4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Base Information

• Chemical Name: 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• CAS No.: 1363520-28-8
• Molecular Formula: C₃₁H₂₅BF₂N₂O₄
• Molecular Weight: 538.358

Synonyms:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Chemical Property of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Chemical Property:

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Technology Process of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

There total 5 articles about 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: 42.0%

(Z)-methyl-4-((5-(4-methoxyphenyl)-1H-pyrrole-2-yl) (5-(4-methoxyphenyl)-2H-pyrrole-2-ylidene)methyl)benzoate (1363512-35-9) → 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1363520-28-8)

Guidance literature:

(Z)-methyl-4-((5-(4-methoxyphenyl)-1H-pyrrole-2-yl) (5-(4-methoxyphenyl)-2H-pyrrole-2-ylidene)methyl)benzoate; With triethylamine; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c2cc30569k

Reference yield: 42.0%

(Z)-methyl 4-((5-(4-methoxyphenyl)-1H-pyrrole-2-yl)-(5-(4-methoxyphenyl)-2H-pyrrole-2-ylidene)methyl)benzoate (1364051-11-5) + boron trifluoride diethyl etherate (109-63-7) → 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1363520-28-8)

Guidance literature:

With triethylamine; In dichloromethane; (under N2); soln. of ligand and triethylamine in CH2Cl2 stirred at room temp. for 10 min, BF3*(CH3CH2)2O added dropwise over 10 min, stirred for24 h at room temp.; silica flash column chromy. with hexane/CH2Cl2;

DOI:10.1039/c2nj20786a

Reference yield:

2-(4-methoxyphenyl)-1-tosyl-1H-pyrrole (637354-46-2) → 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (1363520-28-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / ethanol / 3 h / Reflux

2.1: trifluoroacetic acid / ethyl acetate / 1 h / 20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C

4.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Inert atmosphere

4.2: 24 h / 20 °C / Inert atmosphere

With triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1039/c2cc30569k

upstream raw materials:

(Z)-methyl 4-((5-(4-methoxyphenyl)-1H-pyrrole-2-yl)-(5-(4-methoxyphenyl)-2H-pyrrole-2-ylidene)methyl)benzoate

boron trifluoride diethyl etherate

methyl 4-(bis(5-(4-methoxyphenyl)-1H-pyrrole-2-yl)methyl)-benzoate

(Z)-methyl-4-((5-(4-methoxyphenyl)-1H-pyrrole-2-yl) (5-(4-methoxyphenyl)-2H-pyrrole-2-ylidene)methyl)benzoate

Downstream raw materials:

Bodipy-CO₂H

Br-Bodipy-CO₂H

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