15990-43-9

Basic information

• Product Name: N-Benzylniacin
• Synonyms: 1-Benzyl-3-carboxypyridinium hydroxide inner salt;1-benzyl pyridinium-3-carboxylate;N-BENZYLNIACIN;N-BENZYLNICOTINAMIDE;N-Benzyl nicotinate betaine;N-Benzylpyridinium-3-carboxylate;pyridinium,3-carboxy-1-(phenylmethyl)-,hydroxide,innersalt;Pyridinium,3-carboxy-1-(phenylmethyl)-,innersalt
• CAS NO: 15990-43-9
• Molecular Formula: C₁₃H₁₁NO₂
• Molecular Weight: 213.23
• EINECS: 240-129-1
• Mol File: 15990-43-9.mol

Chemical Properties

• Appearance: light yellow paste
• Density: 1.09 g/cm³
• CAS DataBase Reference: N-Benzylniacin(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzylniacin(15990-43-9)
• EPA Substance Registry System: N-Benzylniacin(15990-43-9)

Safety Data

• Hazardous Substances Data: 15990-43-9(Hazardous Substances Data)

Usage

Chemical Properties

N-Benzylniacin(BPC) is a colorless to yellowish transparent liquid.

Uses

N-Benzylniacin can be used as a top brightener and leveling agent in alkaline zinc plating.

Synthetic route

1-benzylnicotinamide chloride (5096-13-9) → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
With sodium hydroxide
Multi-step reaction with 2 steps 1: 80 percent / benzene / 2 h / Ambient temperature 2: 0.48 g / water / Ambient temperature View Scheme

1'-Benzyl-3,4,5,6,1',2'-hexahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid amide (75340-31-7) → N-benzyl nicotinic acid (15990-43-9) + Bis-(1-benzyl-3-carbamoyl-1,4-dihydro-pyridyl)-ether (75340-29-3)

Conditions	Yield
With water Ambient temperature;	A 0.48 g B 0.12 g

1-benzyl-3-carbomethoxy pyridinium iodide → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
With Dowex 1 (OH(-) form) X8 Yield given;

nicotinic acid (59-67-6) → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4 / 24 h / Heating 2: benzene / 3 h / Heating 3: Dowex 1 (OH(-) form) X8 View Scheme

methyl 3-pyridinecarboxylate (93-60-7) → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene / 3 h / Heating 2: Dowex 1 (OH(-) form) X8 View Scheme

nicotinamide (98-92-0) → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: 80 percent / benzene / 2 h / Ambient temperature 3: 0.48 g / water / Ambient temperature View Scheme

benzyl chloride (100-44-7) → N-benzyl nicotinic acid (15990-43-9)

Conditions	Yield
Multi-step reaction with 3 steps 2: 80 percent / benzene / 2 h / Ambient temperature 3: 0.48 g / water / Ambient temperature View Scheme

Upstream product

• 75340-31-7 1'-Benzyl-3,4,5,6,1',2'-hexahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid amide 
• 100-44-7 benzyl chloride 
• 98-92-0 nicotinamide 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 59-67-6 nicotinic acid 
• 5096-13-9 1-benzylnicotinamide chloride 

Relevant articles and documents

INDUCTION OF CELL ARREST IN G2: STRUCTURAL SPECIFICITY OF TRIGONELLINE

Synthetic analogues of N-methyl nicotinic acid, trigonelline, were prepared to test the structural features necessary for the induction of cellular arrest in G2 in Pisum sativum.Analogues that (1) were regioisomers of trigonelline, (2) possessed different 1,3-substituents, ad (3) contained additional substituents on the pyridine ring were tested for their ability to induce cell arrest in G2 and to anatogize trigonelline induced arrest in G2.Only N-methyl-3-quinoline-carboxic acid and 1-methyl nicotinamide induced cell arrest in G2, and 1-methyl-4-pyridine carboxylic acid and 1-methyl-2-pyridine carboxylic acid were effective trigonelline antagonists.These data further support a specific role for trigonelline in the induction of cell arrest in G2.Key words: Pisum sativum; Leguminosae; pea; trigonelline; structural specificity; structural analogues; cell arrest; G2.

COVALENT ADDUCTS FROM 1,3-DISUBSTITUTED PYRIDINIUM SALTS AND PIPERIDINE

Covalent adducts 3a-f have been isolated from the reaction between piperidine and pyridinium salts 1a-f. 3a-f are stable both in the solid state and in apolar solvents, whereas their fast dissociation back to piperidine and pyridinium ions occurs in aqueous solution.The latter, in the alkaline environment produced by the amine, yields the correspondent pseudobases, which are key intermediates of the subsequent reactions.For instance, the pseudobases from 1a,b can undergo either a ring-opening reaction or a redox process with the corresponding pyridinium cations.