5-Nitronicotinaldehyde

Base Information

• Chemical Name: 5-Nitronicotinaldehyde
• CAS No.: 87883-20-3
• Molecular Formula: C6H4N2O3
• Molecular Weight: 152.10800
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50519758
• Wikidata: Q82383180
• Mol file: 87883-20-3.mol

Synonyms:5-NITRONICOTINALDEHYDE;87883-20-3;5-NITROPYRIDINE-3-CARBALDEHYDE;SCHEMBL11725848;DTXSID50519758;AKOS006307653;AB63117

Chemical Property of 5-Nitronicotinaldehyde

Chemical Property:

• PSA: 75.78000
• LogP: 1.32550
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 152.02219199
• Heavy Atom Count: 11
• Complexity: 166

Purity/Quality:

98%min ^*data from raw suppliers

5-Nitronicotinaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC=C1[N+](=O)[O-])C=O

Technology Process of 5-Nitronicotinaldehyde

There total 5 articles about 5-Nitronicotinaldehyde 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: 71.0%

(5-Nitro-pyridin-3-yl)-methanol (131747-58-5) → 5-nitronicotinaldehyde (87883-20-3)

Guidance literature:

With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.38.2446

Reference yield:

3-Acetoxymethylpyridine-N-oxide (114951-34-7) → 5-nitronicotinaldehyde (87883-20-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) p-nitrobenzoyl chloride, 2) AgNO₃ / 1) CHCl₃, -7 to -5 deg C, 2) -10 to 55 deg C

2: 30 percent / PCl₃ / CHCl₃ / Ambient temperature

3: 60 percent

4: 71 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H₃PO₄ / 1.5 h / Ambient temperature

With phosphoric acid; 4-nitro-benzoyl chloride; silver nitrate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; phosphorus trichloride; In chloroform;

DOI:10.1248/cpb.38.2446

Reference yield:

3-Acetoxymethyl-5-nitropyridine-N-oxide (131748-13-5) → 5-nitronicotinaldehyde (87883-20-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 30 percent / PCl₃ / CHCl₃ / Ambient temperature

2: 60 percent

3: 71 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H₃PO₄ / 1.5 h / Ambient temperature

With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; phosphorus trichloride; In chloroform;

DOI:10.1248/cpb.38.2446

upstream raw materials:

3-aminoacrylaldehyde

nitromalonic aldehyde sodium salt

(5-Nitro-pyridin-3-yl)-methanol

3-Acetoxymethylpyridine-N-oxide

Downstream raw materials:

2,6-dimethyl-4-(5-nitro-3-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester

Refernces

• 1、 Hoffman, Jacob M.,Phillips, Brian T.,Cochran, David W.. "Synthesis of 3-Nitro-5-acylpyridines by Condensation of Sodium Nitromalonaldehyde/Tosyl Chloride with 2-Amino-1-acyl Olefins. Evidence for the Intermediacy of 3-Chloro-2-nitroacrolein". . p. 193 - 195. Retrieved 2007/10/02.