13421-00-6

Basic information

• Product Name: 5-Chloro-2-iodobenzoic acid
• Synonyms: 5-CHLORO-2-IODOBENZOIC ACID;BUTTPARK 100\07-48;2-Iodo-5-chlorobenzoic acid;5-Chloro-2-iodobnezoic Acid;Benzoic acid, 5-chloro-2-iodo-
• CAS NO: 13421-00-6
• Molecular Formula: C₇H₄ClIO₂
• Molecular Weight: 282.46293
• Product Categories: Benzoic acid;Acids & Esters;Chlorine Compounds;Iodine Compounds
• Mol File: 13421-00-6.mol

Chemical Properties

• Melting Point: 172-174°C
• Boiling Point: 336.352 °C at 760 mmHg
• Flash Point: 157.22 °C
• Appearance: /
• Density: 2.077 g/cm³
• Vapor Pressure: 4.42E-05mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.49±0.10(Predicted)
• CAS DataBase Reference: 5-Chloro-2-iodobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-2-iodobenzoic acid(13421-00-6)
• EPA Substance Registry System: 5-Chloro-2-iodobenzoic acid(13421-00-6)

Safety Data

• Statements: 36/37/38-41
• Safety Statements: 26-36/37/39-39-28
• Hazardous Substances Data: 13421-00-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Chloro-2-iodobenzoic acid is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with specific therapeutic effects.
Used in Agrochemical Production:
In the agrochemical industry, 5-Chloro-2-iodobenzoic acid is utilized as a building block in the creation of compounds that can be used in the development of pesticides and other agricultural chemicals to protect crops and enhance yield.
Used in Organic Synthesis:
5-Chloro-2-iodobenzoic acid is employed as a versatile intermediate in organic synthesis, allowing for the construction of complex organic molecules with diverse applications in various industries.
Used in Drug Discovery:
Due to its potential biological and medicinal properties, such as anti-proliferative and anti-inflammatory effects, 5-Chloro-2-iodobenzoic acid is used in drug discovery research to explore its potential as a therapeutic agent or as a precursor to other bioactive compounds.
Used in Chemical Research:
5-Chloro-2-iodobenzoic acid is of interest to researchers in the field of chemical synthesis, where it can be used to study reaction mechanisms, develop new synthetic routes, and understand the effects of halogen substitution on molecular properties and reactivity.

InChI:InChI=1/C7H4ClIO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)

Upstream product

• 23399-70-4 4-chloro-1-iodo-2-methylbenzene 
• 683238-56-4 2-ethyl-4-chloro-1-iodo-benzene 
• 635-21-2 5-chloroanthranilic acid 
• 7697-37-2 nitric acid 
• 30273-39-3 2-Ethyl-4-chloroaniline 
• 535-80-8 3-chlorobenzoate 

Downstream Products

• 54435-13-1 5-chloro-2-(4-fluorophenylthio)benzoic acid 
• 82341-38-6 5-Chloro-2-(4-ethoxycarbonyl-phenoxy)-benzoic acid 
• 91527-95-6 5-chloro-2-(4-isopropylphenylthio)benzoic acid 
• 74801-51-7 ethyl 3-<2-(2-carboxy-4-chlorophenylthio)phenyl>propionate 
• 82386-90-1 5-chloro-2-iodobenzyl alcohol 
• 90500-14-4 5-chloro-2-iodosobenzoic acid 
• 81890-74-6 2-(2-aminophenylthio)-5-chlorobenzoic acid 
• 93288-98-3 5-chloro-2-(2-methylphenylthio)benzoic acid 
• 54435-12-0 5-Chloro-2-(3-fluoro-phenylsulfanyl)-benzoic acid 
• 13421-01-7 5-chloro-2-(phenylsulfanyl)benzoic acid 
• 5101-53-1 5-Chloro-2-(4-chloro-phenylsulfanyl)-benzoic acid 
• 63186-29-8 5-chloro-2-(4-methoxyphenylthio)benzoic acid 
• 171256-81-8 5-chloro-2-iodobenzoyl chloride 
• 289039-82-3 methyl 5-chloro-2-iodo-benzoate 

Relevant articles and documents

One-Pot Synthesis and Conformational Analysis of Six-Membered Cyclic Iodonium Salts

Two one-pot procedures for the construction of carbon-bridged diaryliodonium triflates and tetrafluoroborates are described. Strong Br?nsted acids enable the effective Friedel-Crafts alkylation with diversely substituted o-iodobenzyl alcohol derivatives, providing diphenylmethane scaffolds, which are subsequently oxidized and cyclized to the corresponding dibenzo[b,e]iodininium salts. Based on NMR investigations and density functional theory (DFT) calculations, we could verify the so-far-undescribed existence of two stable isomers in cyclic iodonium salts substituted with aliphatic side chains in the carbon bridge.

IrIII-Catalyzed Selective ortho-Monoiodination of Benzoic Acids with Unbiased C?H Bonds

An iridium-catalyzed selective ortho-monoiodination of benzoic acids with two equivalent C?H bonds is presented. A wide range of electron-rich and electron-poor substrates undergo the reaction under mild conditions, with >20:1 mono/di selectivity. Importantly, the C?H iodination occurs selectively ortho to the carboxylic acid moiety in substrates bearing competing coordinating directing groups. The reaction is performed at room temperature and no inert atmosphere or exclusion of moisture is required. Mechanistic investigations revealed a substrate-dependent reversible C?H activation/protodemetalation step, a substrate-dependent turnover-limiting step, and the crucial role of the AgI additive in the deactivation of the iodination product towards further reaction.

Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation

A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.

2-Iodo-N-isopropyl-5-methoxybenzamide as a highly reactive and environmentally benign catalyst for alcohol oxidation

Several N-isopropyliodobenzamides were evaluated as catalysts for the oxidation of benzhydrol to benzophenone in the presence of Oxone (2KHSO5·KHSO4·K2SO4) as a co-oxidant at room temperature. A study on the substituent effect of the benzene ring of N-isopropyl-2-iodobenzamide on the oxidation revealed that its reactivity increased in the following order of substitution: 5-NO2 2Me, 3-OMe 5-OAc 5-Cl H, 4-OMe 5-Me 5-OMe. The oxidation of various benzylic and aliphatic alcohols using a catalytic amount of the most reactive 5-methoxy derivative successfully resulted in moderate to excellent yields of the corresponding carbonyl compounds. The high reactivity of the 5-methoxy derivative at room temperature is a result of the rapid generation of the pentavalent species from the trivalent species during the reaction. 5-Methoxy-2-iodobenzamide would be an efficient and environmentally benign catalyst for the oxidation of alcohols, especially benzylic alcohols.

Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds

The sulfuration reaction of 2-(2-iodobenzoyl) substituted, or 2-(2-iodobenzyl) substituted 1,2,3,4-tetrahydroisoquinolines with potassium sulfide proceeded in the presence of copper catalysts to give tetrahydroisoquinoline-fused 1,3-benzothiazine scaffolds in moderate to appropriate yields. This protocol provided an efficient and simple strategy to construct the corresponding benzothiazine derivatives via formation of C(sp3)-S bond and C(sp2)-S bond, which the C-S bonds formed via different routes in this reaction (traditional cross-coupling reaction via the cleavage of C-I bond and oxidative cross-coupling reaction via C(sp3)-H bond functionalization).

Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate

A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.

Lewis Acid Catalyzed Formal Intramolecular [3 + 3] Cross-Cycloaddition of Cyclopropane 1,1-Diesters for Construction of Benzobicyclo[2.2.2]octane Skeletons

A novel Lewis acid catalyzed formal intramolecular [3 + 3] cross-cycloaddition (IMCC) of cyclopropane 1,1-diesters has been successfully developed. This supplies an efficient and conceptually new strategy for construction of bridged bicyclo[2.2.2]octane skeletons. This [3 + 3]IMCC could be run up to gram scale and from easily prepared starting materials. This [3 + 3]IMCC, together with our previously reported [3 + 2]IMCC strategy, can afford either the bicyclo[2.2.2]octane or bicyclo[3.2.1]octane skeletons from the similar starting materials by regulating the substituents on vinyl group.

Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines

Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.

PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: A complementary method to directed ortho lithiation

(Chemical Equation Presented) When the counterion counts: The yield and selectivity of the title transformation of benzoic acid derivatives were improved greatly by using tetraalkyl ammonium salts as additives (see scheme; monoselectivity: 5:1-18:1). These effects are attributed to the influence of counter cations. The halogenated products are versatile intermediates for the construction of substituted aromatic compounds. DMF=N,N-dimethylformamide.