Structure Application
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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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Methyl 4-iodosalicylate Suppliers

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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

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