27226-49-9

Usage

Molecular Structure

1H-Pyrrole-2-carboxylic acid, 5,5'-methylenebis[3,4-dimethylconsists of a pyrrole ring with a carboxylic acid group (-COOH) attached to the 2 position, and two methyl groups (-CH3) attached to the 3 and 4 positions. The 5,5'-methylenebis group (-CH2-) links two separate pyrrole rings together.

Classification

It is an organic compound belonging to the pyrrole family.

Functional Groups

The main functional groups present in 1H-Pyrrole-2-carboxylic acid, 5,5'-methylenebis[3,4-dimethyl- are the pyrrole ring, carboxylic acid group (-COOH), and methyl groups (-CH3).

Reactivity

The compound is known for its unique reactivity due to the presence of the pyrrole ring and the 5,5'-methylenebis group, making it a versatile building block in organic synthesis.

Applications

It is commonly used in the synthesis of various organic compounds and pharmaceuticals, as well as a building block for creating more complex molecules in the field of organic chemistry.

Physical State

The compound is likely a solid at room temperature, as most organic compounds with similar structures are.

Solubility

The compound may be soluble in organic solvents such as ethanol, methanol, or dichloromethane, but its solubility in water may be limited due to the presence of the hydrophobic methyl groups.

Stability

The compound is likely stable under normal laboratory conditions, but it may be sensitive to strong acids, bases, or oxidizing agents due to the presence of the pyrrole ring and carboxylic acid group.

Upstream product

• 915-74-2 5,5'-bis-benzyloxycarbonyl-3,3',4,4'-tetramethyl-2,2'-dipyrromethane 
• 92578-75-1 5-bromomethyl-3,4-dimethyl-pyrrole-2-carboxylic acid benzyl ester 
• 4424-76-4 2-((benzyloxy)carbonyl)-3,4,5-trimethylpyrrole 
• 73018-13-0 5-bromomethyl-3,4-dimethyl-pyrrole-2-carboxylic acid ethyl ester 
• 2199-46-4 2-(ethoxycarbonyl)-3,4,5-trimethylpyrrole 
• 27226-48-8 3,4,3',4'-tetramethyl-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid diethyl ester 
• 65038-94-0 5-((acetoxy)methyl)-2-((benzyloxy)carbonyl)-3,4-dimethylpyrrole 

Downstream Products

• 1109-22-4 2,3,5,7,8,12,13,15,17,18-decamethyl-porphyrin 
• 184699-65-8 2,3,7,8,12,13,17,18-octamethyl-5,15-diethylporphyrin 

Relevant academic research and scientific papers

Synthesis and basic properties of 5-aza-2,3,7,8,12,13,17,18- octamethylporphyrin

5-Aza-2,3,7,8,12,13,17,18-octamethylporphyrin was synthesized and its basic properties were studied by means of spectrophotometric titration. Protonation of nitrogen atoms in the tetrapyrrolic macrocycle with the ethanolic sulfuric acid is found to be a two-step process. Corresponding ionization constants and the concentration ranges of existence of mono-and dicationic forms of the azaporphyrin under investigation are evaluated.

Synthesis and spectra of meso-dialkyl-β-octamethylporphyrins

Condensation of bis(3,4-dimethyl-2-pyrrolyl)methane or bis(5-carboxy-3,4-dimethyl-2-pyrrolyl)methane with unbranched aldehydes CnH2n+1CHO (n= 1-7) results in formation of 5,15-dialkyl-2,3,7,8,12,13,17,18-octamethylporphyrins. Zinc complexes of the porphyrins are obtained.

The Chemistry of Pyrrolic Compounds. LXX. The Synthesis of Model Porphyrins as an Aid to the Recognition of Chlorobium-Derived Petroporphyrins in the Julia Creek Oil Shale Deposit

In order to obtain evidence for the presence of Clorobium-derived petroporphyrins in the Julia Creek oil shales a range of simple porphyrins (10d-i) carrying the type of side chain characteristic of Chlorobium chlorophylls has been prepared for study by m

Novel Macrocycles from Metal-Catalyzed Oxidative Cyclizations of a,c-Biladiene Salts

From the metal-promoted oxidative cyclization of several 1,19-disubstituted a,c-biladiene dihydrobromide salts, a number of novel macrocycles were prepared.For example, the cyclization of 1,19-bis(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-a,c-biladiene dihydrobromide salt (10) with copper(II) acetate afforded copper(II) 20-((methoxycarbonyl)methyl)-1-(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-1,2a0-dihydroporphyrin (13) (39percent yield), which, upon demetalation, yielded the metal-free 20-((methoxycarbonyl)methyl)-1-(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-1,20-dihydroporphyrin (14) (48percent yield).With the substrate 19-((ethoxycarbonyl)methyl)-1-(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-a,c-biladiene dihydrobromide (15), the metal-catalyzed cyclization process produced copper(II) 20-(ethoxycarbonyl)-1-(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-1,20-dihydroporphyrin (18) (27percent yield) and copper(II) 20-(ethoxycarbonyl)-2-(2-(methoxycarbonyl)ethyl)-2,7,8,12,13,17,18-heptamethyl-3-methylidene-2,3-dihydroporphyrin (23) (19percent yield).Upon demetalation of the copper dihydroporphyrin 18, 20'-(ethoxycarbonyl)-20-(2-(methoxycarbonyl)ethyl)-2,3,7,8,12,13,17,18-octamethyl-20'-homoporphyrin (28) (16.5percent yield) was isolated; demetalation of copper(II) 20-(ethoxycarbonyl)-2-(2-(methoxycarbonyl)ethyl)-2,7,8,12,13,17,18-heptamethyl-3-methylidene-2,3-dihydroporphyrin (23) yielded the free base 20-(ethoxycarbonyl)-2-(2-(methoxycarbonyl)ethyl)-2,7,8,12,13,17,18-heptamethyl-3-methylidene-2,3-dihydroporphyrin (25) (24percent yield).Using chromium(III) hydroxy acetate as the oxidant (in place of copper(II)), 1,2,3,7,8,12,13,17,18-nonamethyl-1,20-dihydroprphyrin (5) (55-62percent) was obtained from the 1,2,3,7,8,12,13,17,18,19-decamethyl-a,c-biladiene salt 3.Mechanisms of macrocycle formation from a,c-biladiene salts, promoted by either copper(II) or chromium(III), appear to proceed via pathways closely resembling the electrochemical cyclization reaction of 1,19-dimethyl-a,c-biladiene salts.

Tetrapyrrole products from electrochemical cyclization of 1′,8′-disubstituted-a,c-biladiene salts

Anodic oxidation of 1′,8′-dimethyl- and other 1′,8′-disubstituted a.c-biladiene salts affords novel cyclized products. In addition to porphyrin, an unconjugated macrocyclic intermediate product resulting from oxidadve cyclizatfon during porphyrin synthesis is isolated, structurally identified, and characterized with regard to its spectroscopy, electrochemical behavior and chemical reactivity. The formation of a novel homoporphyrin from a 1′-ethoxycarbonylmethy-8′-(2-methoxycarbonylethyl)-a,c-biladiene salt is also briefly discussed.

Synthetic and Biosynthetic Studies of Porphyrins.Part10.Syntheses of Porphyrins with Acetic,Propionic,and Butyric Acid Side-chains for Biosynthetic Syudies.

In connection with studies of substrate specificity of uroporphyrinogen decarboxylase and coproporphyrinogen oxidase, enzymes in the heme and chlorophyll biosynthetic pathways,and heme oxygenase,an enzyme involved in the catabolism of hemes,we have synthesized a number of new porphyrins substituted with acetic,propionic,and butyric side-chains,using the a,c-biladiene route;one porphyrin was also prepared by the MacDonald pyrromethane approach.In one of the a,c-biladiene cyclizations,meso-chlorinated porphyrins were formed as minor by products,but this side-reaction was suppressed by carefully drying the copper(II) chloride used in this stage, or by use of copper(II) acetate as an alternative oxidant.

FORMYLATION OF PYRROLE DERIVATIVES

An improved procedure for the formylation of dipyrrylmethanes which are key intermediates in the synthesis of porphyrins is described.