2-Iodo-4-dimethylaminopyridine

Base Information

• Chemical Name: 2-Iodo-4-dimethylaminopyridine
• CAS No.: 396092-83-4
• Molecular Formula: C7H9IN2
• Molecular Weight: 248.066
• DSSTox Substance ID: DTXSID90454730
• Nikkaji Number: J1.696.297J
• Wikidata: Q82276424
• Mol file: 396092-83-4.mol

Synonyms:2-IODO-4-DIMETHYLAMINOPYRIDINE;396092-83-4;2-IODO-N,N-DIMETHYLPYRIDIN-4-AMINE;SCHEMBL1010454;DTXSID90454730;HCLURSXUMBFJEH-UHFFFAOYSA-N;2-Iodo-N,N-dimethylpyridine-4-amine;FT-0768660;J-400307

Chemical Property of 2-Iodo-4-dimethylaminopyridine

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 297.736oC at 760 mmHg
• Flash Point: 133.866oC
• PSA: 16.13000
• Density: 1.738g/cm3
• LogP: 1.75220
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 247.98105
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

2-Iodo-4-dimethylaminopyridine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC(=NC=C1)I

Technology Process of 2-Iodo-4-dimethylaminopyridine

There total 4 articles about 2-Iodo-4-dimethylaminopyridine 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: 72.0%

dmap (1122-58-3) → (2-iodo-pyridin-4-yl)-dimethyl-amine (396092-83-4)

Guidance literature:

dmap; With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

With iodine; In tetrahydrofuran; at -30 - 25 ℃; Inert atmosphere;

DOI:10.1021/ol200563j

Reference yield:

2,4-diiodo-pyridine (83674-71-9) + dimethyl amine (124-40-3) → (4-iodo-pyridin-2-yl)-dimethyl-amine (1062609-45-3) + (2-iodo-pyridin-4-yl)-dimethyl-amine (396092-83-4)

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 10.5h; Microwave irradiation;

Reference yield:

2,4-dichloropyridine (26452-80-2) → (4-iodo-pyridin-2-yl)-dimethyl-amine (1062609-45-3) + (2-iodo-pyridin-4-yl)-dimethyl-amine (396092-83-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride; acetyl chloride / acetonitrile; mineral oil / Reflux

2: N,N-dimethyl-formamide / 10.5 h / 120 °C / Microwave irradiation

With sodium hydride; acetyl chloride; In N,N-dimethyl-formamide; acetonitrile; mineral oil;

upstream raw materials:

dmap

2,4-diiodo-pyridine

dimethyl amine

2,4-dichloropyridine

Downstream raw materials:

N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine

C₂₇H₄₂N₄O₃S

C₂₃H₃₈N₄O₃S

C₂₃H₃₆N₄O₃S

Refernces

• 1、 -. "SUBSTITUTED TRIAZOLES AND THEIR USE FOR TREATMENT AND/OR PREVENTION NEUROLOGICAL AND PSYCHIATRIC DISORDERS". Page/Page column 53. . Retrieved 2013/07/31.
• 2、 Jaric, Milica,Haag, Benjamin A.,Manolikakes, Sophia M.,Knochel, Paul. "Selective and multiple functionalization of pyridines and alkaloids via Mg- and Zn-organometallic intermediates". supporting information; experimental part. p. 2306 - 2309. Retrieved 2011/06/26.