Methyl 5-fluoro-2-iodobenzoate

Base Information

• Chemical Name: Methyl 5-fluoro-2-iodobenzoate
• CAS No.: 1202897-48-0
• Molecular Formula: C₈H₆FIO₂
• Molecular Weight: 280.037
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID90704863
• Wikidata: Q82637446
• Mol file: 1202897-48-0.mol

Synonyms:methyl 5-fluoro-2-iodobenzoate;1202897-48-0;5-fluoro-2-iodobenzoic acid methyl ester;MFCD12965043;Methyl5-fluoro-2-iodobenzoate;methyl 3-fluoro-6-iodobenzoate;SCHEMBL1151008;DTXSID90704863;BRUNIDAHRLZQOH-UHFFFAOYSA-N;TD1035;AKOS016004770;BP-20284;DS-14185;SY114214;5-Fluoro-2-iodo-benzoic acid methyl ester;CS-0032319;FT-0749413;EN300-7370889;A892262

Chemical Property of Methyl 5-fluoro-2-iodobenzoate

Chemical Property:

• Boiling Point: 264.4±25.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.823±0.06 g/cm3(Predicted)
• LogP: 2.21690
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 279.93966
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

Methyl5-Fluoro-2-iodobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)F)I
• Uses: methyl 5-fluoro-2-iodobenzoate (is a useful reactant in the synthesis of arene-?fused cyclic β-?ketoesters via an homoconjugate addition and decarboxylative Dieckmann cyclization.

Technology Process of Methyl 5-fluoro-2-iodobenzoate

There total 2 articles about Methyl 5-fluoro-2-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: 98.0%

methanol (67-56-1) + 5-fluoro-2-iodobenzoic acid (52548-63-7) → methyl 3-fluoro-6-iodobenzoate (1202897-48-0)

Guidance literature:

With sulfuric acid; for 6h; Reflux;

Reference yield:

2-amino-5-fluoro-benzoic acid methyl ester (319-24-4) → methyl 3-fluoro-6-iodobenzoate (1202897-48-0)

Guidance literature:

2-amino-5-fluoro-benzoic acid methyl ester; With toluene-4-sulfonic acid; In acetonitrile; Inert atmosphere;

With 4-bromo-1-(2,2-difluorovinyl)-2-iodobenzene; sodium nitrite; In water; acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.8b02128

Reference yield: 95.0%

diethyl cyclopropane-1,1-dicarboxylate (1559-02-0) + methyl 3-fluoro-6-iodobenzoate (1202897-48-0) → diethyl 2-(4-fluoro-2-(methoxycarbonyl)phenethyl)malonate

Guidance literature:

methyl 3-fluoro-6-iodobenzoate; With TurboGrignard; In tetrahydrofuran; 2-methyltetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere; Sealed tube;

diethyl cyclopropane-1,1-dicarboxylate; With 1,3-dimethyl-2-imidazolidinone; copper(I) iodide dimethyl sulfide complex; In tetrahydrofuran; 2-methyltetrahydrofuran; at -78 - 23 ℃; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.8b00754

upstream raw materials:

methanol

5-fluoro-2-iodobenzoic acid

2-amino-5-fluoro-benzoic acid methyl ester

Downstream raw materials:

5-fluoro-2-iodobenzaldehyde

methyl 4-fluoro-[1,1'-biphenyl]-2-carboxylate

Refernces

• 1、 -. "CHEMICAL COMPOUNDS". Paragraph 0294; 0295. . Retrieved 2014/12/09.
• 2、 -. "DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS". Page/Page column 50-51. . Retrieved 2012/11/07.