2-Iodopyridine
- Product Name
- 2-Iodopyridine
- CAS No.
- 5029-67-4
- Chemical Name
- 2-Iodopyridine
- Synonyms
- JACS-5029-67-4;2-lodopyridine;2-IODOPYRIDINE;2-Pyridyl iodide;Pyridine, 2-iodo-;2-Iodine Pyridine;2-Iodopyridine 98%;2-Iodopyridine 2-IODOPYRIDINE, 95+%;2-Iodopyridine≥ 98% (GC)
- CBNumber
- CB2754297
- Molecular Formula
- C5H4IN
- Formula Weight
- 205
- MOL File
- 5029-67-4.mol
2-Iodopyridine Property
- Melting point:
- 118-120℃
- Boiling point:
- 52 °C (lit.)
- Density
- 1.928 g/mL at 25 °C (lit.)
- refractive index
- n20/D 1.6320(lit.)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- Solid
- pka
- pK1:1.82(＋1) (25°C)
- color
- Pale yellow
- Water Solubility
- Slightly soluble in water.
- Sensitive
- Light Sensitive
- InChI
- InChI=1S/C5H4IN/c6-5-3-1-2-4-7-5/h1-4H
- InChIKey
- CCZWSTFVHJPCEM-UHFFFAOYSA-N
- SMILES
- C1(I)=NC=CC=C1
- CAS DataBase Reference
- 5029-67-4(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 558761
- Product name
- 2-Iodopyridine
- Purity
- 98%
- Packaging
- 5g
- Price
- $347
- Updated
- 2025/07/31
- Product number
- 558761
- Product name
- 2-Iodopyridine
- Purity
- 98%
- Packaging
- 1g
- Price
- $76.9
- Updated
- 2023/06/20
- Product number
- I0533
- Product name
- 2-Iodopyridine (stabilized with Na2S2O3)
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $65
- Updated
- 2025/07/31
- Product number
- I0533
- Product name
- 2-Iodopyridine (stabilized with Na2S2O3)
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $259
- Updated
- 2025/07/31
- Product number
- I719400
- Product name
- 2-Iodopyridine
- Packaging
- 5g
- Price
- $75
- Updated
- 2021/12/16
2-Iodopyridine Chemical Properties,Usage,Production
Chemical Properties
Light yellow liquid
Uses
2-Iodopyridine can be synthesized from 2-chloropyridine or 2-bromopyridine via treatment with iodotrimethylsilane.
2-Iodopyridine is a halogenated building block. It is a reagent used in the preparation of human NAD+-dependent 15-hydroxyprostaglandin dehydrogenase inhibitors.
Uses
2-Iodopyridine is a reagent used in the preparation of human NAD+-dependent 15-hydroxyprostaglandin dehydrogenase inhibitors.
Reactions
2-Iodopyridine and 3-alkoxy-2-iodopyridines are oxidized by DMDO to give PyIO2 , which serve as oxidants for alcohols and sulfides.
In palladium-catalyzed aminocarbonylation of 2-iodopyridine, 3-iodopyridine and iodopyrazine were coupled with CO and various primary and secondary amines. The biologically relevant N-substituted nicotinamides and 3-pyridyl-glyoxylamides were obtained from 3-iodopyridine as a result of simple and double carbon monoxide insertions, respectively. The chemoselectivity towards the ketoamide can be increased by the elevation of CO pressure. On the other hand, N-alkyl and N-aryl-carboxamides were obtained exclusively from CO pressure of 1 to 90 bar by using 2-iodopyridine and iodopyrazine.
Pd-catalyzed aminocarbonylation of 2-iodopyridine and 3-iodopyridine with primary and secondary amines.
Synthesis Reference(s)
Tetrahedron Letters, 31, p. 6757, 1990 DOI: 10.1016/S0040-4039(00)97163-6
General Description
2-Iodopyridine can be synthesized from 2-chloropyridine or 2-bromopyridine via treatment with iodotrimethylsilane.
Synthesis
109-04-6
5029-67-4
General procedure for the synthesis of 2-iodopyridine from 2-bromopyridine: the aromatic Finkelstein reaction is used. Since copper(I) iodide is sensitive to moisture and oxygen, the reaction needs to be carried out under argon protection using the standard Schlenk technique. In a two-necked pear-shaped flask equipped with a reflux condenser, (het) aryl bromine feedstock, NaI (using 2 equivalents per bromine exchange) and CuI (using 5 mol% per bromine exchange) were added. N,N'-dimethylethylenediamine (L1) or N,N'-dimethyl-1,2-cyclohexanediamine (L2) (10 mol% per bromine exchange used) and anhydrous 1,4-dioxane (0.5 mL per 1 mmol of NaI used) were subsequently added. The resulting suspension was heated to 110 °C and maintained for 18 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into a 25% aqueous NH3 solution. The blue solution was diluted to twice the original volume with H2O and extracted three times with CH2Cl2. For the case of 2,2'-bipyridine, the combined organic phases were additionally washed with aqueous EDTA; otherwise, the combined organic phases were simply washed with brine and dried with MgSO4. The solvent is removed by distillation under reduced pressure to give pure 2-iodopyridine. If necessary, the crude product can be further purified by column chromatography or recrystallization.
References
[1] Tetrahedron Letters, 1999, vol. 40, # 23, p. 4339 - 4342
[2] Tetrahedron, 2000, vol. 56, # 10, p. 1349 - 1360
[3] Synthesis (Germany), 2014, vol. 46, # 8, p. 1085 - 1090
[4] Phosphorus and Sulfur and the Related Elements, 1984, vol. 21, p. 197 - 204
[5] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
2-Iodopyridine Preparation Products And Raw materials
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View Lastest Price from 2-Iodopyridine manufacturers
- Product
- 2-Iodopyridine 5029-67-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-12
- Product
- 2-Iodopyridine 5029-67-4
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.00%
- Supply Ability
- 100 Tons min
- Release date
- 2021-09-01
- Product
- 2-Iodopyridine 5029-67-4
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10