1418153-02-2

Basic information

• Product Name: phenyl 2,6-dichloronicotinate
• Synonyms: phenyl 2,6-dichloronicotinate
• CAS NO: 1418153-02-2
• Molecular Weight: 268.099
• Mol File: 1418153-02-2.mol

Chemical Properties

• CAS DataBase Reference: phenyl 2,6-dichloronicotinate(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,6-dichloronicotinate(1418153-02-2)
• EPA Substance Registry System: phenyl 2,6-dichloronicotinate(1418153-02-2)

Safety Data

• Hazardous Substances Data: 1418153-02-2(Hazardous Substances Data)

Upstream product

• 38496-18-3 2,6-dichloropyridine-3-carboxylic acid 
• 58584-83-1 2,6-dichloronicotinoyl chloride 
• 108-95-2 phenol 

Downstream Products

• 1418153-27-1 phenyl 2-Chloro-6-(4-methylpiperazin-1-yl)nicotinate 

Relevant articles and documents

Effects of the pyridine 3-substituent on regioselectivity in the nucleophilic aromatic substitution reaction of 3-substituted 2,6-dichloropyridines with 1-methylpiperazine studied by a chemical design strategy

A chemical design strategy has been used to select 3-substituted 2,6-dichloropyridines for the nucleophilic aromatic substitution reaction with 1-methylpiperazine. The aim was to study the dependency of the regioselectivity in these reactions on the character of the pyridine 3-substituent expressed by their lipophilicity (PI), size (MR), and inductive effect (Ip). Interestingly, the regioselectivity did not correlate with any of these parameters, but in a statistically significant manner with the Verloop steric parameter B1, as indicated by the p value of 0.006 (R2 = 0.45). This implies that bulky 3-substituents close to the pyridine ring induce regioselectivity towards the 6-position. Useful in practical synthesis is the different regioselectivity obtained with a carboxylic acid 3-substituent and precursors or derivatives thereof. Thus, in acetonitrile as solvent, 3-carboxylate and 3-amide substituents were preferred to obtain the 2-isomer (9:1 ratio of the 6-isomer), whereas the 3-cyano and 3-trifluoromethyl substitutents were preferred to obtain the 6-isomer (9:1 ratio of the 2-isomer). Analysis of the regioselectivity Rsel for the pyridine 2-position in the reaction of 2,6-dichloro-3-(methoxycarbonyl)pyridine with 1-methylpiperazine in 21 different solvents showed that Rsel could be predicted by the Kamlet-Taft equation: Rsel = 1.28990 + 0.03992α - 0.59417β - 0.46169π* (R2 = 0.95, p = 1.9 × 10-10). Rsel is thus mainly correlated with the ability of the solvent to function as a hydrogen-bond acceptor, as expressed by the solvatochromic β parameter. Thus, the 16:1 regioselectivity for the 2-isomer in DCM (β = 0.10) could be switched to a 2:1 selectivity for the 6-isomer in DMSO (β = 0.76). Copyright