151414-47-0

Basic information

• Product Name: Benzenamine, 2,6-difluoro-4-methoxy- (9CI)
• Synonyms: Benzenamine, 2,6-difluoro-4-methoxy- (9CI);4-Amino-3,5-difluoroanisole;4-Amino-3,5-difluoroanisole, 2,6-Difluoro-p-anisidine;4-AMino-3,5-difluoroanisole[2,6-Difluoro-4-Methoxyaniline];2,6-Difluoro-4-methoxybenzenamine
• CAS NO: 151414-47-0
• Molecular Formula: C₇H₇F₂NO
• Molecular Weight: 159.1333864
• Product Categories: HALIDE
• Mol File: 151414-47-0.mol

Chemical Properties

• Melting Point: 38-40℃
• Boiling Point: 172.4°Cat760mmHg
• Flash Point: 58°C
• Appearance: /
• Density: 1.281g/cm³
• Vapor Pressure: 1.34mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.41±0.10(Predicted)
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: Benzenamine, 2,6-difluoro-4-methoxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 2,6-difluoro-4-methoxy- (9CI)(151414-47-0)
• EPA Substance Registry System: Benzenamine, 2,6-difluoro-4-methoxy- (9CI)(151414-47-0)

Safety Data

• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 151414-47-0(Hazardous Substances Data)

Usage

Uses

2,6-Difluoro-4-methoxyaniline is used as primary and secondary intermediate.

InChI:InChI=1/C7H7F2NO/c1-11-4-2-5(8)7(10)6(9)3-4/h2-3H,10H2,1H3

Upstream product

• 315-14-0 1,3,5-trifluoro-2-nitrobenzene 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 93343-10-3 3,5-difluoroanisol 
• 2713-34-0 3,5-difluorophenol 
• 125369-56-4 2,6-difluoro-4-methoxybenzoyl chloride 
• 372-38-3 1,3,5-trifluorobenzene 
• 123843-65-2 2,6-difluoro-4-methoxybenzoic acid 
• 66684-62-6 1,3-difluoro-5-methoxy-2-nitrobenzene 

Downstream Products

• 1242015-79-7 4-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-N-(2,4,6-trifluorophenyl)-1H-pyrazol-5 amine 
• 1617522-72-1 N-(2,6-difluoro-4-methoxy-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide 
• 1193511-89-5 N-[(6-chloro-3-pyridinyl)methylene]-2,6-difluoro-4-methoxybenzenamine 
• 1146788-84-2 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine 
• 1193354-45-8 2-chloro-5-[1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine 
• 1242015-72-0 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluoro-4-methoxyphenyl)-1,3-dimethyl-1H-pyrazol-5-amine 
• 151414-42-5 2,6-difluoro-4-hydroxyacetanilide 
• 1638490-70-6 1-(2,6-difluoro-4-methoxyphenyl)-4-phenylquinolin-2(1H)-one 
• 1638490-44-4 N-(2,6-difluoro-4-methoxyphenyl)propionamide 

Relevant articles and documents

HYDANTOIN AND THIOHYDANTOIN DERIVATIVES AS ANTIVIRAL DRUGS

The present invention relates to a compound of the following formula (I), or a salt, solvate, tautomer, enantiomer, diastereoisomer or racemic mixture thereof: as well as its use as a drug, notably in the treatment of hepatitis C, its preparation process, and the pharmaceutical compositions containing such a compound.

A convenient synthesis of 4-alkoxy- and 4-hydroxy-2,6-difluoroanilines

Two independent synthetic pathways for the preparation of 4-methoxy, 4-benzyloxy and 4-hydroxy-2,6-difluoroanilines, versatile building blocks in medicinal chemistry, based on diazonium coupling or Curtius-type rearrangements are presented.

MONOCYCLIC AROYLPYRIDINONES AS ANTIINFLAMMATORY AGENTS

The present invention relates to monocyclic aroylpyridinones, processes for their preparation, and their use in medicaments, especially for the treatment of COPD: (formula I).

The Effect of Fluorine Substitution on the Metabolism and Antimalarial Activity of Amodiaquine

Amodiaquine (AQ) (2) is a 4-aminoquinoline antimalarial which causes adverse side effects such as agranulocytosis and liver damage.The observed drug toxicity is believed to be related to the formation of an electrophilic metabolite, amodiaquine imine (AQQI), which can bind to cellular macro-molecules and initiate hypersensitivity reactions. 5'-Fluoroamodiaquine (5'-FAQ, 3), 5',6'-difluoroamodiaquine (5',6'-DIFAQ, 4), 2',6'-difluoroamodiaquine (2',6'-DIFAQ, 5), 2',5',6'-trifluoroamodiaquine (2',5',6'-TRIFAQ, 6) and 4'-dehydroxy-4'-fluoroamodiaquine (4'-deOH-4'-FAQ, 7) have been synthesized to assess the effect of fluorine substitution on the oxidation potential, metabolism, and in vitro antimalarial activity of amodiaquine.The oxidation potentials were measured by cyclic voltammetry, and it was observed that substitution at the 2',6'- and 4'-positions (2',6'-DIFAQ and 4'-deOH'4'-FAQ) produced analogues with significantly higher oxidation potentials than the parent drug.Fluorine substitution at the 2',6'-positions and 4'-position also produced analogues that were more resistant to bioactivation.Thus 2',6'-DIFAQ and 4'-deOH-4'-FAQ produced thioether conjugates corresponding to 2.17percent (SD: +/-0.27percent) and 0percent of the dose compared with 11.87percent (SD: +/-1.31percent) of the dose for amodiaquine.In general the fluorinated analogues had similar in vitro antimalarial activity to amodiaquine against the chloroquine resistant K1 strain of Plasmodium falciparum and the chloroquine sensitive T9-96 strain of P. falciparum with the notable exception of 2',5',6'-TRIFAQ (6).The data presented indicate that fluorine substitution at the 2',6'-positions and replacement of the 4'-hydroxyl of amodiaquine with fluorine produces analogues ( 5 and 7) that maintain antimalarial efficacy in vitro and are more resistant to oxidation and hence less likely to form toxic quinone imine metabolites.

The effect of fluorine substitution on the physicochemical properties and the analgesic activity of paracetamol

The physicochemical properties and analgesic action of six fluorinated analogues of 4-hydroxyacetanilide (paracetamol) have been investigated. Fluorine substitution adjacent to the hydroxyl group increased lipophilicity and oxidation potential whilst substitution adjacent to the amide had little effect on lipophilicity but led to a greater increase in oxidation potential. Lack of coplanarity and conjugation of the amide group and aromatic ring was also apparent with the analogues that had fluorine in the 2 and 6 positions. Introduction of fluorine into the amide group of paracetamol increased the lipophilicity 4-fold and also increased the oxidation potential of paracetamol. ED50 values for analgesic activity in the phenylquinone-induced abdominal constriction test on male Swiss White mice showed that ring substitution by fluorine reduced activity, especially at the 2,6-positions. Introduction of fluorine into the amide group enhanced activity significantly. Correlation of the analgesic activity with the physicochemical properties indicated that conjugation (and planarity) of the amide group with the aromatic ring is essential for activity and that ease of oxidation may also be an important factor.