METHYL 2,5-DIMETHYLPYRROLE-3-CARBOXYLATE

Base Information

• Chemical Name: METHYL 2,5-DIMETHYLPYRROLE-3-CARBOXYLATE
• CAS No.: 69687-80-5
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.181
• Hs Code.: 2933990090
• Mol file: 69687-80-5.mol

Synonyms:Methyl2,5-dimethyl-1H-pyrrole-3-carboxylate;Methyl 2,5-dimethylpyrrole-3-carboxylate;

Chemical Property of METHYL 2,5-DIMETHYLPYRROLE-3-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 0.00163mmHg at 25°C
• Melting Point: 115 °C
• Refractive Index: 1.521
• Boiling Point: 294.3 °C at 760 mmHg
• PKA: 16.87±0.50(Predicted)
• Flash Point: 131.8 °C
• PSA: 42.09000
• Density: 1.108 g/cm³
• LogP: 1.41810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

99%, ^*data from raw suppliers

Methyl2,5-Dimethyl-1H-pyrrole-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: 36/37/38
• Safety Statements: 26-37

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 2,5-DIMETHYLPYRROLE-3-CARBOXYLATE

There total 11 articles about METHYL 2,5-DIMETHYLPYRROLE-3-CARBOXYLATE 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: 57.0%

(E)-3-(2-Hydroxy-1-methyl-ethylamino)-but-2-enoic acid methyl ester → methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (69687-80-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,4,6-trimethylphenyl bromide; potassium carbonate; In N,N-dimethyl-formamide; at 150 ℃; for 3.5h;

DOI:10.1016/S0040-4039(96)02134-X

Reference yield: 20.0%

acetoacetic acid methyl ester (105-45-3) + chloroacetone (78-95-5) → methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (69687-80-5)

Guidance literature:

With ammonium hydroxide; at 20 ℃; for 17h;

DOI:10.1021/ja7102422

Reference yield:

C8H13NO3 (1286715-92-1) → methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate (69687-80-5) + methyl 2,4-dimethyl-1H-pyrrole 3-carboxylate (52459-90-2)

Guidance literature:

With sodium tetrahydroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 25 - 75 ℃; for 21h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo200061b

upstream raw materials:

diazomethane

2,5-dimethyl-1H-pyrrole-3-carboxylic acid

acetoacetic acid methyl ester

chloroacetone

Downstream raw materials:

methyl 4-(2-((4-fluorophenyl)methyl)benzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

methyl 4-<2-(2,5-difluorobenzyl)benzoyl>-2,5-dimethylpyrrole-3-carboxylate

4-(2-chloromethylbenzoyl)pyrrole

methyl 4-(2-iodobenzoyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate

Refernces

• 1、 Wang, Heng-Yen,Mueller, Daniel S.,Sachwani, Rachna M.,Kapadia, Rachel,Londino, Hannah N.,Anderson, Laura L.. "Regioselective synthesis of 2,3,4- or 2,3,5-trisubstituted pyrroles via [3,3] or [1,3] rearrangements of O-vinyl oximes". supporting information; experimental part. p. 3203 - 3221. Retrieved 2011/06/24.
• 2、 Aoyagi, Yutaka,Mizusaki, Toshihiko,Ohta, Akihiro. "Facile and efficient synthesis of pyrroles and indoles via palladium-catalyzed oxidation of hydroxy-enamines and -amines". . p. 9203 - 9206. Retrieved 2007/10/03.