3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy

Base Information

• Chemical Name: 3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy
• CAS No.: 76893-32-8
• Molecular Formula: C9H15BrNO
• Molecular Weight: 233.128
• Mol file: 76893-32-8.mol

Synonyms:

Chemical Property of 3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy

Chemical Property:

• Vapor Pressure: 0.007mmHg at 25°C
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the production of spin labelled compounds

Technology Process of 3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy

There total 7 articles about 3-Bromomethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 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: 96.0%

(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl methanesulfonate (76893-27-1) → 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl (76893-32-8)

Guidance literature:

With lithium bromide; In acetone; for 2h; Reflux;

DOI:10.1021/acs.orglett.9b04216

Reference yield:

(2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol (55738-75-5) → 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl (76893-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Triethylamine / CH₂Cl₂ / 3 h / Ambient temperature

2: LiBr / acetone / 0.5 h / Heating

With triethylamine; lithium bromide; In dichloromethane; acetone;

DOI:10.1055/s-1980-29269

Reference yield:

2,2,6,6-Tetramethyl-4-piperidone (826-36-8) → 3-(bromomethyl)-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-oxyl (76893-32-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid / 20 °C

1.2: 16 h / 20 °C

2.1: methanol / 6 h / 0 - 20 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / diethyl ether / 1.5 h / 0 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 4.5 h / -78 - -50 °C

5.1: triethylamine / tetrahydrofuran / 1.17 h / 20 °C

6.1: lithium bromide / acetone / 2 h / Reflux

With diisobutylaluminium hydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; acetone;

DOI:10.1021/acs.orglett.9b04216

upstream raw materials:

2,5-dihydro-2,2,5,5-tetramethyl-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1H-pyrrol-1-yloxy

(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl methanesulfonate

(2,5-dihydro-2,2,5,5-tetramethyl-1-oxyl-1H-pyrrol-3-yl)methanol

2,2,6,6-Tetramethyl-4-piperidone

Downstream raw materials:

2-(3,4-dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl]-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-ylmethyl)-amino]-2-isopropyl-pentanenitrile radical

3-[(2-(3,4-dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl]-methylamino]-2-isopropyl-pentylamino)methyl]-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxyl radical

C₂₂H₃₀NO₅

4-(2-((2,5-dihydro-1-hydroxy-2,2,5,5-tetramethyl-1H-pyrrol-3-yl)methoxy)phenyl)morpholine hydrochloride

Refernces

• 1、 Hankovszky, H. O.,Hideg, K.,Lex, L.. "Nitroxyls; VII. Synthesis and Reactions of Highly Reactive 1-Oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-ylmethyl Sulfonates". . p. 914 - 916. Retrieved 2007/10/02.