200614-58-0

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 176446-62-1 5-(4-methoxyphenyl)dipyrromethane 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1299466-65-1 3,5-diformyl-8-(methoxyphenyl)-4-bora-3a,4a-diaza-s-indacene 
• 1299466-66-2 3,5-diformyl-8-(3,4,5-trimethoxyphenyl)-4-bora-3a,4a-diaza-s-indacene 

Relevant academic research and scientific papers

Investigations on the directive effects of a single meso-substituent via nitration of 5,12,13,17,18-pentasubstituted porphyrins: Syntheses of conjugated β-nitroporphyrins

Vilsmeier formylation of 5-substituted 1,9-diunsubstituted dipyrromethanes afforded 1,9-diformyldipyrromethanes in good yields. Their MacDonald condensation with tetra-β-alkyldipyrromethanes produced 5,12,13,17,18-pentasubstituted porphyrins. A meso-electron-donating group, presumably acting by destabilizing the porphyrin a2u ground state, directs the nitrations to the meso-carbons. β-Nitration takes place on porphyrins bearing a meso-electron-withdrawing group. Unhindered β-nitro groups are shown to exert stronger electronic effects relative to meso-nitro groups by conjugating effectively with the porphyrin macrocycle.

α-/β-formylated boron-dipyrrin (BODIPY) dyes: Regioselective syntheses and photophysical properties

Formylation has been performed on pyrrole-unsubstituted dipyrromethanes 1 and boron-dipyrrin (BODIPY) dyes 4 based on a Vilsmeier-Haack reaction. It is highly regioselective and complementary and occurs exclusively at the α-and β-position, respectively, f

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.

Methods and intermediates for the synthesis of porphyrins

A method of making a porphyrin (I) is carried out by condensing (i) a bis(imino)dipyrromethane of Formula II: with (ii) a dipyrromethaneto produce a reaction product; then (b) optionally oxidizing said reaction product with an oxidizing agent; and then (c) optionally demetallating said reaction product to produce the porphyrin. Methods of making compounds of Formula II are also described.