Pyridine, 2-(1,3-dioxolan-2-yl)-

Base Information

• Chemical Name: Pyridine, 2-(1,3-dioxolan-2-yl)-
• CAS No.: 5693-54-9
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• NSC Number: 111055
• UNII: YB42JFC1XN
• DSSTox Substance ID: DTXSID1063980
• Nikkaji Number: J421.779I
• Wikidata: Q81991143
• Mol file: 5693-54-9.mol

Synonyms:2-(1,3-Dioxolan-2-yl)pyridine;5693-54-9;Pyridine, 2-(1,3-dioxolan-2-yl)-;Picolinaldehyde, cyclic ethylene acetal;2-(1,3-Dioxalan-2-yl)pyridine;YB42JFC1XN;Pyridine-2-carbaldehyde ethylene acetal;2-Pyridinyl-1,3-dioxolane;2-Pyridinecarboxaldehyde, cyclic 1,2-ethanediyl acetal;2-(2-Pyridyl)-1,3-dioxolane;NSC 111055;NSC-111055;UNII-YB42JFC1XN;1.3-dioxolan-2-yl-pyridine;(2-pyridyl)-1,3-dioxolane;Pyridine,3-dioxolan-2-yl)-;SCHEMBL6982003;DTXSID1063980;2-(1.3-dioxolan-2-yl)pyridine;2-(1,3-dioxolan-2-yl)-pyridine;MFCD00234423;NSC111055;AKOS006239788;pyridine-2-carboxaldehyde ethylene acetal;2-Pyridinecarboxaldehyde,2-ethanediyl acetal;D84589

Chemical Property of Pyridine, 2-(1,3-dioxolan-2-yl)-

Chemical Property:

• Vapor Pressure: 0.0165mmHg at 25°C
• Boiling Point: 263.8°C at 760 mmHg
• Flash Point: 96.6°C
• PSA: 31.35000
• Density: 1.178g/cm³
• LogP: 1.12700
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 123

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC(O1)C2=CC=CC=N2

Technology Process of Pyridine, 2-(1,3-dioxolan-2-yl)-

There total 6 articles about Pyridine, 2-(1,3-dioxolan-2-yl)- 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: 94.0%

pyridine-2-carbaldehyde (1121-60-4) + ethylene glycol (107-21-1) → 2-(1,3-dioxolan-2-yl)pyridine (5693-54-9)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating; Dean-Stark apparatus;

DOI:10.1002/jhet.5570400212

Reference yield: 75.0%

pyridine-2-carbaldehyde (1121-60-4) + 2-chloro-ethanol (107-07-3) → 2-(1,3-dioxolan-2-yl)pyridine (5693-54-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at -60 ℃; for 1.5h;

DOI:10.1021/ol0613113

Reference yield: 73.0%

1,3-DIOXOLANE (646-06-0) + C15H14N2O3 → 2-(1,3-dioxolan-2-yl)pyridine (5693-54-9)

Guidance literature:

With dibenzoyl peroxide; at 130 ℃; for 10h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201403479

upstream raw materials:

pyridine-2-carbaldehyde

ethylene glycol

1,3-DIOXOLANE

pyridine

Downstream raw materials:

1-(2,5-dichloro-benzyl)-2-[1,3]dioxolan-2-yl-pyridinium; bromide

1-(4-carboxy-benzyl)-2-[1,3]dioxolan-2-yl-pyridinium; bromide

1-(2,5-diacetoxy-benzyl)-2-[1,3]dioxolan-2-yl-pyridinium; bromide

1-(2,3-diacetoxy-benzyl)-2-[1,3]dioxolan-2-yl-pyridinium; bromide

Refernces

• 1、 Hobson, Stephen T.,Boecker, Joseph D.,Gifford, James H.,Nohe, Tara L.,Wierks, Carl H.. "Synthesis and unusual stability of pyridine and N-methyl pyridinium 1,3-dioxolanes". . p. 277 - 282. Retrieved 2003.
• 2、 Dong, Lefeng,Kong, Yijin,Li, Zhong,Liang, Junqing,Qian, Feng,Shao, Xusheng,Wang, Mingxia,Xu, Xiaoyong. "A bench-stable reagent for C-4 selective deuteriodifluoromethylation of azines". supporting information. . Retrieved 2022/03/16.
• 3、 Fang, Lei,Chen, Liangshun,Yu, Jianjun,Wang, Limin. "Benzoyl peroxide promoted radical ortho-alkylation of nitrogen heteroaromatics with simple alkanes and alcohols". supporting information. p. 1910 - 1914. Retrieved 2015/03/18.