1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI)

Base Information

• Chemical Name: 1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI)
• CAS No.: 123892-37-5
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.137
• Mol file: 123892-37-5.mol

Synonyms:1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI)

Chemical Property of 1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI)

Chemical Property:

• Boiling Point: 267.2±32.0 °C(Predicted)
• PKA: -10.18±0.70(Predicted)
• PSA: 48.30000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 0.91510

Purity/Quality:

2-formyl-1H-Pyrrole-1-carboxylicacidmethylester 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI)

There total 1 articles about 1H-Pyrrole-1-carboxylic acid, 2-formyl-, methyl ester (9CI) 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: 36.0%

2-pyrrole aldehyde (1003-29-8,254729-95-8) + dimethyl dicarbonate (4525-33-1) → methyl 2-formyl-1H-pyrrole-1-carboxylate (123892-37-5)

Guidance literature:

With dmap; In acetonitrile;

DOI:10.1002/1099-0690(200012)2000:23<3909::AID-EJOC3909>3.0.CO;2-R

Reference yield:

methyl 2-formyl-1H-pyrrole-1-carboxylate (123892-37-5) → 8-benzoyl-3α-benzyloxy-1-(1',3'-dioxolan-2'-yl)-2α,4α-dimethyl-8-azabicyclo[3.2.1]oct-6-ene

Guidance literature:

Multi-step reaction with 6 steps

1: 69 percent / p-toluenesulfonic acid / benzene / Heating

2: 61 percent / diethylzinc / toluene; hexane

3: 99 percent / DIBAL-H / toluene / -78 - -40 °C

4: 97 percent / sodium hydride / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

5: 52 percent / trimethylsilyl iodide / CH₂Cl₂

6: 98 percent / triethylamine / tetrahydrofuran / 2 h

With trimethylsilyl iodide; diethylzinc; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/1099-0690(200012)2000:23<3909::AID-EJOC3909>3.0.CO;2-R

Reference yield:

methyl 2-formyl-1H-pyrrole-1-carboxylate (123892-37-5) → methyl 3α-benzyloxy-1-carboxyaldehyde-2α,4α-dimethyl-8-azabicyclo[3.2.1]oct-6-ene-8-carboxylate

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / p-toluenesulfonic acid / benzene / Heating

2: 61 percent / diethylzinc / toluene; hexane

3: 99 percent / DIBAL-H / toluene / -78 - -40 °C

4: 97 percent / sodium hydride / tetrahydrofuran; dimethylformamide / 24 h / 20 °C

5: 98 percent / formic acid; water / 4 h / 20 °C

With formic acid; water; diethylzinc; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/1099-0690(200012)2000:23<3909::AID-EJOC3909>3.0.CO;2-R

upstream raw materials:

2-pyrrole aldehyde

dimethyl dicarbonate

Refernces