1,2-Ethanediol, 1,2-bis(6-methylpyridyl)-

Base Information

• Chemical Name: 1,2-Ethanediol, 1,2-bis(6-methylpyridyl)-
• CAS No.: 6630-20-2
• Molecular Formula: C14H16 N2 O2
• Molecular Weight: 244.293
• European Community (EC) Number: 229-621-7
• NSC Number: 60034
• DSSTox Substance ID: DTXSID00984856
• Nikkaji Number: J298.021E
• ChEMBL ID: CHEMBL1887098
• Mol file: 6630-20-2.mol

Synonyms:6630-20-2;MLS002693268;1,2-Ethanediol, 1,2-bis(6-methylpyridyl)-;1,2-bis(6-methylpyridin-2-yl)ethane-1,2-diol;NSC60034;EINECS 229-621-7;1,2-diol;CHEMBL1887098;SCHEMBL14577729;DTXSID00984856;HMS3080J20;NSC 60034;NSC-60034;AKOS024323784;1,2-Bis(6-methyl-2-pyridyl)ethanediol;SMR001559227;1,2-Bis(6-methyl-2-pyridyl)-1,2-ethanediol

Chemical Property of 1,2-Ethanediol, 1,2-bis(6-methylpyridyl)-

Chemical Property:

• Vapor Pressure: 3.69E-07mmHg at 25°C
• Boiling Point: 401.3°C at 760 mmHg
• Flash Point: 196.5°C
• PSA: 66.24000
• Density: 1.23g/cm³
• LogP: 1.86040
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 236

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC(=CC=C1)C(C(C2=CC=CC(=N2)C)O)O

Technology Process of 1,2-Ethanediol, 1,2-bis(6-methylpyridyl)-

There total 2 articles about 1,2-Ethanediol, 1,2-bis(6-methylpyridyl)- 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:

2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)]ethan-1-one (7252-50-8) → 1,2-bis-(6-methyl-pyridin-2-yl)-ethane-1,2-diol (6630-20-2)

Guidance literature:

With hydrogenchloride; magnesium hydrosilicate; palladium; Hydrogenation;

Reference yield:

2,6-dimethylpyridine (108-48-5) → 1,2-bis-(6-methyl-pyridin-2-yl)-ethane-1,2-diol (6630-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: air; steam; V₂O₅/MoO₃/silica gel / 400 °C

2: palladium/ asbestos; aq.-ethanolic HCl / Hydrogenation

With hydrogenchloride; air; magnesium hydrosilicate; steam; vanadia; silica gel; palladium; molybdenum(VI) oxide;

upstream raw materials:

2-hydroxy-[1,2-bis(6-methylpyridin-2-yl)]ethan-1-one

2,6-dimethylpyridine

Refernces

Lithiated 4-isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one: A chiral formyl anion equivalent for enantioselective preparations of 1,2-diols, 2-amino alcohols, 2-hydroxy esters, and 4-hydroxy-2-alkenoates

10.1021/jo0155254

The study focuses on the synthesis and application of a chiral formyl anion equivalent, specifically lithiated 4-isopropyl-3-(methylthiomethyl)-5,5-diphenyloxazolidin-2-one, for the enantioselective preparation of various chiral compounds, including 1,2-diols, 2-amino alcohols, 2-hydroxy esters, and 4-hydroxy-2-alkenoates. The researchers utilized a series of chemical reactions involving reagents such as BuLi (butyllithium) for lithiation, aldehydes, ketones, and imines for addition reactions, as well as protecting groups like MOMCl (chloromethyl methyl ether) and BnBr (benzyl bromide) for in situ protection of the formed OH groups. The purpose of these chemicals was to achieve selective formation of chiral centers in the target molecules, which are valuable in the synthesis of complex organic molecules and pharmaceuticals. The study also explored the scope and limitations of this new transformation and compared the performance of the chiral auxiliary used with other oxazolidinones of different substitution patterns.

Hydroxyl-directed reductive cleavage of 3-oxetanols as an entry to diastereomerically pure 1,2-diols

10.1021/jo952235c

The research describes a method for the hydroxyl-directed reductive cleavage of 3-oxetanols to synthesize diastereomerically pure 1,2-diols, which is of significant interest in organic synthesis due to the challenge of reversing the polarity of a carbonyl compound from an a1 to a d1 synthon. The researchers utilized a photocycloaddition of silyl enol ethers to aromatic aldehydes, resulting in the formation of oxetanes, which were then subjected to a selective SN2-type ring opening. The key reagents in this process included lithium tris(tert-butoxy)aluminum hydride (LTBA), triethylborane (BEt3), and tetrahydropyran (THP), as well as potassium carbonate (K2CO3) and lithium aluminum hydride (LiAlH4). The study concluded that the methodology offers a more stereoselective approach to 1,2-diols bearing a secondary and a tertiary center compared to conventional methods, with the overall yield of diastereomerically pure diol ranging between 36 and 59% for the three-step procedure. The researchers are further investigating the scope of these hydroxyl-directed ring-opening reactions.

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