3-Chloro-2-iodobenzoic acid

Base Information

• Chemical Name: 3-Chloro-2-iodobenzoic acid
• CAS No.: 123278-03-5
• Molecular Formula: C7H4ClIO2
• Molecular Weight: 282.465
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID40560936
• Nikkaji Number: J1.880.332A
• Wikidata: Q82444587
• Mol file: 123278-03-5.mol

Synonyms:3-chloro-2-iodobenzoic acid;123278-03-5;3-CHLORO-2-IODO-BENZOIC ACID;BENZOIC ACID, 3-CHLORO-2-IODO-;MFCD06808824;3-Chloro-2-iodobenzoicacid;SCHEMBL1222476;DTXSID40560936;IHSNWQTZBUIFSL-UHFFFAOYSA-N;BCP20542;AKOS015909206;AB30453;DS-17033;SY102784;CS-0041180;A805039

Chemical Property of 3-Chloro-2-iodobenzoic acid

Chemical Property:

• Boiling Point: 360.5 °C at 760 mmHg
• Flash Point: 171.8 °C
• PSA: 37.30000
• Density: 2.077 g/cm³
• LogP: 2.64280
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 281.89445
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

98%min ^*data from raw suppliers

3-Chloro-2-iodobenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)Cl)I)C(=O)O

Technology Process of 3-Chloro-2-iodobenzoic acid

There total 6 articles about 3-Chloro-2-iodobenzoic acid 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: 58.0%

3-chlorobenzoate (535-80-8) → 5-chloro-2-iodo-benzoic acid (13421-00-6) + 3-chloro-2-iodo-benzoic acid (123278-03-5)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; iodine; silver(I) acetate; triethylamine; at 23 ℃; for 18h; regioselective reaction; Sealed tube;

DOI:10.1002/chem.202002204

Reference yield: 55.0%

3-chlorobenzoate (535-80-8) → 3-chloro-2-iodo-benzoic acid (123278-03-5)

Guidance literature:

3-chlorobenzoate; With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; In tetrahydrofuran; at -50 ℃; for 4h;

With iodine; In tetrahydrofuran; at -50 - 20 ℃; Further stages.;

DOI:10.1021/jo026514t

Reference yield:

2-amino-3-chlorobenzoic acid (6388-47-2) → 3-chloro-2-iodo-benzoic acid (123278-03-5)

Guidance literature:

2-amino-3-chlorobenzoic acid; With hydrogenchloride; sodium nitrite; In water; at 0 - 5 ℃; for 0.5h; Inert atmosphere;

With sulfuric acid; potassium iodide; In water; at 10 - 90 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c3ra42474j

upstream raw materials:

2-iodo-3-nitrobenzoic acid

3-amino-2-iodo-benzoic acid

3-chlorobenzoate

3-acetylamino-2-iodo-benzoic acid

Downstream raw materials:

3-chloro-2-iodobenzoyl chloride

3-chloro-2-iodobenzaldehyde

Refernces

• 1、 Boelke, Andreas,Nachtsheim, Boris J.. "Evolution of N-Heterocycle-Substituted Iodoarenes (NHIAs) to Efficient Organocatalysts in Iodine(I/III)-Mediated Oxidative Transformations". supporting information. p. 184 - 191. Retrieved 2019/12/11.
• 2、 Weis, Erik,Johansson, Magnus J.,Martín-Matute, Belén. "IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds". supporting information. p. 10185 - 10190. Retrieved 2020/07/31.