15905-16-5

Basic information

• Product Name: DIPICOLINIC ACID N-OXIDE
• Synonyms: DIPICOLINIC ACID N-OXIDE;PYRIDINE-2,6-DICARBOXYLIC ACID N-OXIDE;pyridine-2,6-dicarboxylic acid 1-oxide;2,6-Dicarboxypyridine 1-oxide;2,6-Pyridinedicarboxylic acid 1-oxide;1-oxidopyridin-1-ium-2,6-dicarboxylic acid;2,6-Pyridinedicarboxylic acid N-oxide
• CAS NO: 15905-16-5
• Molecular Formula: C₇H₅NO₅
• Molecular Weight: 183.12
• EINECS: 240-043-4
• Mol File: 15905-16-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 155-157 °C
• Boiling Point: 644.8 °C at 760 mmHg
• Flash Point: 343.7 °C
• Appearance: /
• Density: 1.6 g/cm³
• PKA: 0.97±0.50(Predicted)
• CAS DataBase Reference: DIPICOLINIC ACID N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPICOLINIC ACID N-OXIDE(15905-16-5)
• EPA Substance Registry System: DIPICOLINIC ACID N-OXIDE(15905-16-5)

Safety Data

• Hazardous Substances Data: 15905-16-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 1569, 1959 DOI: 10.1021/jo01092a605

InChI:InChI=1/C7H5NO5/c9-6(10)4-2-1-3-5(7(11)12)8(4)13/h1-4H,(H-,9,10,11,12)/p+1

Upstream product

• 499-83-2 Pyridine-2,6-dicarboxylic acid 

Downstream Products

• 866412-31-9 [Zn(pyridine-2,6-dicarboxylate)(1,4-bis(imidazol-1-ylmethyl)benzene)](n) 
• 71022-75-8 4-chloropyridine-2,6-dicarbonyl dichloride 

Relevant articles and documents

-

-

Imidazole derivative used as antiviral agent and use thereof in preparation of medicament

Disclosed are an antiviral compound and a use thereof in the preparation of a medicament for the treatment of virus infections. Specifically, the present invention relates an imidazole derivative for treating respiratory syncytial virus infection.

Novel chiral pyridine N-oxide ligands and their application in the enantioselective catalytic reduction of ketones and the addition of diethylzinc to aldehydes

Starting from picolinic acids 3 and 4, the amino acid-derived 2- aminoacylpyridine N-oxides 1a,c-e and 2,6-bis(aminoacyl)pyridine N-oxides 2b- e can be prepared in two steps by the coupling of picolinic acid N-oxides 5 and 6 under Appel conditions with the corresponding L-amino acid ester or (1R,2S)-norephedrine. Compounds 1 and 2 were used as chiral ligands in two different asymmetric catalyses. In the catalytic addition of diethylzinc to benzaldehyde 11, low enantioselectivities (2-29percent ee) were obtained regardless of the amino acid moiety. However, the corresponding 2,6- bis(aminoacyl)pyridines 7 and 8 led to increased ee values (55percent ee). In the catalytic reduction of ketones 9a-c to alcohols 10a-c low enantioselectivities were observed for alanine-, valine-, and leucine-derived N-oxides 1a,c and 2b,c. An increase of selectivity was observed for bismethionine ligand 2d (32-38percent ee) relative to that of monomethionine ligand 1d (7-16percent ee). However, mononorephedrine ligand 1e (≤ 64percent ee) and the corresponding bis-norephedrine ligand 2e (≤ 51percent ee) displayed the highest selectivities. The influence of the N-oxide moiety on the enantioselectivity was demonstrated by the observation that 2,6-bis(aminoacyl)pyridines 7 and 8 gave much lower selectivities than the corresponding pyridine N-oxides 2d and e.