Methyl 2,6-dichloro-4-cyanobenzoate

Base Information

• Chemical Name: Methyl 2,6-dichloro-4-cyanobenzoate
• CAS No.: 409127-32-8
• Molecular Formula: C9H5Cl2NO2
• Molecular Weight: 230.05
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00694882
• Wikidata: Q72490007
• Mol file: 409127-32-8.mol

Synonyms:METHYL 2,6-DICHLORO-4-CYANOBENZOATE;409127-32-8;Benzoic acid, 2,6-dichloro-4-cyano-, methyl ester;2,6-dichloro-4-cyanobenzoic acid methylester;Methyl2,6-dichloro-4-cyanobenzoate;2,6-dichloro-4-cyanoBenzoic acid methyl ester;SCHEMBL1707633;DTXSID00694882;SFGSLCVSCBZCIC-UHFFFAOYSA-N;Methyl 4-cyano-2,6-dichlorobenzoate;MFCD13194678;AKOS016009124;AM83007;DS-4321;CS-0150877;FT-0710196;F52287;A873198

Chemical Property of Methyl 2,6-dichloro-4-cyanobenzoate

Chemical Property:

• Boiling Point: 319.6±42.0 °C(Predicted)
• PSA: 50.09000
• Density: 1.45
• LogP: 2.65168
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 228.9697338
• Heavy Atom Count: 14
• Complexity: 261

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,6-dichloro-4-cyanobenzoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=C(C=C1Cl)C#N)Cl

Technology Process of Methyl 2,6-dichloro-4-cyanobenzoate

There total 6 articles about Methyl 2,6-dichloro-4-cyanobenzoate 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: 88.0%

methyl 4-carbamoyl-2,6-dichlorobenzoate (409127-31-7) → methyl 2,6-dichloro-4-cyanobenzoate (409127-32-8)

Guidance literature:

With pyridine; trifluoroacetic anhydride; at 0 - 20 ℃; for 1h;

Reference yield:

dimethyl aminoterephthalate (5372-81-6) → methyl 2,6-dichloro-4-cyanobenzoate (409127-32-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrachloromethane; N-chloro-succinimide / 16 h / 80 °C

2.1: isopentyl nitrite / tetrahydrofuran / 3 h / 20 °C / Reflux

3.1: water; sodium hydroxide / tetrahydrofuran / 48 h / 20 °C

4.1: triethylamine / tetrahydrofuran / 0.33 h / 20 °C

4.2: 18 h / 20 °C

5.1: pyridine; trifluoroacetic anhydride / 1,4-dioxane / 24 h / 20 °C

With pyridine; tetrachloromethane; N-chloro-succinimide; water; triethylamine; trifluoroacetic anhydride; sodium hydroxide; isopentyl nitrite; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm400266t

Reference yield:

2-amino-3,5-dichloro-4-(carbomethoxy)benzoic acid methyl ester (1258298-04-2) → methyl 2,6-dichloro-4-cyanobenzoate (409127-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: isopentyl nitrite / tetrahydrofuran / 3 h / 20 °C / Reflux

2.1: water; sodium hydroxide / tetrahydrofuran / 48 h / 20 °C

3.1: triethylamine / tetrahydrofuran / 0.33 h / 20 °C

3.2: 18 h / 20 °C

4.1: pyridine; trifluoroacetic anhydride / 1,4-dioxane / 24 h / 20 °C

With pyridine; water; triethylamine; trifluoroacetic anhydride; sodium hydroxide; isopentyl nitrite; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1021/jm400266t

upstream raw materials:

methyl 4-carbamoyl-2,6-dichlorobenzoate

dimethyl aminoterephthalate

2-amino-3,5-dichloro-4-(carbomethoxy)benzoic acid methyl ester

dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate

Downstream raw materials:

2,6-dichloro-4-cyanobenzoic acid

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-(4H-1,2,4-triazol-3-yl)benzamide

2,6-dichloro-N₁-(2-(cyclopropanecarboxamido)pyridin-4-yl)terephthalamide

2,6-dichloro-4-cyano-N-(2-(cyclopropanecarboxamido)-pyridin-4-yl)benzamide

Refernces

• 1、 Liang, Jun,Van Abbema, Anne,Balazs, Mercedesz,Barrett, Kathy,Berezhkovsky, Leo,Blair, Wade,Chang, Christine,Delarosa, Donnie,Devoss, Jason,Driscoll, Jim,Eigenbrot, Charles,Ghilardi, Nico,Gibbons, Paul,Halladay, Jason,Johnson, Adam,Kohli, Pawan Bir,Lai, Yingjie,Liu, Yanzhou,Lyssikatos, Joseph,Mantik, Priscilla,Menghrajani, Kapil,Murray, Jeremy,Peng, Ivan,Sambrone, Amy,Shia, Steven,Shin, Young,Smith, Jan,Sohn, Sue,Tsui, Vickie,Ultsch, Mark,Wu, Lawren C.,Xiao, Yisong,Yang, Wenqian,Young, Judy,Zhang, Birong,Zhu, Bing-Yan,Magnuson, Steven. "Lead optimization of a 4-aminopyridine benzamide scaffold to identify potent, selective, and orally bioavailable TYK2 inhibitors". supporting information. p. 4521 - 4536. Retrieved 2013/07/25.
• 2、 -. "JANUS KINASE INHIBITOR COMPOUNDS AND METHODS". Page/Page column 101. . Retrieved 2010/12/29.