5-iodopyridine-2-carboxylic Acid

Base Information

• Chemical Name: 5-iodopyridine-2-carboxylic Acid
• CAS No.: 32046-43-8
• Molecular Formula: C₆H₄INO₂
• Molecular Weight: 249.008
• Hs Code.: 2933399090
• European Community (EC) Number: 852-188-6
• DSSTox Substance ID: DTXSID70430971
• Nikkaji Number: J1.331.468C
• Wikidata: Q82244730
• Mol file: 32046-43-8.mol

Synonyms:5-Iodopicolinic acid;32046-43-8;5-iodopyridine-2-carboxylic Acid;2-Pyridinecarboxylic acid, 5-iodo-;5-Yodopicolinate;SCHEMBL3630126;DTXSID70430971;MFCD09910324;AKOS016007556;CS-W022397;SB21207;DS-11019;FT-0647060;EN300-67213;O11456;A875725;Z1069125846

Chemical Property of 5-iodopyridine-2-carboxylic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 188-190 °C
• Refractive Index: 1.677
• Boiling Point: 355.22oC at 760 mmHg
• PKA: 3.46±0.10(Predicted)
• Flash Point: 168.631oC
• PSA: 50.19000
• Density: 2.124g/cm3
• LogP: 1.38440
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 248.92868
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

98%min ^*data from raw suppliers

5-IodopicolinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1I)C(=O)O
• Uses: 5-Iodopicolinic Acid is used to prepare bis(5-iodopicolinato)oxovanadium(IV) as an antidiabetic agent. The zinc(II) complex with 5-Iodopicolinic Acid also shows insulinomimetic activity.

Technology Process of 5-iodopyridine-2-carboxylic Acid

There total 9 articles about 5-iodopyridine-2-carboxylic 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:

5-amino-2-cyanopyridine (55338-73-3) → 5-Iodpicolinsaeure (32046-43-8) + 2-cyano-5-iodopyridine (41960-47-8)

Guidance literature:

With toluene-4-sulfonic acid; potassium iodide; sodium nitrite; In water; acetonitrile; at 5 - 20 ℃; for 4.16667h;

Reference yield:

2-bromo-5-nitropyridine (4487-59-6) → 5-Iodpicolinsaeure (32046-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) 6M aq. HCl / 1.) DMSO, 180 deg C, 5 min, 2.) reflux, 90 min

2: 86 percent / 25percent aq. NH₃, H₂S / 125 - 135 °C

3: 1.) aq. NaNO₂, HCl, 2.) urea, 3.) 10percent aq. KI

With hydrogenchloride; ammonium hydroxide; hydrogen sulfide; urea; potassium iodide; sodium nitrite;

DOI:10.1002/jlcr.2580361005

Reference yield:

5-nitro-pyridin-2-ylamine (4214-76-0,67476-67-9) → 5-Iodpicolinsaeure (32046-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) 48 percent HBr, Br₂; 2.) NaNO₂ / 1) 30-40 deg C; 2) -5 deg C, H₂O; 10-15 Deg C, 90 min.; 3) 40 deg C_. 15 min

2: dimethylsulfoxide / 0.08 h / 180 °C

3: 54 percent / HCl / 1.5 h / Heating

4: 70 percent / H₂S, 25 percent NH₃

5: 1) conc. HCl, NaNO₂, urea; 2) KI / 1) H₂O, -5 to 0 deg C, 10 min, 0 deg C, 15 min; 2) H₂O, 0 deg C, 5 min

With hydrogenchloride; ammonium hydroxide; hydrogen sulfide; hydrogen bromide; bromine; urea; potassium iodide; sodium nitrite; In dimethyl sulfoxide;

upstream raw materials:

3-iodo-6-methylpyridine

5-amino-pyridine-2-carboxylic acid

2-bromo-5-nitropyridine

5-nitropicolinic acid

Refernces

• 1、 Beer,Haerberli,Ametamey,Schubiger. "Comparison of two synthetic methods to obtain [18F] N-(2-aminoethyl)-5-fluoropyridine-2-carboxamide, a potential MAO-B imaging tracer for PET". . p. 933 - 945. Retrieved 2007/10/02.