2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

Base Information

• Chemical Name: 2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate
• CAS No.: 94790-37-1
• Molecular Formula: C11H16N5O^.PF6
• Molecular Weight: 379.245
• Hs Code.: HOSPHATE PRODUCT IDENTIFICATION
• European Community (EC) Number: 423-020-5,619-076-7
• DSSTox Substance ID: DTXSID101335774
• Wikipedia: HBTU
• Wikidata: Q19787025
• Mol file: 94790-37-1.mol

Synonyms:N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methylmethanaminium hexafluorophosphate;O-HBTU cpd

Chemical Property of 2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Melting Point: 200- 202 °C
• Flash Point: 200°C
• PSA: 59.78000
• LogP: 3.43200
• Storage Temp.: 2-8°C
• Solubility.: acetonitrile: 0.1 g/mL, clear
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 379.09966612
• Heavy Atom Count: 24
• Complexity: 350

Purity/Quality:

≥99% ^*data from raw suppliers

HBTU ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-42/43
• Safety Statements: 26-36/37/39-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Triazoles
• Canonical SMILES: CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1.F[P-](F)(F)(F)(F)F
• General Description: HBTU (o-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate) is a peptide coupling reagent commonly used in solid-phase synthesis to activate carboxylic acids for amide bond formation. It is particularly effective in oligonucleotide conjugate synthesis, where it facilitates the efficient coupling of functional groups like amino acids or cholesterol to oligonucleotides. HBTU, along with other activation reagents such as PyBOP and EDC, plays a key role in improving conjugation yields and reaction efficiency in solid-support modifications.

Technology Process of 2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

There total 4 articles about 2-(1h-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzotriazol-1-ol (2592-95-2) + N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate → O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (94790-37-1)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1055/s-1984-30895

Reference yield:

tetramethylurea (632-22-4) → O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (94790-37-1)

Guidance literature:

Multi-step reaction with 3 steps

1: phosgene / toluene / 0.25 h

2: aq. ammonium hexafluorophosphate / CH₂Cl₂

3: 100 percent / N(C₂H₅)3 / CH₂Cl₂

With phosgene; ammonium hexafluorophosphate; triethylamine; In dichloromethane; toluene;

DOI:10.1055/s-1984-30895

Reference yield:

N,N,N',N'-tetramethylchlorformamidinium chloride (56043-45-9,13829-06-6) + 1-Hydroxy-1,2,3-benzotriazole potassium salt (62244-77-3) → O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (94790-37-1)

Guidance literature:

With potassium hexafluorophosphate; potassium chloride;

DOI:10.1016/S0040-4039(00)99616-3

upstream raw materials:

N,N,N',N'-tetramethylchlorformamidinium chloride

1-Hydroxy-1,2,3-benzotriazole potassium salt

benzotriazol-1-ol

tetramethylurea

Downstream raw materials:

Z-Aib-OBt

N?[bis(dimethylamino)methylene]?4?chlorobenzenesulfonamide

Refernces

Total syntheses of bacillamide C and neobacillamide A; Revision of their absolute configurations

10.1016/j.tetasy.2013.11.001

The study focuses on the total syntheses of both enantiomers of bacillamide C and neobacillamide A, natural products with bioactivity, and their optical activities. The researchers aimed to resolve the confusion regarding the absolute configurations of these metabolites, which have been derived from microorganisms growing in marine and terrestrial environments. They synthesized the compounds using a stereospecific route from D-(-)-alanine and compared the specific rotation of the synthesized compounds to those reported in literature. The results indicated that the absolute configurations previously proposed for bacillamide C and neobacillamide A should be revised to (S). This finding is significant for genomic studies of their biosynthesis and for the use of bacillamide C as a building block in bioactive cyclic peptides.

Efficient synthesis of oligonucleotide conjugates on solid-support using an (aminoethoxycarbonyl)aminohexyl group for 5′-terminal modification

10.1016/j.bmcl.2009.02.121

The research discusses the development and application of a new amino-linker, (aminoethoxycarbonyl)aminohexyl group (ssH-linker), for the efficient synthesis of oligonucleotide conjugates on solid-support at the 5'-terminal primary amine. The purpose of this study was to improve the modification efficacy of oligonucleotides (ONTs) for gene detection or gene delivery by attaching functional groups like fluorophores, hydrophobic molecules, or peptides. The ssH-linker was found to be superior to the conventional 6-aminohexyl group (C6-linker) in terms of the rapid removal of amino-protecting groups and the efficient covalent connection with activated amino acids or cholesterol molecules. The study concluded that the ssH-linker is a useful terminal modification for solid-support conjugation of functional molecules, offering higher conjugation yields and faster deprotection compared to the C6-linker. Key chemicals used in the process included monomethoxytrityl (MMT) as a protecting group, N-protected phenylalanine (N-Fmoc-Phe) and its pentafluorophenyl ester (N-Fmoc-Phe-OPfp) for amino acid conjugation, and cholesteryl chloroformate for conjugation with cholesterol. Activation reagents such as (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) were also utilized in the coupling reactions.