16F6N5OP
Número CAS:
94790-37-1
Peso molecular:
379.24
UNSPSC Code:
12352107
EC Index Number:
423-020-5
NACRES:
NA.22
MDL number:
MFCD00075445

Nombre del producto

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

SMILES string

[N+](=C(N(C)C)O[n]1nnc2c1cccc2)(C)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

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

Quality Level

300

Categorías relacionadas

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

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).

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.

Other Notes

Replaces: 01-62-0010

Legal Information

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1A

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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