2-Chloro-N-methoxy-N-methylbenzamide

Base Information

• Chemical Name: 2-Chloro-N-methoxy-N-methylbenzamide
• CAS No.: 289686-74-4
• Molecular Formula: C9H10ClNO2
• Molecular Weight: 199.637
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30592660
• Nikkaji Number: J3.455.481A
• Wikidata: Q82486877
• Mol file: 289686-74-4.mol

Synonyms:2-Chloro-N-methoxy-N-methylbenzamide;289686-74-4;Benzamide, 2-chloro-N-methoxy-N-methyl-;SCHEMBL308205;DTXSID30592660;ZBRUSXSYQDZHQM-UHFFFAOYSA-N;AB8889;MFCD02684306;AKOS008952916;2-Chloro-N-methoxy-N-methyl-benzamide;AM90085;AC-16373;BS-22188;DA-26357;SY038730;A849025;F1903-0129

Chemical Property of 2-Chloro-N-methoxy-N-methylbenzamide

Chemical Property:

• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.541
• Boiling Point: 334°C at 760 mmHg
• Flash Point: 155.8°C
• PSA: 29.54000
• Density: 1.224g/cm³
• LogP: 1.97340
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99%min ^*data from raw suppliers

2-Chloro-N-methoxy-N-methylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C(=O)C1=CC=CC=C1Cl)OC
• Uses: 2-Chloro-N-methoxy-N-methylbenzamide was used as a reagent in the synthesis of functionalized β-oxonitriles. Also used in the synthesis of potent thiosemicarbazone based cathepsin L inhibitors.

Technology Process of 2-Chloro-N-methoxy-N-methylbenzamide

There total 8 articles about 2-Chloro-N-methoxy-N-methylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + o-chlorobenzoyl chloride (609-65-4) → 2‐chloro‐N‐methoxy‐N‐methylbenzamide (289686-74-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 20.1667h;

Reference yield: 93.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + ortho-chlorobenzoic acid (118-91-2) → 2‐chloro‐N‐methoxy‐N‐methylbenzamide (289686-74-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2012.05.059

Reference yield: 90.0%

carbon monoxide (201230-82-2) + 2-iodochlorobenzene (615-41-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2‐chloro‐N‐methoxy‐N‐methylbenzamide (289686-74-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; sodium carbonate; In acetonitrile; at 80 ℃; for 8h; under 760.051 Torr; Autoclave; Inert atmosphere;

DOI:10.1039/c4ob00729h

upstream raw materials:

N,O-dimethylhydroxylamine*hydrochloride

o-chlorobenzoyl chloride

N,0-dimethylhydroxylamine

ortho-chlorobenzoic acid

Downstream raw materials:

(3-bromophenyl)-(2-chlorophenyl)methanone

3-(dimethylamino)-1-(2-chlorophenyl)propan-1-one

3-(2-chlorobenzoyl)benzonitrile

(2-chloropyrid-3-yl)methanol

Refernces

• 1、 Gim, Hyo Jin,Jung, Michael E.. "Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines". supporting information. p. 2548 - 2552. Retrieved 2019/06/08.
• 2、 Das, Riki,Kapur, Manmohan. "Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides". . p. 1114 - 1126. Retrieved 2018/06/18.