626-02-8 Usage
Description
3-Iodophenol is an organic compound that features a phenol group with an iodine atom attached at the 3rd position. It is a versatile chemical intermediate with a wide range of applications in various industries due to its unique chemical properties.
Uses
Used in Organic Synthesis:
3-Iodophenol is used as a chemical intermediate for esterification, which allows for the formation of esters that can be used in various applications, such as pharmaceuticals, agrochemicals, and fragrances.
Used in Electrophilic Aromatic Substitution:
3-Iodophenol is used as a substrate in electrophilic aromatic substitution reactions, which are essential for the synthesis of various organic compounds, including dyes, plastics, and pharmaceuticals.
Used in Alkylation:
3-Iodophenol is used as a reactant in alkylation reactions, which involve the introduction of an alkyl group to the phenol molecule. This process is crucial for the production of various organic compounds, such as alkylphenols and their derivatives.
Used in Nucleophilic Aromatic Substitution:
3-Iodophenol is used as a substrate in nucleophilic aromatic substitution reactions, which are important for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.
Used in Mitsunobu Reactions:
3-Iodophenol is used as a reactant in Mitsunobu reactions, which are a class of organic reactions that involve the conversion of alcohols to their corresponding esters or ethers. This process is useful for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Transition Metal-Catalyzed Cross-Coupling:
3-Iodophenol is used as a reactant in transition metal-catalyzed cross-coupling reactions, which are essential for the formation of carbon-carbon bonds in various organic compounds. This process is crucial for the synthesis of complex organic molecules, such as pharmaceuticals, agrochemicals, and advanced materials.
Used in Acylation:
3-Iodophenol is used as a reactant in acylation reactions, which involve the introduction of an acyl group to the phenol molecule. This process is important for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and dyes.
Used in Oxidation Reactions:
3-Iodophenol is used as a substrate in oxidation reactions, which are essential for the synthesis of various organic compounds, including quinones, phenolic acids, and other oxidized derivatives. These compounds have applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.
Synthesis
3-Iodophenol Synthesis:1）Add potassium tert-butoxide (67.3 mg, 0.60 mmol, 2.0 eq.), oxime (74.5 mg, 0.60 mmol, 2.0 eq.), and 4′-bromoacetophenone (59.7 mg, 0.30 mmol, 1.0 eq.) to an oven-dry screw-cap 8mL reaction vial.2）Add anhydrous DMSO (1.5 mL) to the solids a magnetic stir bar.3）Close the vial and sparge the reaction mixture with N2 for 15 minutes, seal with parafilm.4）Stir the reaction mixture and heat at 100°C in a metal heating block for 16 h.5）Dilute the mixture with CH2Cl2 or EtOAc (20 mL), pour into a mixture of water (10mL) and brine (5 mL), acidify with 10% aq HCl (~1 mL).6）Collect the organic phase and extract the aqueous phase with CH2Cl2 or EtOAc (3×20mL).7）Combine the organics, dry (MgSO4) and concentrate under reduced pressure.8）Purify the crude product to give 3-Iodophenol by column chromatography (30% EtOAc in hexane).
Check Digit Verification of cas no
The CAS Registry Mumber 626-02-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 626-02:
(5*6)+(4*2)+(3*6)+(2*0)+(1*2)=58
58 % 10 = 8
So 626-02-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H5IO/c7-5-2-1-3-6(8)4-5/h1-4,8H
626-02-8Relevant articles and documents
Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions
Brittain, William D. G.,Cobb, Steven L.
supporting information, p. 2110 - 2115 (2019/02/27)
Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour.
Method for continuous flow synthesis of phenol-based compound
-
Paragraph 0053; 0054, (2017/07/21)
The present invention provides a method for continuous flow synthesis of a phenol-based compound represented by a formula (III), wherein the method is performed in two static mixers, a tubular reactor and an oil-water separator, wherein the two static mixers, the tubular reactor and the oil-water separator are sequentially connected in series. The method comprises that an acid solution and an aniline compound represented by a formula (I) are pumped into the static mixer A; the mixture of the acid solution and the compound represented by the formula (I) flows out from the static mixer A and flows into the static mixer B connected to the static mixer A; a sodium nitrite solution is pumped into the static mixer B, and a reaction is performed to produce a diazonium salt solution represented by a formula (II); and the solution represented by the formula (II) flows out from the static mixer B, is pumped into the tubular reactor connected to the static mixer B, and then into the oil-water separator connected to the tubular reactor, and the water phase is separated to obtain the compound represented by the formula (III). According to the present invention, the method has characteristics of short reaction time, solvent saving and high yield, and can well solve the problems in the synthesis of the phenol-based compound through diazotization hydrolysis in the intermittent kettle type reactor. The formulas (I), (II) and (III) are defined in the specification.
Continuous-flow hydroxylation of aryl iodides promoted by copper tubing
Cyr, Patrick,Charette, André B.
supporting information, p. 1409 - 1412 (2014/06/23)
A simple and ligand-free synthesis of phenols from the corresponding aryl iodides in a continuous-flow system is described. The reaction is complete in only 4 to 20 minutes when heated between 150 to 165 °C in a reactor consisting of a commercially available copper coil. An example of trapping of the phenoxide in situ is also shown.
