1-chloro-2-iodo-4-nitro-benzene

Base Information

• Chemical Name: 1-chloro-2-iodo-4-nitro-benzene
• CAS No.: 74534-15-9
• Molecular Formula: C6H3ClINO2
• Molecular Weight: 283.453
• Hs Code.: 2904909090
• Mol file: 74534-15-9.mol

Synonyms:1-Chloro-2-iodo-4-nitrobenzene;4-Chloro-3-iodonitrobenzene;NSC 223078;1-chloro-2-iodo-4-nitrobenzene;

Chemical Property of 1-chloro-2-iodo-4-nitro-benzene

Chemical Property:

• Melting Point: 78 °C
• Boiling Point: 315.7 °C at 760 mmHg
• Flash Point: 144.7 °C
• PSA: 45.82000
• Density: 2.094 g/cm³
• LogP: 3.37600
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99.3% ^*data from raw suppliers

1-Chloro-2-iodo-4-nitrobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Chloro-2-iodo-4-nitrobenzene is an intermediate for Vismodegib (V674700) and Vismodegib-d4 (V674702), pharmaceuticals that target the hedgehog (Hh) pathway.

Technology Process of 1-chloro-2-iodo-4-nitro-benzene

There total 7 articles about 1-chloro-2-iodo-4-nitro-benzene 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: 99.0%

4-chlorobenzonitrile (100-00-5) → 1-chloro-2-iodo-4-nitrobenzene (74534-15-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; at 20 ℃; for 24h; Cooling with ice;

DOI:10.1016/j.ejmech.2017.09.002

Reference yield: 73.0%

H2NC6H3(Cl)NO2 (6283-25-6) → 1-chloro-2-iodo-4-nitrobenzene (74534-15-9)

Guidance literature:

H₂NC₆H₃(Cl)NO₂; With sulfuric acid; sodium nitrite; In water; at 0 ℃;

With potassium iodide; In water; at 15 ℃;

Reference yield: 28.0%

2-chloro-5-nitrobenzoic acid (2516-96-3) → 1-chloro-2-iodo-4-nitrobenzene (74534-15-9)

Guidance literature:

With oxygen; copper diacetate; silver sulfate; sodium iodide; In dimethyl sulfoxide; at 160 ℃; for 30h; under 760.051 Torr; Schlenk technique;

DOI:10.1039/c8ob01095a

upstream raw materials:

H₂NC₆H₃(Cl)NO₂

2-iodo-4-nitrophenylamine

4-chlorobenzonitrile

2-iodochlorobenzene

Downstream raw materials:

2-(2-chloro-5-nitrophenyl)-pyridine

1-chloro-2-(2-fluoro-phenylethynyl)-4-nitro-benzene

2-chloro-N-(4-chloro-3-iodophenyl)-4-methylsulfonylbenzamide

2-chloro-N-[4-chloro-3-(5-hydroxy-2-pyridyl)phenyl]-4-methylsulfonylbenzamide

Refernces

• 1、 Wang, Fangying,Jiang, Hongxia,Deng, Yufang,Yu, Jiang,Zhan, Miao,Zhao, Lifeng,Chen, Yuanwei. "Design, synthesis and biological evaluation of deuterated Vismodegib for improving pharmacokinetic properties". supporting information. p. 2399 - 2402. Retrieved 2018/06/25.
• 2、 Lu, Wenfeng,Liu, Yongqiang,Ma, Haikuo,Zheng, Jiyue,Tian, Sheng,Sun, Zhijian,Luo, Lusong,Li, Jiajun,Zhang, Hongjian,Yang, Zeng-Jie,Zhang, Xiaohu. "Design, Synthesis, and Structure-Activity Relationship of Tetrahydropyrido[4,3-d]pyrimidine Derivatives as Potent Smoothened Antagonists with in Vivo Activity". . p. 1980 - 1994. Retrieved 2017/09/25.