5658-61-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-CHLOROPHENOXY)-2-METHYLPROPANAMIDE is used as an intermediate in the synthesis of pharmaceuticals for its potential anti-inflammatory properties and as a candidate for the treatment of certain types of cancers.
Used in Agricultural Chemical Industry:
2-(4-CHLOROPHENOXY)-2-METHYLPROPANAMIDE is used as an intermediate in the synthesis of agricultural chemicals, contributing to the development of new compounds for pest control and crop protection.

InChI:InChI=1/C10H12ClNO2/c1-10(2,9(12)13)14-8-5-3-7(11)4-6-8/h3-6H,1-2H3,(H2,12,13)

Upstream product

• 5542-60-9 clofibryl chloride 
• 7462-74-0 2-bromo-2-methylpropanamide 
• 106-48-9 4-chloro-phenol 
• 882-09-7 Clofibric acid 
• 1193-00-6 sodium 4-chlorophenolate 

Downstream Products

• 62100-41-8 α-hydroxy-isobutyric acid-(4-chloro-anilide) 
• 124188-20-1 2-(4-chloro-2-nitrophenoxy)-2-methylpropanamide 
• 22786-73-8 2-(4-Chloro-phenoxy)-N-hydroxymethyl-2-methyl-propionamide 
• 69846-08-8 1-nicotinoil-2-(4-clorofenossi)-2-metilpropilammine 
• 88222-07-5 acetil-2-(4-clorofenossi)-2-metilpropilammina 
• 88222-08-6 1-carbamoil-2-(4-clorofenossi)-2-metilpropilammina 
• 124188-37-0 6-chloro-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one 
• 124188-36-9 2-hydroxy-2-methyl-N-(4-chloro-2-nitrophenyl)propionamide 
• 124188-17-6 2-(4-chloro-2-nitrophenoxy)-2-methylpropanoic acid 
• 106-47-8 4-chloro-aniline 

Relevant academic research and scientific papers

Facilitated transport of two model steroids by esters and amides of clofibric acid

A series of novel dermal penetration enhancers, esters and amides of clofibric acid, was synthesized. The permeation parameters and skin retention of two steroids (hydrocortisone-21-acetate and betamethasone-17-valerate) in propylene glycol were studied with athymic nude mouse skin by in vitro diffusion cell techniques in the presence of the novel enhancer compounds. Isopropyl myristate, dimethyl lauramide, and 1-dodecylazacycloheptan-2-one (laurocapram, Azone) were used as control enhancers. The most satisfactory enhancement of both the ester and amide series was observed with clofibric acid octyl amide; coadministration increased skin retention of hydrocortisone acetate after 24 h by 3.5-fold and that of betamethasone valerate by 2.9- fold. Diffusion cell receptor concentrations increased 51.6- and 10.3-fold, respectively, during the same time period. However, the enhancer compound in this case was applied to the skin 1 h prior to each of the steroids. The amide analogues were more effective than the equivalent ester compounds of the same carbon chain length. The best enhancer compounds (2c, 3d, 3e, and 3f) were nonirritating to athymic mouse skin in vivo.

The Conversion of Phenols to Primary and Secondary Aromatic Amines via a Smiles Rearrangement

The conversion of phenols to 2-aryloxy-2-methylpropanamides (1) and the Smiles rearrangement of these to N-aryl-2-hydroxy-2-methyl propanamides are described; hydrolysis of the latter compounds yields anilines.The scope and limitations of reaction are discussed.Routes, some involving α-lactams, from phenols to N-substituted derivatives of (1) have been developed.Under the conditions of the Smiles rearrangement these secondary 2-methylpropanamides can form directly anilides, N-alkylanilines, or benzoxazinones.

ipso Nitration in p-halophenyl ethers

Addition of nitronium ion ipso to halogen occurs on nitration of the p-haloanisoles in acetic anhydride at -60 deg C.In the cases of p-fluoro- and p-chloro-anisole, addition of the nitronium ion is reversible and only small amounts of ipso products are obtained.With p-bromoanisole nitrodebromination occurs.When p-halophenyl ethers containing a trapping substituent, e.g., 2-(4-chlorophenoxy)-2-methylpropanoic acid, are used as substrates, substantial amounts of the spiro diene with nitro ipso to halogen, e.g., 3,3-dimethyl-8-chloro-8-nitro-1,4-dioxaspirodeca-6,9-dien-2-one, can be isolated.The results demonstrate that extensive ipso attack at the halogen-substituted position is general in the nitration of p-halophenyl ethers.Key words: ipso nitration, ether, diene, p-haloanisole.