1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-

Base Information

• Chemical Name: 1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-
• CAS No.: 1334179-85-9
• Molecular Formula: C₁₉H₃₀N₁₀O₂
• Molecular Weight: 430.513
• Mol file: 1334179-85-9.mol

Synonyms:1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-;(4-{[Bis-(1-tert-butyl-1H-[1,2,3]triazol-4-ylmethyl)-amino]-methyl}-[1,2,3]triazol-1-yl)-acetic acid;BTTAA;(4-{[Bis-(1-tert-butyl-1H-[1,2,3]triazol-4-ylmethyl)-amino]-methyl}-[1,2,3]triazol-1-yl)-acetic acid (other name: BTTAA)

Chemical Property of 1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 115.5 - 116.5 °C
• Boiling Point: 620.7±65.0 °C(Predicted)
• PKA: 3.33±0.10(Predicted)
• PSA: 132.67000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 1.25810
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO, DMF, MeOH

Purity/Quality:

98%,99%, ^*data from raw suppliers

BTTAA ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: BTTP is a newest generation, accelerating ligand for CuAAC that provides much greater rate enhancement compared to previous generation ligands (e.g. THPTA or TBTA). More importantly, it minimizes perturbations to the physiological state of the cells or organisms probed and allows for effective bioconjugation with suppressed cell cytotoxicity by further lowering copper loading in the catalyst formulation. Nature Communications. 5: 4981(2014) Chem Asian J., 6(10), 2796-802(2011)
• Uses: BTTAA is a next-generation, water-soluble ligand for the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) that dramatically accelerates reaction rates and suppresses cell cytotoxicity. The biocompatibility and fast kinetics of BTTAA are advancements from water-insoluble TBTA and are desirable for bio conjugation in diverse chemical biology experiments.

Technology Process of 1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]-

There total 3 articles about 1H-1,2,3-Triazole-1-acetic acid, 4-[[bis[[1-(1,1-diMethylethyl)-1H-1,2,3-triazol-4-yl]Methyl]aMino]Methyl]- 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: 76.0%

2-azidoacetic acid (18523-48-3) + N,N-bis((1-(tert-butyl)-1H-1,2,3-triazol-4-yl)methyl)prop-2-yn-1-amine (1257633-68-3) → BTTAA (1334179-85-9)

Guidance literature:

With tris(triphenylphosphine) copper(I) bromide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 60 ℃;

Reference yield:

1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1257633-67-2) → BTTAA (1334179-85-9)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / water; dichloromethane; ethyl acetate / 3 h / Inert atmosphere

2: sodium tris(acetoxy)borohydride / water; 1,2-dichloro-ethane / 40 h / 20 °C

3: N-ethyl-N,N-diisopropylamine; tris(triphenylphosphine) copper(I) bromide / tetrahydrofuran / 60 °C

With tris(triphenylphosphine) copper(I) bromide; sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane;

Reference yield:

1-(tert-butyl)-1H-1,2,3-triazole-4-carbaldehyde (129027-65-2) → BTTAA (1334179-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tris(acetoxy)borohydride / water; 1,2-dichloro-ethane / 40 h / 20 °C

2: N-ethyl-N,N-diisopropylamine; tris(triphenylphosphine) copper(I) bromide / tetrahydrofuran / 60 °C

With tris(triphenylphosphine) copper(I) bromide; sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; 1,2-dichloro-ethane;

upstream raw materials:

2-azidoacetic acid

N,N-bis((1-(tert-butyl)-1H-1,2,3-triazol-4-yl)methyl)prop-2-yn-1-amine

1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole

1-(tert-butyl)-1H-1,2,3-triazole-4-carbaldehyde

Refernces

• 1、 -. "LIGANDS AND METHODS FOR LABELING BIOMOLECULES IN VIVO". Paragraph 0073; 0074. . Retrieved 2013/11/19.