1299466-63-9

Basic information

• Product Name: 3,5-diformyl-8-tolyl-4-bora-3a,4a-diaza-s-indacene
• Synonyms: 3,5-diformyl-8-tolyl-4-bora-3a,4a-diaza-s-indacene
• CAS NO: 1299466-63-9
• Molecular Weight: 338.121
• Mol File: 1299466-63-9.mol

Chemical Properties

• CAS DataBase Reference: 3,5-diformyl-8-tolyl-4-bora-3a,4a-diaza-s-indacene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-diformyl-8-tolyl-4-bora-3a,4a-diaza-s-indacene(1299466-63-9)
• EPA Substance Registry System: 3,5-diformyl-8-tolyl-4-bora-3a,4a-diaza-s-indacene(1299466-63-9)

Safety Data

• Hazardous Substances Data: 1299466-63-9(Hazardous Substances Data)

Upstream product

• 1299466-62-8 1,9-diformyl-meso-tolyl dipyrromethane 
• 109-63-7 trifluoroborane diethyl ether 
• 1618110-42-1 C₂₈H₂₇BF₂N₆O₆ 
• 1618110-44-3 C₂₄H₁₇BF₂N₆O₅ 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 1542255-09-3 C₂₆H₂₃BF₂N₄O₂ 
• 1618110-41-0 C₃₀H₂₅BF₂N₆ 
• 1618110-43-2 C₂₆H₂₃BF₂N₆O₆ 
• 1618110-42-1 C₂₈H₂₇BF₂N₆O₆ 
• 1369332-63-7 3,5-bis(dipyrromethanyl)-8-(tolyl)-4-bora-3a,4a-diaza-s-indacene 

Relevant articles and documents

Boron-dipyrromethene based multi-anionic sensor and a specific cationic sensor for Fe3+

Symmetrical and unsymmetrical phenylhydrazone substituted boron-dipyrromethenes were synthesized by treating 3,5-diformyl boron-dipyrromethene with phenylhydrazine/2,4-dinitrophenylhydrazine in ethanol at reflux temperature. The X-ray structure of the unsymmetrical boron-dipyrromethene (BODIPY) was shown to have an almost extended planar orientation of BODIPY with 2,4-dinitrophenylhydrozone unit at the 3-position and ethyl acetal at the 5-position with small torsional angles. A strong absorption band at ～600 to 700 nm and a weak emission band at ～620 to 710 nm were observed for the phenylhydrazone substituted BODIPYs. The compounds showed interesting absorption properties in DMSO and DMF solvents compared to other solvents by shifting ～150 nm towards the red region. Anion binding studies indicated that the unsymmetrical phenylhydrazone substituted BODIPY could be applied as a sensor for F-, CH3COO- and H 2PO4- ions as confirmed by various spectroscopic studies. Furthermore, the unsymmetrical phenylhydrazone substituted BODIPY had the unique ability of acting as a two step fluorescence enhanced chemodosimetric sensor for Fe3+ ion. This journal is the Partner Organisations 2014.

3,5-diformylboron dipyrromethenes as fluorescent pH sensors

A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl3 in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone and then reacted with BF3·OEt2 to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the 1H and 19F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.