2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

Base Information

• Chemical Name: 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
• CAS No.: 1296869-58-3
• Molecular Formula: C₂₁H₁₉BF₂N₂
• Molecular Weight: 348.203

Synonyms:2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

Chemical Property of 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

Chemical Property:

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Technology Process of 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine

There total 6 articles about 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine 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: 84.0%

C24H27BF2N2Si (1296869-57-2) → 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine (1296869-58-3)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol; for 0.25h;

DOI:10.1021/jo200491m

Reference yield: 30.0%

2-iodo-1,3,5,7-tetramethyl-8-phenyl-4,4-difluoro-4-bora-3a-azonia-4a-aza-s-indacence (1296869-56-1) + trimethylsilylacetylene (1066-54-2) → 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine (1296869-58-3)

Guidance literature:

2-iodo-1,3,5,7-tetramethyl-8-phenyl-4,4-difluoro-4-bora-3a-azonia-4a-aza-s-indacence; trimethylsilylacetylene; With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; In tetrahydrofuran; at 60 ℃; for 6h; Inert atmosphere;

With sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1039/c3dt51927a

Reference yield:

phenyl BODIPY → 2-ethynyl-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine (1296869-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1: calcium carbonate; benzyl triethylammonium dichloroiodate / methanol; dichloromethane / 1 h / 20 °C

2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 50 °C / Inert atmosphere

3: potassium carbonate / tetrahydrofuran; methanol / 0.25 h

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; triethylamine; calcium carbonate; benzyl triethylammonium dichloroiodate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo200491m

upstream raw materials:

2-iodo-1,3,5,7-tetramethyl-8-phenyl-4,4-difluoro-4-bora-3a-azonia-4a-aza-s-indacence

C₂₄H₂₇BF₂N₂Si

2,4-dimethyl-1H-pyrrole

benzoyl chloride

Downstream raw materials:

tetra-A-TAEB

para-BAEB

pyrazine TAEB

C₄₀H₃₆B₂F₄N₄

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