4-methoxy-2,2'-bipyrrole-5-carboxaldehyde

Base Information

• Chemical Name: 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde
• CAS No.: 10476-41-2
• Molecular Formula: C10H10 N2 O2
• Molecular Weight: 190.202
• Hs Code.: 2933990090
• Mol file: 10476-41-2.mol

Synonyms:[2,2'-Bipyrrole]-5-carboxaldehyde,4-methoxy- (6CI,7CI,8CI); 4-Methoxy[2,2'-bipyrrole]-5-carboxaldehyde; Tambjaminealdehyde

Chemical Property of 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde

Chemical Property:

• Boiling Point: 462.3°Cat760mmHg
• Flash Point: 233.4°C
• PSA: 57.88000
• Density: 1.293g/cm³
• LogP: 1.83090
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Methoxy-1H,1''H-2,2''-bipyrrole-5-carbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde

There total 30 articles about 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde 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: 95.0%

N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (960509-42-6) + N-boc-2-pyrroleboronic acid (135884-31-0) → 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (10476-41-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; toluene; at 100 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2006.02.035

Reference yield: 78.0%

N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine (960509-42-6) + pyrrole-2-boronic acid (763120-43-0) → 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (10476-41-2)

Guidance literature:

With sodium carbonate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; toluene; at 98 ℃;

DOI:10.1039/b719353j

Reference yield: 75.0%

N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)-methyl)-N-ethylethanamine (803712-71-2) + N-boc-2-pyrroleboronic acid (135884-31-0) → 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde (10476-41-2)

Guidance literature:

N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine; N-boc-2-pyrroleboronic acid; With sodium carbonate; triphenylphosphine; palladium diacetate; In 1,4-dioxane; water; toluene; at 100 ℃; for 3.5h;

With sodium methylate; In 1,4-dioxane; water; toluene; at 100 ℃; for 0.416667h; Further stages.;

DOI:10.1039/b801677a

upstream raw materials:

Tambjamine A

(Z)-N-((3-methoxy-5-(1H-pyrrol-2-yl)-2H-pyrrol-2-ylidene)methyl)-2-methylpropan-1-amine

C₁₇H₁₈N₄O₄S

4-methoxy-1H,1'H-[2,2']bipyrrolyl-5-carboxylic acid ethyl ester

Downstream raw materials:

prodigiosin

5'-[3-(2-cyclohexyl-ethyl)-5-propyl-1H-pyrrol-2-ylmethylene]-4'-methoxy-1H,5'H-[2,2']bipyrrolyl

5'-[3-(4-chloro-benzyl)-5-ethyl-1H-pyrrol-2-ylmethylene]-4'-methoxy-1H,5'H-[2,2']bipyrrolyl

5'-[3-(4-chloro-benzyl)-5-heptyl-1H-pyrrol-2-ylmethylene]-4'-methoxy-1H,5'H-[2,2']bipyrrolyl

Refernces

• 1、 Takaki, Mirelle,Freire, Vítor F.,Nicacio, Karen J.,Bertonha, Ariane F.,Nagashima, Nozomu,Sarpong, Richmond,Padula, Vinicius,Ferreira, Antonio G.,Berlinck, Roberto G. S.. "Metabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain". . p. 790 - 796. Retrieved 2021.
• 2、 Withall, David M.,Haynes, Stuart W.,Challis, Gregory L.. "Stereochemistry and Mechanism of Undecylprodigiosin Oxidative Carbocyclization to Streptorubin B by the Rieske Oxygenase RedG". . p. 7889 - 7897. Retrieved 2015.
• 3、 Wasserman, Harry H.,Xia, Mingde,Wang, Jianji,Petersen, Anders K.,Jorgensen, Michael,Power, Patricia,Parr, Jonathan. "Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs". . p. 7419 - 7425. Retrieved 2004.
• 4、 Dairi, Kenza,Tripathy, Sasmita,Attardo, Giorgio,Lavallée, Jean-Fran?ois. "Two-step synthesis of the bipyrrole precursor of prodigiosins". . p. 2605 - 2606. Retrieved 2006.