DBCO-C6-NHS ester

Base Information

• Chemical Name: DBCO-C6-NHS ester
• CAS No.: 1384870-47-6
• Molecular Formula: C₂₅H₂₂N₂O₅
• Molecular Weight: 430.46
• Hs Code.: 2942000090
• Mol file: 1384870-47-6.mol

Synonyms:1-{[6-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-6-oxohexanoyl]oxy}pyrrolidine-2,5-dione

Chemical Property of DBCO-C6-NHS ester

Chemical Property:

• Boiling Point: 685.5±65.0 °C(Predicted)
• PKA: -0.17±0.20(Predicted)
• Density: 1.37±0.1 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

DBCO-C6-NHSester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: DBCO-C6-NHS ester is an amine-reactive compound, which can be used to modify an amine-containing molecule in organic media. This reagent isn't soluble in aqueous media. The extended 6-carbon atom spacer arm improves solubility in commonly used organic solvents including dichloromethane, chloroform, THF, and ethyl acetate and it also improves derivatization efficiency and stability of conjugates. DBCO is commonly used for copper-free Click Chemistry reactions.

Technology Process of DBCO-C6-NHS ester

There total 7 articles about DBCO-C6-NHS ester 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:

dibenzosuberenon (2222-33-5) → 1-{[6-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-6-oxohexanoyl]oxy}pyrrolidine-2,5-dione (1384870-47-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: hydroxylamine hydrochloride; pyridine / ethanol / 12 h / Reflux

2.1: Eaton’s reagent / 0.5 h / 100 °C

3.1: lithium aluminium tetrahydride / diethyl ether / 15 h / Reflux

4.1: dichloromethane / 12 h / 20 °C

4.2: 12 h / 75 °C

5.1: bromine / dichloromethane / 8 h / 0 °C

6.1: potassium tert-butylate / tetrahydrofuran / 2 h / -40 °C

7.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide

With pyridine; lithium aluminium tetrahydride; Eaton’s reagent; hydroxylamine hydrochloride; potassium tert-butylate; bromine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.202009408

Reference yield:

N-[tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,9,12,14-heptaen-2-ylidene]hydroxylamine (1021-91-6) → 1-{[6-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-6-oxohexanoyl]oxy}pyrrolidine-2,5-dione (1384870-47-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Eaton’s reagent / 0.5 h / 100 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 15 h / Reflux

3.1: dichloromethane / 12 h / 20 °C

3.2: 12 h / 75 °C

4.1: bromine / dichloromethane / 8 h / 0 °C

5.1: potassium tert-butylate / tetrahydrofuran / 2 h / -40 °C

6.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide

With lithium aluminium tetrahydride; Eaton’s reagent; potassium tert-butylate; bromine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.202009408

Reference yield:

5,6,11,12-tetrahydrodibenz[b,f]azocin-6-one (6047-29-6) → 1-{[6-(11,12-didehydrodibenzo[b,f]azocin-5(6H)-yl)-6-oxohexanoyl]oxy}pyrrolidine-2,5-dione (1384870-47-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 15 h / Reflux

2.1: dichloromethane / 12 h / 20 °C

2.2: 12 h / 75 °C

3.1: bromine / dichloromethane / 8 h / 0 °C

4.1: potassium tert-butylate / tetrahydrofuran / 2 h / -40 °C

5.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide

With lithium aluminium tetrahydride; potassium tert-butylate; bromine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/anie.202009408

upstream raw materials:

dibenzosuberenon

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

5,6,11,12-tetrahydrodibenz[b,f]azocin-6-one

1-hydroxy-pyrrolidine-2,5-dione

Refernces