2-Methyl-3-amylpyrrole

Base Information

• Chemical Name: 2-Methyl-3-amylpyrrole
• CAS No.: 18320-91-7
• Molecular Formula: C10H17 N
• Molecular Weight: 151.252
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90171399
• Nikkaji Number: J2.180.440A
• Wikidata: Q83041479
• Mol file: 18320-91-7.mol

Synonyms:2-methyl-3-amylpyrrole;2-methyl-3-n-amylpyrrole;2-methyl-3-pentylpyrrole

Chemical Property of 2-Methyl-3-amylpyrrole

Chemical Property:

• Vapor Pressure: 0.0637mmHg at 25°C
• Boiling Point: 238.9°C at 760 mmHg
• Flash Point: 94.3°C
• PSA: 15.79000
• Density: 0.909g/cm³
• LogP: 3.05580
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 151.136099547
• Heavy Atom Count: 11
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=C(NC=C1)C

Technology Process of 2-Methyl-3-amylpyrrole

There total 11 articles about 2-Methyl-3-amylpyrrole 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: 79.0%

isopropyl 5-methyl-4-pentyl-1H-pyrrole-2-carboxylate → 2-methyl-3-pentyl-1H-pyrrole (18320-91-7)

Guidance literature:

With sodium hydroxide; In 1,2-dimethoxyethane; at 160 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.1c00748

Reference yield: 43.0%

octan-2-one oxime (7207-49-0) + 1,2-dichloro-ethane (107-06-2,52399-93-6) → 2-methyl-3-pentyl-1H-pyrrole (18320-91-7) + 2-methyl-3-pentyl-1-vinyl-pyrrole (64222-37-3) + Octan-2-one O-{2-[1-methyl-hept-(E)-ylideneaminooxy]-ethyl}-oxime (97421-51-7)

Guidance literature:

at 120 - 125 ℃; for 1.5h; Product distribution; var. time, var. temperatures;

DOI:10.1007/BF00505898

Reference yield: 42.0%

octan-2-one oxime (7207-49-0) + 1,2-dichloro-ethane (107-06-2,52399-93-6) → 2-methyl-3-pentyl-1H-pyrrole (18320-91-7) + 2-methyl-3-pentyl-1-vinyl-pyrrole (64222-37-3)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 120 - 125 ℃; for 1.5h; Title compound not separated from byproducts;

DOI:10.1007/BF00505898

upstream raw materials:

5-methyl-4-pentyl-pyrrole-2-carboxylic acid ethyl ester

ethyl 5-methyl-4-pentanoyl-1H-pyrrole-2-carboxylate

octan-2-one oxime

1,2-dichloro-ethane

Downstream raw materials:

5-methyl-4-pentyl-1H-pyrrole-2-carbaldehyde

prodigiosin

2-methyl-3-pentylprodigiosene

4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole

Refernces

• 1、 Kancharla, Papireddy,Li, Yuexin,Yeluguri, Monish,Dodean, Rozalia A.,Reynolds, Kevin A.,Kelly, Jane X.. "Total Synthesis and Antimalarial Activity of 2-(p-Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria". . p. 8739 - 8754. Retrieved 2021/06/30.
• 2、 Boger, Dale L.,Patel, Mona. "Total Synthesis of Prodigiosin, Prodigiosene, and Desmethoxyprodigiosin: Diels-Adler Reactions of Heterocyclic Azadienes and Development of an Effective Palladium(II)-Promoted 2,2'-Bipyrrole Coupling Procedure". . p. 1405 - 1415. Retrieved 2007/10/02.