Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-carboxylate

Base Information

• Chemical Name: Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-carboxylate
• CAS No.: 372520-85-9
• Molecular Formula: C₂₀H₁₇Br₂N₃O₂
• Molecular Weight: 491.182
• DSSTox Substance ID: DTXSID30376422
• Nikkaji Number: J1.561.830B
• Wikidata: Q82165353
• Mol file: 372520-85-9.mol

Synonyms:372520-85-9;6,6''-Bis(bromomethyl)-[2,2':6',2''-terpyridine]-4'-carboxylic acid ethyl ester;Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-carboxylate;Ethyl 6,6''-bis(bromomethyl)-[2,2':6',2''-terpyridine]-4'-carboxylate;Ethyl 6,6''-bis(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate;DTXSID30376422;FT-0620838;Ethyl6,6''-bis(bromomethyl)-[2,2':6',2''-terpyridine]-4'-carboxylate;6,6''-Bis(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester;6,6-BIS(BROMOMETHYL)-[2,2:6,2-TERPYRIDINE]-4-CARBOXYLICACIDETHYLESTER;Ethyl 1~6~,3~6~-bis(bromomethyl)[1~2~,2~2~:2~6~,3~2~-terpyridine]-2~4~-carboxylate

Chemical Property of Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-carboxylate

Chemical Property:

• Boiling Point: 569.7oC at 760 mmHg
• PKA: 1.29±0.46(Predicted)
• Flash Point: 298.3oC
• PSA: 64.97000
• Density: 1.568g/cm3
• LogP: 5.17210
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 490.96670
• Heavy Atom Count: 27
• Complexity: 450

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

6,6''-BIS(BROMOMETHYL)-[2,2':6',2''-TERPYRIDINE]-4'-CARBOXYLIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=NC(=C1)C2=CC=CC(=N2)CBr)C3=CC=CC(=N3)CBr

Technology Process of Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-carboxylate

There total 6 articles about Ethyl 2,6-bis[6-(bromomethyl)pyridin-2-yl]pyridine-4-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: 27.0%

6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester (372520-84-8) → ethyl 6,6''-bis-(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate (372520-85-9)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In benzene; for 3h; Heating; irradiation;

DOI:10.1016/S0040-4039(01)01195-9

Reference yield:

2-methyl-6-(tributylstannyl)pyridine (259807-95-9) → ethyl 6,6''-bis-(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate (372520-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Pd(PPh₃)4 / toluene / 72 h / Heating

2: NBS; AIBN / benzene / 3 h / Heating; irradiation

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; benzene;

DOI:10.1021/jo0480242

Reference yield:

2,6-dichloroisonicotinic acid ethyl ester (1604-14-4) → ethyl 6,6''-bis-(bromomethyl)-2,2':6',2''-terpyridine-4'-carboxylate (372520-85-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / Pd(PPh₃)4 / toluene / 72 h / Heating

2: NBS; AIBN / benzene / 3 h / Heating; irradiation

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; benzene;

DOI:10.1021/jo0480242

upstream raw materials:

6,6''-dimethyl-2,2':6',2''-terpyridine-4'-carboxylic acid ethyl ester

2,6-dichloroisonicotinic acid ethyl ester

2-methyl-6-(tributylstannyl)pyridine

ethyl 2,6-dibromo-pyridine-4-carboxylate

Downstream raw materials:

C₃₂H₃₂N₆O₉

tetraethyl (4'-(p-aminophenoxy)methylene-2,2':6',2''-terpyridine-6,6''-diyl)bis(methylenenitrilo)tetrakis(acetate)