308366-26-9

Basic information

• Product Name: 1,2-Ethanediol,1-(2-pyridinyl)-,(1R)-(9CI)
• Synonyms: 1,2-Ethanediol,1-(2-pyridinyl)-,(1R)-(9CI)
• CAS NO: 308366-26-9
• Molecular Formula: C7H9NO2
• Molecular Weight: 139.15
• Product Categories: PYRIDINE
• Mol File: 308366-26-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Ethanediol,1-(2-pyridinyl)-,(1R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol,1-(2-pyridinyl)-,(1R)-(9CI)(308366-26-9)
• EPA Substance Registry System: 1,2-Ethanediol,1-(2-pyridinyl)-,(1R)-(9CI)(308366-26-9)

Safety Data

• Hazardous Substances Data: 308366-26-9(Hazardous Substances Data)

Usage

Chirality

Chiral molecule

Stereocenter

Single stereocenter (1R)

Enantiomers

Exists in two mirror-image forms

Applications

a. Building block or intermediate in the synthesis of pharmaceuticals
b. Used in the synthesis of other organic compounds
c. Potential applications in medicinal chemistry and drug discovery

Handling considerations

Requires careful handling to avoid enantiomeric contamination

Upstream product

• 89791-91-3 2-hydroxy-2-(pyridin-2-yl)acetic acid 
• 55967-94-7 2-oxiranylpyridine 
• 162085-26-9 (S)-4-(2-pyridyl)-2,2-dimethyl-1,3-dioxolane 
• 100-69-6 2-vinylpyridine 

Downstream Products

• 160821-26-1 (R)-2-(1-amino-2-hydroxyethyl)pyridine 
• 95836-52-5 2-(α-hydroxyacetyl)pyridine 

Relevant articles and documents

2-Acetylpyridine thiosemicarbazones XI: 2-(α-hydroxyacetyl)pyridine thiosemicarbazones as antimalarial and antibacterial agents

A series of 2-(α-hydroxyacetyl)pyridine thiosemicarbazones was synthesized as potential antimalarial and antibacterial agents. Their synthesis was achieved by the condensation of N4-mono- or N4,N4-disubstituted thiosemicarbazides with 2-(α-hydroxyacetyl)pyridine. The latter was prepared by selective bromide oxidation of (2-pyridinyl)-1,2-ethanediol. The new compounds show potent inhibitory activity against penicillin-sensitive as well as penicillin-resistant Neisseria gonorrhoeae (MIC, 0.5-0.004 μg/mL), against Neisseria meningitidis (MIC, 0.5-0.032 μg/mL), and Staphylococcus aureus (MIC, 0.5-2 μg/mL). Good in vitro antimalarial effects against Plasmodium falciparum (Smith strain; ID50, 6.7-38 ng/mL) were observed in most of these new agents, but only 3 of 12 compounds exhibit moderate in vivo activity against Plasmodium berghei. These new agents appear to be less toxic to the host and more water soluble than the corresponding 2-acetylpyridine thiosemicarbazones.

Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides

To access the key Ile-Hpa pseudodipeptide motif in hibispeptins, a series of bidentate carboxamide-based auxiliary groups have been explored to facilitate the palladium-catalyzed arylation of unactivated γ-C(sp3)-H bonds of Ile precursor with a

Microbiological transformations. 47. A step toward a green chemistry preparation of enantiopure (S)-2-, -3-, and -4-pyridyloxirane via an epoxide hydrolase catalyzed kinetic resolution

The biocatalyzed hydrolytic kinetic resolution of 2-, 3-, and 4-pyridyloxirane by the Aspergillus niger epoxide hydrolase (EH) has been explored. This was used to perform a gram scale preparation of these epoxides of (S) absolute configuration using a process performed at a concentration as high as 10 g/L (82 mM). All three epoxides have been obtained in a nearly enantiopure form (ee > 98%). Interestingly, it was shown that this biotransformation could be achieved using plain water instead of buffer solution, an important improvement as far as downstream processing of an eventual industrial process is concerned. Neither of these substrates could be obtained in reasonable enantiomeric purity and yield using the nowadays most efficient metal-based catalysts.