67669-19-6

Basic information

• Product Name: N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE
• Synonyms: N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE;2',4'-DICHLORO-5'-HYDROXYACETANILIDE;2,4-DICHLORO-5-HYDROXYACETANILIDE;5-ACETYLAMINO-2,4-DICHLOROPHENOL
• CAS NO: 67669-19-6
• Molecular Formula: C₈H₇Cl₂NO₂
• Molecular Weight: 220.05
• EINECS: 429-110-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 67669-19-6.mol

Chemical Properties

• Melting Point: 233-236 °C
• Boiling Point: 394.5 °C at 760 mmHg
• Flash Point: 192.4 °C
• Appearance: White to tan powder, crystals or crystalline powder and/or chunks
• Density: 1.519 g/cm³
• Vapor Pressure: 8.67E-07mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE(67669-19-6)
• EPA Substance Registry System: N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE(67669-19-6)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-36-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 67669-19-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,4-Dichloro-5-hydroxyphenyl)acetamide is used as an intermediate in the synthesis of various pharmaceuticals due to its unique chemical structure and potential therapeutic properties.
Used in Agrochemical Industry:
N-(2,4-DICHLORO-5-HYDROXYPHENYL)ACETAMIDE also serves as an intermediate in the development of agrochemicals, contributing to the creation of products that can enhance crop protection and management.
Used as Anti-inflammatory Agent:
N-(2,4-Dichloro-5-hydroxyphenyl)acetamide is being studied for its potential use as an anti-inflammatory agent, given its observed effects in reducing inflammation in animal models.
Used as Analgesic Agent:
Additionally, it has shown promise as an analgesic agent, indicating its potential to alleviate pain, with further research required to confirm its efficacy and safety in humans.
Note: The uses listed are based on the information provided and the compound's potential applications. As research is ongoing, the actual uses may expand or become more defined as more data becomes available.

InChI:InChI=1/C8H7Cl2NO2/c1-4(12)11-7-3-8(13)6(10)2-5(7)9/h2-3,13H,1H3,(H,11,12)

Upstream product

• 7782-50-5 chlorine 
• 64-19-7 acetic acid 
• 621-42-1 meta-hydroxyacetanilide 
• 631-61-8 ammonium acetate 
• 591-27-5 m-Hydroxyaniline 
• 108-24-7 acetic anhydride 

Downstream Products

• 39807-17-5 2,4-dichloro-5-(2-propynyloxy)aniline 
• 189573-21-5 (2,4-dichloro-5-hydroxy)phenylhydrazine hydrochloride 
• 68049-71-8 2-(2,4-dichloro-5-hydroxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-A]pyridin-3(2H)-one 
• 68049-83-2 azafenidin 
• 380843-75-4 bosutinib 
• 380844-49-5 7-(3-chloropropoxy)-4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-3-quinolinecarbonitrile 
• 846023-24-3 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide 
• 65182-98-1 N-(2,4-dichloro-5-methoxybenzene)acetamide 
• 65948-71-2 N-[2,4-dichloro-5-(propan-2-yloxy)phenyl]acetamide 
• 39489-79-7 4,6-dichloro-1-hydroxy-3-aminobenzene 
• 98446-49-2 2,4-dichloro-5-methoxyaniline 
• 50375-04-7 1,3-dichloro-4,6-dimethoxybenzene 
• 380844-03-1 2,4-dichloro-5-propoxyaniline 
• 380844-01-9 2,4-dichloro-5-ethoxyaniline 

Relevant articles and documents

Preparation method of mecitinib raw material (by machine translation)

The method comprises the following steps: preparing,methyl 3 -(-ethyl-)-amido phenol, dichloro - 5 5-methoxyaniline (by reaction with potassium chloride) sodium 2,4 - to generate (dichloro - 5 5-methan)-methaneth, 2,4 -amidobenzylether (in a chlorine substitution reaction). 2,4 - The method comprises the following steps: reacting m-methyl-methanethinonylphenol and hydrogen peroxide, to generate, dichloro - 5 5-methoxyaniline. The method comprises the following steps of reacting m-aminophenol as a raw material to synthesize methyl chloride 2,4 - potassium, and benzoyl (and reacting; with chloromethane in, a mixture) of, sodium, chloride and methyl chloride, and reacting with chloromethane in a reaction condition. (by machine translation)

A PROCESS FOR THE PREPARATION OF BOSUTINIB

The present invention provides an improved process for the preparation of bosutinib and its intermediate 2-cyano-N-(2, 4-dichloro-5-methoxyphenyl)acetamide.

A method for synthesizing intermediate oxadiazon

The invention discloses a method for synthesizing intermediate oxadiazon, comprises the following steps: takes amino phenol as an initial raw material; to m-aminophenol acylation reaction is carried out, thereby obtaining a reaction solution A; the reaction solution A to proceed chlorination reaction, to obtain 2, 4 - dichloro - 5 hydroxy acetanilide; to the 2, 4 - dichloro - 5 hydroxy acetanilide etherification reaction, to obtain 2, 4 - dichloro - 5 isopropoxy acetanilide; to the 2, 4 - dichloro - 5 isopropoxy acetyl aniline to deprotected, get 2, 4 - dichloro - 5 isopropoxyaniline. The invention of 2, 4 - dichloro - 5 - isopropoxy aniline synthesis method to avoid the pollution of the environment, but there are few process steps, high yield.

New Synthetic Process for Bosutinib

A new and improved synthetic route to bosutinib is described on a hectogram scale. The key step is the intramolecular cyclization of a 3-(2-aminophenyl)-3-oxopropanenitrile with N,N-dimethylformamide dimethyl acetal to form the 3-cyano-4-hydroxyquinoline ring of 7-(3-chloropropoxy)-6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile. A practical synthetic method to 2,4-dichloro-5-methoxyaniline is also established. Bosutinib is obtained in 18.0% yield over nine steps from acetovanillone with 98.9% purity (HPLC).

Discovery and development of a commercial synthesis of azafenidin

A commercial synthesis of the DuPont herbicide azafenidin is described. Discovery of a novel synthesis of the triazolinone ring system and a practical, environmentally benign process to 5-cyanovaleramide were critical breakthroughs in enabling azafenidin to be manufactured at an acceptable cost. The process began with the selective hydrolysis of DuPont's nylon intermediate, adiponitrile, to 5-cyanovaleramide. This was converted via Hofmann rearrangement and Pinner-type cyclization to afford the key amidine carboxylate intermediate containing both carbon atoms of the triazolinone ring. The preservation of all six carbon atoms of adiponitrile set up a 2 + 3 cyclocondensation with arylhydrazines, which replaced a costly 4 + 1 cyclocondensation of an amidrazone with phosgene or a phosgene surrogate used in the original route. This new triazolinone process was optimized to afford the commercial product in a highly efficient and economical fashion.

Method of producing 2,4-dichloro-5-hydroxyacetanilide

The present invention relates to a process for preparing 2,4-dichloro-5-hydroxyacetanilide by reacting 3-hydroxyacetanilide with sulfuryl chloride in the presence of from 3 to 30 parts by weight of an aliphatic carboxylic acid having from 1 to 6 carbon atoms per part by weight of 3-hydroxyacetanilide with vigorous mixing at from 20 to 100° , removing gaseous components from the reaction mixture, setting a ratio of from 1.0 to 6 parts by weight of aliphatic carboxylic acid per part by weight of 3-hydroxyacetanilide employed and removing 2,4-dichloro-5-hydroxyacetanilide as a solid.