540-38-5

Basic information

• Product Name: 4-Iodophenol
• Synonyms: Phenol,p-iodo- (6CI,8CI);1-Iodo-4-hydroxybenzene;4-Hydroxyiodobenzene;4-Hydroxyphenyl iodide;NSC 91464;p-Hydroxyiodobenzene;p-Iodophenol
• CAS NO: 540-38-5
• Molecular Formula: C₆H₅IO
• Molecular Weight: 220.00777
• EINECS: 208-745-5
• Mol File: 540-38-5.mol

Chemical Properties

• Melting Point: 89-94℃
• Boiling Point: 287.2 °C at 760 mmHg
• Flash Point: 112.4 °C
• Appearance: light brown powder
• Density: 2.001 g/cm³
• Vapor Pressure: 0.00146mmHg at 25°C
• Refractive Index: 1.669
• Water Solubility: slightly soluble
• CAS DataBase Reference: 4-Iodophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodophenol(540-38-5)
• EPA Substance Registry System: 4-Iodophenol(540-38-5)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:; R36/37/38:
• Safety Statements: S22:; S26:; S36/37/39:
• Hazardous Substances Data: 540-38-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Iodophenol is used as a precursor in the field of organic synthesis for the production of various other compounds. Its unique structure and reactivity make it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
4-Iodophenol is used as a starting material for the synthesis of certain pharmaceutical compounds. Its iodine atom can be replaced or modified in reactions, allowing for the creation of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
4-Iodophenol is used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in organic reactions enables the development of new and effective products for agricultural use.
Used in Specialty Chemicals:
4-Iodophenol is used as a key component in the production of specialty chemicals, including dyes, fragrances, and other industrial chemicals. Its ability to participate in a wide range of chemical reactions makes it a valuable asset in the synthesis of these diverse products.

InChI:InChI=1/C6H5IO/c7-5-1-3-6(8)4-2-5/h1-4,8H

Upstream product

• 60-29-7 diethyl ether 
• 591-51-5 phenyllithium 
• 108-95-2 phenol 
• 106-41-2 4-bromo-phenol 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 
• 1878-94-0 4-iodophenoxyacetic acid 
• 13997-71-2 1-(allyloxy)-4-iodobenzene 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 123-91-1 1,4-dioxane 
• 7790-99-0 Iodine monochloride 
• 7553-56-2 iodine 
• 7782-68-5 iodic acid 
• 104-91-6 p-nitrosophenol 

Downstream Products

• 599-52-0 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one 
• 90794-36-8 2-(4-iodo-phenoxy)-butyric acid 
• 95306-89-1 1-iodo-4-propyloxybenzene 
• 50686-15-2 (4-nitro-phenyl)-carbamic acid-(4-iodo-phenyl ester) 
• 50686-05-0 (3-nitro-phenyl)-carbamic acid-(4-iodo-phenyl ester) 
• 87-86-5 Pentachlorophenol 
• 2012-29-5 2,4-diiodophenol 
• 21784-73-6 4-iodo-2-nitrophenol 
• 37404-23-2 2-(4-iodophenoxy)-2-methylpropanoic acid 
• 187407-15-4 2,6-dibromo-4-iodophenol 
• 88-89-1 2,4,6-Trinitrophenol 
• 123-31-9 hydroquinone 

Relevant articles and documents

Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C?H Halogenation

A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C?H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur

Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics

Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

Aryl phenol compound as well as synthesis method and application thereof

The invention discloses a synthesis method of an aryl phenol compound shown as a formula (3). All systems are carried out in an air or nitrogen atmosphere, and visible light is utilized to excite a photosensitizer for catalyzation. In a reaction solvent, ArNR1R2 as shown in a formula (1) and water as shown in a formula (2) are used as reaction raw materials and react under the auxiliary action of acid to obtain the aryl phenol compound as shown in a formula (3). The ArNR1R2 in the formula (1) can be primary amine and tertiary amine, can also be steroid and amino acid derivatives, and can also be drugs or derivatives of propofol, paracetamol, ibuprofen, oxaprozin, indomethacin and the like. The synthesis method has the advantages of cheap and easily available raw materials, simple reaction operation, mild reaction conditions, high reaction yield and good compatibility of substrate functional groups. The fluid reaction not only can realize amplification of basic chemicals, but also can realize amplification of fine chemicals, such as synthesis of drugs propofol and paracetamol. The invention has wide application prospect and use value.

Highly recyclable Ti0.97Ni0.03O1.97catalyst coated on cordierite monolith for efficient transformation of arylboronic acids to phenols and reduction of 4-nitrophenol

A stable Ni2+substituted TiO2catalyst (Ti0.97Ni0.03O1.97) has been synthesized by a solution combustion method with an average crystallite size of 7.5 nm. Ti1?xNixO2?x(x= 0.01-0.06) crystallizes in the TiO2anatase structure with Ni2+substituted in Ti4+ion sites and Ni taking a nearly square planar geometry. This catalyst is found to be highly active in the transformation of diverse arylboronic acids to the corresponding phenols. The catalyst coated cordierite monolith can even be recycled for up to 20 cycles with a cumulative TOF of 1.8 × 105h?1. In scale-up reactions, various phenols are synthesized by employing a single cordierite monolith. It also shows high performance in the reduction of 4-nitrophenol.

Catalyst-free rapid conversion of arylboronic acids to phenols under green condition

A catalyst-free and solvent-free method for the oxidative hydroxylation of aryl boronic acids to corresponding phenols with hydrogen peroxide as the oxidizing agent was developed. The reactions could be performed under green condition at room temperature within very short reaction time. 99% yield of phenol could be achieved in only 1 min. A series of different arenes substituted aryl boronic acids were further carried out in the hydroxylation reaction with excellent yield. It was worth nothing that the reaction could completed within 1 min in all cases in the presence of ethanol as co-solvent.

An efficient Ti0.95Cu0.05O1.95 catalyst for ipso – hydroxylation of arylboronic acid and reduction of 4-nitrophenol

A stable, active and selective Ti0.95Cu0.05O1.95 catalyst, crystallized in anatase TiO2 structure with 5% Cu2+ ions substituted for Ti4+ ions with 5% oxide ion vacancy has been synthesized by solution combustion method. The catalyst was coated over a cordierite monolith (Mg2Al4Si5O18) by solution combustion method. By the first principle density functional theory (DFT) calculations, 48 atoms bulk structure has been optimized and density of states (DOS) has been calculated. Ti – O bond distribution in Ti0.95Cu0.05O1.95 has been compared with pure TiO2. Bond distribution analysis has shown longer Cu – O and Ti – O bonds compared to those in CuO and TiO2 creating Cu2+ and oxide ion vacancy as electrophilic and nucleophilic active sites, respectively. This catalyst was found to be very active for ipso – hydroxylation of arylboronic acid and 4-nitrophenol reduction reactions at room temperature. Catalyst coated cordierite monolith was used in the recycling process of the reaction for 20 cycles and cumulative turnover frequency was found to be 184,840 h?1. Ti0.95Cu0.05O1.95 catalyst coated on cordierite monolith enhanced the rate of the reaction compared to powder catalyst and made the handling and recycling of the catalyst very easy. Graphic abstract: [Figure not available: see fulltext.]

Method for preparing alcohol and phenol through aerobic hydroxylation reaction of boric acid derivative in absence of photocatalyst

The invention discloses a method for preparing alcohol and phenol through aerobic hydroxylation reaction of a boric acid derivative in the absence of a photocatalyst, wherein the boric acid derivativeis aryl boronic acid or alkyl boronic acid, and the corresponding target compounds are respectively a phenol-based compound and an alcohol-based compound. According to the method, by using a boric acid derivative as a reaction substrate, an additive is added under a solvent condition, and a hydroxylation reaction is performed under aerobic and illumination conditions to obtain a corresponding target compound. According to the invention, the new strategy is provided for the synthesis of phenols through aerobic hydroxylation of aryl boronic acid without a photocatalyst; the catalyst-free aerobic hydroxylation method for photocatalysis of aryl boronic acid or alkyl boronic acid by using triethylamine as an additive is firstly disclosed; and the new method has advantages of photocatalyst-freecondition, wide substrate range and good functional group compatibility.

Bimetallic photoredox catalysis: Visible light-promoted aerobic hydroxylation of arylboronic acids with a dirhodium(ii) catalyst

We report the use of a rhodium(II) dimer in visible light photoredox catalysis for the aerobic oxidation of arylboronic acids to phenols under mild conditions. Spectroscopic and computational studies indicate that the catalyst Rh2(bpy)2(OAc)4 (1) undergoes metal-metal to ligand charge transfer upon visible light irradiation, which is responsible for catalytic activity. Further reactivity studies demonstrate that 1 is a general photoredox catalyst for diverse oxidation reactions.

Aerobic photooxidative hydroxylation of boronic acids catalyzed by anthraquinone-containing polymeric photosensitizer

We report herein the synthesis of a polymeric photosensitizer and its application in aerobic photooxidative hydroxylation of boronic acids. The polymeric photosensitizer was synthesized by the condensation of anthraquinone-2-carbonyl chloride (AQ-2-COCl) with poly (2-hydroxyethyl methacrylate) (PHEMA). The photo-oxidative hydroxylation of boronic acids using anthraquinone-containing-poly (2-hydroxyethyl methacrylate) (AQ-PHEMA) was then explored and shown to exhibit high efficiency and broad scope. Moreover, AQ-PHEMA could be easily recovered and reused for more than 20 times without significant loss of the catalytic activity.