ChemicalBook > CAS DataBase List > Methyl 4-iodosalicylate

Methyl 4-iodosalicylate

Structure Application

Product Name: Methyl 4-iodosalicylate
CAS No.: 18179-39-0
Chemical Name: Methyl 4-iodosalicylate
Synonyms: Methyl4-Iodosilicylate;METHYL 4-IODOSALICYLATE;Methyl4-Iodosalicylate>Methyl 4-iodosalicylate 97%;4-Iodosalicylic Acid Methyl Ester;2-Hydroxy-4-iodobenzoic Acid Methyl Ester;Benzoic acid, 2-hydroxy-4-iodo-, methyl ester;Methyl 4-iodosalicylate, 5-Iodo-2-(methoxycarbonyl)phenol;Methyl 2-Hydroxy-4-iodobenzoate 4-Iodosalicylic Acid Methyl Ester 2-Hydroxy-4-iodobenzoic Acid Methyl Ester
CBNumber: CB6498889
Molecular Formula: C8H7IO3
Formula Weight: 278.04
MOL File: 18179-39-0.mol

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Methyl 4-iodosalicylate Property

Melting point:: 69-73 °C
Boiling point:: 309.7±32.0 °C(Predicted)
Density: 1.880±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
form: powder to crystal
pka: 8.91±0.10(Predicted)
color: White to Gray to Brown
Sensitive: Light Sensitive
InChIKey: WUFUURSWOJROKY-UHFFFAOYSA-N

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Safety

Hazard Codes: T
Risk Statements: 25
Safety Statements: 45
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
F: 8
Hazard Note: Toxic
PackingGroup: III
HS Code: 2918290090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word: Danger
Hazard statements: H301Toxic if swalloed

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 652636
Product name: Methyl 4-iodosalicylate
Purity: 97%
Packaging: 25g
Price: $85.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: 652636
Product name: Methyl 4-iodosalicylate
Purity: 97%
Packaging: 5g
Price: $67.8
Updated: 2023/06/20

TCI Chemical

Product number: M1908
Product name: Methyl 4-Iodosalicylate
Purity: >98.0%(GC)
Packaging: 5g
Price: $105
Updated: 2025/07/31

TCI Chemical

Product number: M1908
Product name: Methyl 4-Iodosalicylate
Purity: >98.0%(GC)
Packaging: 25g
Price: $320
Updated: 2025/07/31

TRC

Product number: M219895
Product name: Methyl2-Hydroxy-4-iodobenzoate
Packaging: 50mg
Price: $45
Updated: 2021/12/16

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Methyl 4-iodosalicylate Chemical Properties,Usage,Production

Structure

2-hydroxy-4-iodobenzoic acid methyl ester (methyl 4-iodosalicylate, C8H7IO3) allows for an effective way of incorporating the methyl salicylates within larger organic molecules, using such methodologies as McClure protocols, which take advantage of the iodine atom at the 4-position of the aromatic ring for the formation of carbon-carbon bonds. The iodine atom is also capable of forming supramolecular synthons, which may be useful for crystal engineering. At 90 K, the methyl 4-iodosalicylat displays monoclinic (P21/c) symmetry with one molecule in the asymmetric unit. Intermolecular hydrogen bonding interactions occur between the hydroxy groups of one molecule and the carbonyl oxygen atom of the methyl ester of an adjacent molecule to form a centrosymmetric dimeric pair with H⋯O = 2.53 (4) Å. An O3—H3⋯O2 intramolecular hydrogen bond also exists with an H⋯O distance of 2.05 (4) Å. The C5⋯C8 [3.326 (3) Å] and O3⋯H1C (2.51 Å) interactions provide only short contacts between the stacks of offset (102) parallel sheets, which make up the crystal. These sheets, in turn, contain the inversion-generated hydrogen-bonded dimers. The non-hydrogen atoms of the molecule are essentially coplanar with no displacement from the mean molecular plane greater than 0.132 Å.

Application

4-Iodosalicylic acid methyl ester is an ester organic compound that can be used as a chemical reagent.

Synthesis

16870-28-3

74-88-4

18179-39-0

General procedure for the synthesis of methyl 4-iodosalicylate from 2-hydroxy-4-iodobenzoic acid and iodomethane: 4-iodosalicylic acid (7.3 g, 27.65 mmol) was dissolved in 41 mL of DMF, NaHCO3 (2.78 g, 33.18 mmol) was added, and CO2 was released during the reaction and the mixture was stirred for 5 min. Iodomethane (2.66 mL, 5.85 g, 41.47 mmol, 1.5 eq.) was then added and the reaction mixture was heated with stirring at 40 °C for 5 h (the reaction progress was monitored by TLC). After completion of the reaction, the mixture was diluted with 170 mL of water and 170 mL of ethyl acetate (EA). The organic layer was washed sequentially with 170 mL of 5% NaHCO3 solution and 170 mL of 5% NaCl solution and dried with Na2SO4. Evaporation of the solvent gave about 9 g of crude product (in the form of a black oil), which was purified by column chromatography: 100 g of silica gel (SiO2) was used as stationary phase, and the eluent was pure hexane, which was subsequently adjusted to a solvent mixture of hexane:ethyl acetate (100:2). Finally, 5.86 g of pure product was obtained in 76.5% yield.

References

[1] Patent: US2016/2269, 2016, A1. Location in patent: Paragraph 0253; 0254

Methyl 4-iodosalicylate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Methyl 4-iodosalicylate manufacturers

Career Henan Chemical Co

Product: METHYL 4-IODOSALICYLATE 18179-39-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2020-01-02

18179-39-0, Methyl 4-iodosalicylateRelated Search:

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18179-39-0

C7H7IO2Si