8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Base Information

• Chemical Name: 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• CAS No.: 1357004-01-3
• Molecular Formula: C₂₀H₁₈BF₅N₂
• Molecular Weight: 392.179

Synonyms:8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Chemical Property of 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

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Technology Process of 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

There total 4 articles about 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-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: 63.0%

boron trifluoride diethyl etherate (109-63-7) + C20H19F3N2 → 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1357004-01-3)

Guidance literature:

C₂₀H₁₉F₃N₂; With triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.8b00022

Reference yield: 60.0%

2,4-dimethyl-1H-pyrrole (625-82-1) + 4-Trifluoromethylbenzaldehyde (455-19-6) + boron trifluoride diethyl etherate (109-63-7) → 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1357004-01-3)

Guidance literature:

2,4-dimethyl-1H-pyrrole; 4-Trifluoromethylbenzaldehyde; With trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 4h; Cooling with ice;

boron trifluoride diethyl etherate; With triethylamine; In dichloromethane; at 20 ℃; for 2h; regioselective reaction;

DOI:10.1021/acs.orglett.6b00547

Reference yield:

4-trifluoromethyl-phenyl acetyl chloride (329-15-7) → 8-(4-trifluoromethylphenyl)-1,3,5,7-tetramethyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1357004-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 48 h / Reflux; Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With triethylamine; In dichloromethane;

DOI:10.1021/acsmedchemlett.8b00022

upstream raw materials:

2,4-dimethyl-1H-pyrrole

4-Trifluoromethylbenzaldehyde

boron trifluoride diethyl etherate

4-trifluoromethyl-phenyl acetyl chloride

Downstream raw materials:

2-bromo-4,4-difluoro-1,3,5,7-tetramethyl-8-[4-(trifluoromethyl)phenyl]-4-bora-3a,4a-diaza-s-indacene

2,8-dibromo-5,5-difluoro-1,3,7,9-tetramethyl-10-(4-(trifluoromethyl)phenyl)-5H-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-4-ium-5-uide

8-(4-trifluoromethylphenyl)-1,7-dimethyl-3,5-bis(4-methoxystyryl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

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