Dibenzocyclooctyne-aMine for Copper-free Click CheMistry

Base Information

• Chemical Name: Dibenzocyclooctyne-aMine for Copper-free Click CheMistry
• CAS No.: 1255942-06-3
• Molecular Formula: C16H13N
• Molecular Weight: 276.338
• Hs Code.: 29339900
• Mol file: 1255942-06-3.mol

Synonyms:Dibenzocyclooctyne-aMine for Copper-free Click CheMistry;ADIBO-CH2CH2NH2·TFA;Azadibenzocyclooctyne-(CH2)2-amine TFA;DBCO-amine;DBCO-NH2;Dibenzocyclooctyne-amine

Chemical Property of Dibenzocyclooctyne-aMine for Copper-free Click CheMistry

Chemical Property:

• Melting Point: 86-96°C
• Boiling Point: 549.9±50.0 °C(Predicted)
• PKA: 8.81±0.10(Predicted)
• PSA: 46.33000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 3.04710
• Storage Temp.: ?20°C

Purity/Quality:

99%, ^*data from raw suppliers

DBCO-Amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: DBCO-amine is a simple building block containing a DBCO moiety and will add minimal spacer to the modified molecules. In the presence of activators such as EDC or HATU, this reagent can be used to derivatize carboxyl groups or activated esters (e.g. The NHS ester) through a stable amide bond. DBCO is commonly used for copper-free Click Chemistry reactions.
• Uses: Azadibenzocyclooctyne amine is a carbonyl reactive reagent used to incorporate ADIBO into organic compounds, surfaces or particlesAzadibenzocyclooctyne amine is widely useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. It reacts with azide functionalized compounds or bimolecules to give stable triazole linkage without a need for a Cu(I) catalyst. DBCO-Amine was useful for the study of labelled T-cells, which were used to predict the therapeutic efficacy of adoptive T-cell therapy.

Technology Process of Dibenzocyclooctyne-aMine for Copper-free Click CheMistry

There total 9 articles about Dibenzocyclooctyne-aMine for Copper-free Click CheMistry 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:

N-(3-trifluoroacetamidopropanoyl)-5,6-Dihydro-11,12-Didehydrodibenzo[b,f]azocine (1337920-23-6) → N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine (1255942-06-3)

Guidance literature:

With potassium carbonate; In methanol; water; at 20 ℃;

DOI:10.1021/bc100306u

Reference yield:

C20H17F3N2O2 → N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine (1255942-06-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium perbromide hydrobromide / dichloromethane / 20 °C

2: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C

3: potassium carbonate / methanol; water / 20 °C

With pyridinium perbromide hydrobromide; potassium tert-butylate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/bc100306u

Reference yield:

C20H17Br2F3N2O2 → N-(3-aminopropionyl)-5,6-dihydro-11,12-didehydrodibenzo[b,f]azocine (1255942-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C

2: potassium carbonate / methanol; water / 20 °C

With potassium tert-butylate; potassium carbonate; In tetrahydrofuran; methanol; water;

DOI:10.1021/bc100306u

upstream raw materials:

N-(3-trifluoroacetamidopropanoyl)-5,6-Dihydro-11,12-Didehydrodibenzo[b,f]azocine

dibenzo[b,f]azocin-6(5H)-one

(Z)-5,6-dihydrodibenzo[b,f]azocine

N-[tricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine

Downstream raw materials:

DBCO-PEG₄-amine

N-boc protected ADIBO-PEG₄-amine

DBCO-4PEG-biotin