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
• Uses: HBTU is a coupling reagent used in peptide synthesis. HBTU has been shown to effectively suppress racemization. peptide coupling reagent that reduces racemization

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-methylbenzenesulfonamide

2-amino-5-[(2’R,4’S,5’R)-4’-hydroxy-5’-(hydroxymethyl)tetrahydrofuran-2’-yl]pyrimidin-4(3H)-one

3-nitro-N-(1H-benzoimidazol-2-yl)-benzamide

Refernces

• 1、 -. "Method of forming N-protected amino acid thiohydantoins". . . Retrieved 2008/06/13.
• 2、 Dourtoglou,Gross. "O-benzotriazolyl-N,N,N',N'-tetramethyluronium hexafluorophosphate as coupling reagent for the synthesis of peptides of biological interest". . p. 572 - 574. Retrieved 2007/10/02.