8.51006

HBTU

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

• Synonym(s): HBTU, 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H317
• Precautionary Statements: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1A
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable