3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate

Base Information

• Chemical Name: 3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate
• CAS No.: 92757-16-9
• Molecular Formula: C6H7 N3 O2
• Molecular Weight: 153.14
• Hs Code.: 2933399090
• European Community (EC) Number: 861-979-5
• DSSTox Substance ID: DTXSID30430553
• Mol file: 92757-16-9.mol

Synonyms:N-Hydroxy-1-oxy-nicotinamidine;92757-16-9;3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate;N'-hydroxy-1-oxidopyridin-1-ium-3-carboximidamide;(Z)-3-(N'-Hydroxycarbamimidoyl)pyridine 1-oxide;2102429-29-6;3-[amino(hydroxyimino)methyl]pyridinium-1-olate;starbld0043155;SCHEMBL1447051;DTXSID30430553;AKOS006229228;AKOS025403203;AS-31767;EN300-6488406;A920385

Chemical Property of 3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate

Chemical Property:

• Boiling Point: 424.9±37.0 °C(Predicted)
• PKA: 12.61±0.50(Predicted)
• PSA: 84.07000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 0.90990
• Solubility.: DMSO
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 153.053826475
• Heavy Atom Count: 11
• Complexity: 160

Purity/Quality:

99%min ^*data from raw suppliers

N-Hydroxy-1-oxy-nicotinamidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)[O-])C(=NO)N
• Isomeric SMILES: C1=CC(=C[N+](=C1)[O-])/C(=N/O)/N
• Uses: N-Hydroxy-1-oxy-nicotinamidine is an intermediate in the synthesis of rac-Arimoclomol Maleic Acid (A771275), which is a potential antidiabetic agent used for the treatment of insulin resistance.

Technology Process of 3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate

There total 3 articles about 3-(N'-hydroxycarbamimidoyl)pyridin-1-ium-1-olate 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: 97.0%

3-cyanopyridine N-oxide (14906-64-0) → nicotinamidoxime 1-oxide (92757-16-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In water; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00152-5

Reference yield: 91.0%

3-cyanopyridine N-oxide (14906-64-0) → (Z)-3-(N'-hydroxycarbamimidoyl)pyridine N-oxide (92757-16-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium hydrogencarbonate; In water; at 20 ℃; for 18h;

DOI:10.1039/c7ob02578e

Reference yield: 10.0%

3-cyano-1-methylpyridinium iodide (1004-16-6) → nicotinamide N-oxide (1986-81-8) + (Z)-3-(N'-hydroxycarbamimidoyl)pyridine N-oxide (92757-16-9) + 2-Amino-3-pyridincarbaldehyd-(E)-oxim-1-oxid

Guidance literature:

With hydroxylamine; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 80 ℃; for 2h;

DOI:10.1515/znb-2000-0514

upstream raw materials:

3-cyanopyridine N-oxide

3-cyano-1-methylpyridinium iodide

Downstream raw materials:

3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)pyridine 1-oxide

Refernces

• 1、 Atkinson, Benjamin N.,Woodward, Hannah L.,Sipthorp, James,Fish, Paul V.. "Regioselective and enantiospecific synthesis of the HSP co-inducer arimoclomol from chiral glycidyl derivatives". supporting information. p. 9794 - 9799. Retrieved 2017/12/12.
• 2、 -. "Pyridine-1-oxide derivative, and process for its transformation into pharmaceutically effective compounds". Page 3. . Retrieved 2010/02/05.