Methyl 2,6-dichloro-4-iodobenzoate

Base Information

• Chemical Name: Methyl 2,6-dichloro-4-iodobenzoate
• CAS No.: 1098619-73-8
• Molecular Formula: C₈H₅Cl₂IO₂
• Molecular Weight: 330.937
• Mol file: 1098619-73-8.mol

Synonyms:Methyl 2,6-dichloro-4-iodobenzoate;2,6-dichloro-4-iodoBenzoic acid methyl ester;Benzoic acid, 2,6-dichloro-4-iodo-, methyl ester

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

Chemical Property:

• PSA: 26.30000
• Density: 1.909
• LogP: 3.38460
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 9 articles about Methyl 2,6-dichloro-4-iodobenzoate 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: 90.0%

methyl 4-amino-2,6-dichlorobenzoate (232275-49-9) → 2,6-dichloro-4-iodo-benzoic acid methyl ester (1098619-73-8)

Guidance literature:

methyl 4-amino-2,6-dichlorobenzoate; With hydrogenchloride; sodium nitrite; In water; at -5 - 0 ℃;

With potassium iodide; In water; at 0 - 20 ℃;

Reference yield:

1,3-dichloro-2-methyl-5-nitrobenzene (7149-69-1) → 2,6-dichloro-4-iodo-benzoic acid methyl ester (1098619-73-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium permanganate / water; pyridine / 28 h / Reflux

2.1: N,N-dimethyl-formamide; thionyl chloride / 1,2-dichloro-ethane / 2 h / Reflux

2.2: 20 h / 50 °C

3.1: sodium dithionite / water; ethanol / 22.5 h / 25 °C / Reflux

4.1: hydrogenchloride / water / 3 h / 25 °C

4.2: 0.33 h / 0 °C

4.3: 1 h / 25 °C

With hydrogenchloride; potassium permanganate; thionyl chloride; sodium dithionite; N,N-dimethyl-formamide; In pyridine; ethanol; water; 1,2-dichloro-ethane;

DOI:10.1016/j.tet.2015.12.026

Reference yield:

4-tert-butoxycarbonylamino-2,6-dichloro-benzoic acid methyl ester (409127-35-1) → 2,6-dichloro-4-iodo-benzoic acid methyl ester (1098619-73-8)

Guidance literature:

4-tert-butoxycarbonylamino-2,6-dichloro-benzoic acid methyl ester; With hydrogenchloride; In methanol; at 50 ℃; for 3h;

With sulfuric acid; In water;

With copper(l) iodide; potassium iodide; sodium nitrite; more than 3 stages;

upstream raw materials:

methyl 4-amino-2,6-dichlorobenzoate

4-tert-butoxycarbonylamino-2,6-dichloro-benzoic acid methyl ester

(3,5-Dichloro-4-hydroxy-phenyl)-carbamic acid tert-butyl ester

4-amino-2,6-dichlorophenol

Downstream raw materials:

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

Refernces

• 1、 Liang, Jun,Van Abbema, Anne,Balazs, Mercedesz,Barrett, Kathy,Berezhkovsky, Leo,Blair, Wade S.,Chang, Christine,Delarosa, Donnie,DeVoss, Jason,Driscoll, Jim,Eigenbrot, Charles,Goodacre, Simon,Ghilardi, Nico,MacLeod, Calum,Johnson, Adam,Bir Kohli, Pawan,Lai, Yingjie,Lin, Zhonghua,Mantik, Priscilla,Menghrajani, Kapil,Nguyen, Hieu,Peng, Ivan,Sambrone, Amy,Shia, Steven,Smith, Jan,Sohn, Sue,Tsui, Vickie,Ultsch, Mark,Williams, Karen,Wu, Lawren C.,Yang, Wenqian,Zhang, Birong,Magnuson, Steven. "Identification of an imidazopyridine scaffold to generate potent and selective TYK2 inhibitors that demonstrate activity in an in vivo psoriasis model". supporting information. p. 4370 - 4376. Retrieved 2017/09/12.
• 2、 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.