8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

Base Information

• Chemical Name: 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene
• CAS No.: 1380170-45-5
• Molecular Formula: C₃₅H₃₈BN₂P
• Molecular Weight: 528.485
• Mol file: 1380170-45-5.mol

Synonyms:8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

Chemical Property of 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

There total 6 articles about 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene 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: 92.0%

8-[(4-diethylphosphonato)phenyl]-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1380170-44-4) → 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1380170-45-5)

Guidance literature:

With lithium aluminium tetrahydride; chloro-trimethyl-silane; In tetrahydrofuran; at -40 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201108416

Reference yield:

8-(4-bromophenyl)-4,4-difluoro-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1159853-70-9) → 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1380170-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 20 °C

2: palladium diacetate; N-ethyl-N,N-diisopropylamine; 1,4-di(diphenylphosphino)-butane / dimethyl sulfoxide / 72 h / 90 °C / Inert atmosphere

3: lithium aluminium tetrahydride; chloro-trimethyl-silane / tetrahydrofuran / -40 - 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; chloro-trimethyl-silane; palladium diacetate; N-ethyl-N,N-diisopropylamine; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; diethyl ether; dimethyl sulfoxide;

DOI:10.1002/anie.201108416

Reference yield:

2,4-dimethyl-3-ethyl-pyrrole (517-22-6) → 8-((4-phosphino)phenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene (1380170-45-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere; Darkness; Schlenk technique

1.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique; Darkness

1.3: 20 °C

2.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dimethyl sulfoxide / 42 h / 90 °C / Inert atmosphere; Schlenk technique

3.1: tetrahydrofuran; diethyl ether / 3 h / 20 °C / Inert atmosphere; Schlenk technique

4.1: lithium aluminium tetrahydride; chloro-trimethyl-silane / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

With lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1055/s-0034-1378336

upstream raw materials:

8-(4-bromophenyl)-4,4-difluoro-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

8-(4-bromophenyl)-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

8-[(4-diethylphosphonato)phenyl]-4,4-diphenyl-1,3,5,7-tetramethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene

phenyllithium