289686-74-4

Basic information

• Product Name: 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE
• Synonyms: 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE
• CAS NO: 289686-74-4
• Molecular Formula: C₉H₁₀ClNO₂
• Molecular Weight: 199.63
• Mol File: 289686-74-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 334°C at 760 mmHg
• Flash Point: 155.8°C
• Appearance: /
• Density: 1.224g/cm³
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE(289686-74-4)
• EPA Substance Registry System: 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE(289686-74-4)

Safety Data

• Hazardous Substances Data: 289686-74-4(Hazardous Substances Data)

Usage

Description

2-Chloro-N-methoxy-N-methylbenzamide is an organic compound with the molecular formula C8H8ClNO2. It is a derivative of benzamide, featuring a chlorine atom at the 2nd position, a methoxy group, and a methyl group attached to the nitrogen atom. 2-CHLORO-N-METHOXY-N-METHYLBENZAMIDE is known for its potential applications in the synthesis of various chemical compounds and pharmaceuticals.

Uses

Used in Chemical Synthesis:
2-Chloro-N-methoxy-N-methylbenzamide is used as a reagent in the synthesis of functionalized β-oxonitriles. These β-oxonitriles are important intermediates in the preparation of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-N-methoxy-N-methylbenzamide is used in the synthesis of potent thiosemicarbazone-based cathepsin L inhibitors. Cathepsin L is a cysteine protease enzyme that plays a crucial role in various biological processes, including tumor progression and metastasis. Inhibitors of this enzyme have potential therapeutic applications in cancer treatment, as they can help regulate the activity of cathepsin L and prevent uncontrolled cell growth.

InChI:InChI=1/C9H10ClNO2/c1-11(13-2)9(12)7-5-3-4-6-8(7)10/h3-6H,1-2H3

Upstream product

• 65-85-0 benzoic acid 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 98-88-4 benzoyl chloride 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 201230-82-2 carbon monoxide 
• 615-41-8 2-iodochlorobenzene 
• 118-91-2 ortho-chlorobenzoic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 609-65-4 o-chlorobenzoyl chloride 

Downstream Products

• 216076-11-8 1-(2-chlorophenyl)-2-(pyridin-4-yl)ethanone 
• 91131-19-0 3-(dimethylamino)-1-(2-chlorophenyl)propan-1-one 
• 1385033-51-1 3-(2-chlorobenzoyl)benzonitrile 
• 24123-67-9 2,2‐dichloro‐1‐(2‐chlorophenyl)ethan‐1‐one 
• 34356-83-7 2,2‐dibromo‐1‐(2‐chlorophenyl)ethan‐1‐one 
• 42330-59-6 (2-chloropyrid-3-yl)methanol 
• 3400-31-5 2-chloro-N-methylbenzamide 
• 348168-03-6 chloroisovalerophenone 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 79478-26-5 2-chloro-2-(2-chlorophenyl)-2-phenylacetaldehyde 
• 653-13-4 1-(2-chlorophenyl)-2,2-difluoroethanone 
• 89-98-5 2-chloro-benzaldehyde 
• 40018-25-5 2-Chlorobenzoyl acetonitrile 

Relevant articles and documents

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

Copper-catalyzed synthesis of weinreb amides by oxidative amidation of alcohols

A simple and efficient protocol has been developed for the oxidative amidation of alcohols to Weinreb amides using tert-butyl hydroperoxide as an oxidant and an inexpensive and air stable copper catalyst. The present protocol is advantageous as it uses commercially affordable alcohols as starting materials. The developed protocol also tolerates various substituted alcohols as starting materials to provide good to excellent yields of the desired products.