529-28-2

Basic information

• Product Name: 2-Iodoanisole
• Synonyms: 1-Iodo-2-methoxybenzene, 2-Iodophenyl methyl ether;Adjacent iodine benzene Methyl ether;2-IODOANISOLE;1-IODO-2-METHOXYBENZENE;O-IODOANISOLE;1-iodo-2-methoxy-benzen;Anisole, o-iodo-;Benzene, 1-iodo-2-methoxy-
• CAS NO: 529-28-2
• Molecular Formula: C₇H₇IO
• Molecular Weight: 234.03
• EINECS: 208-456-4
• Product Categories: alkyl Iodine;Aromatic Ethers;Anisole;Anisoles, Alkyloxy Compounds & Phenylacetates;Iodine Compounds;Building Blocks;C2 to C8;Chemical Synthesis;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 529-28-2.mol

Chemical Properties

• Melting Point: 588.5 °C
• Boiling Point: 125-126 °C19 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: Clear yellow/Liquid
• Density: 1.799 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.622(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: alcohol: miscible(lit.)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• Merck: 14,5028
• BRN: 1860243
• CAS DataBase Reference: 2-Iodoanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodoanisole(529-28-2)
• EPA Substance Registry System: 2-Iodoanisole(529-28-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 529-28-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Iodoanisole is used as a key intermediate in the synthesis of various organic compounds. Its application is particularly notable in the palladium/copper-catalyzed synthesis of o-(1-alkynyl)anisoles, which are important for the development of pharmaceuticals and other specialty chemicals.
Used in the Suzuki Reaction:
In the field of organic chemistry, 2-Iodoanisole is utilized as a reactant in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, specifically in the synthesis of biaryl compounds. This reaction is significant in the production of various pharmaceuticals, agrochemicals, and advanced materials.
Used in Enantioselective Synthesis:
2-Iodoanisole is also used as a starting material in the enantioselective Heck arylation, a reaction that allows for the creation of chiral molecules with a single handedness. This is crucial in the pharmaceutical industry, as many drugs exhibit different biological activities depending on their chirality. The use of 2-Iodoanisole in this process aids in the development of more effective and targeted medications.

InChI:InChI=1/C7H7IO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3

Upstream product

• 69180-60-5 2-(iodosyl)anisole 
• 90-04-0 2-methoxy-phenylamine 
• 20469-63-0 1-iodo-2,4-dimethoxybenzene 
• 100-66-3 methoxybenzene 
• 76-03-9 trichloroacetic acid 
• 578-57-4 2-bromoanisole 
• 95765-82-5 C₁₄H₁₄N₂O₃S 
• 5720-06-9 2-Methoxyphenylboronic acid 
• 3425-23-8 2-methoxybenzenediazonium chloride 
• 10034-85-2 hydrogen iodide 
• 118700-33-7 2-dichloroiodanyl-anisole 
• 1250409-81-4 2-methoxyphenyliodonium-(5-[2,2-dimethyl-1,3-dioxane-4,6-dione])ylide 
• 579-75-9 2-Methoxybenzoic acid 
• 38227-87-1 2,2,6,6-tetramethylpiperidinyl-lithium 

Downstream Products

• 6333-10-4 Hydroxy-phenyl-bis-(2-methoxy-phenyl)-methan 
• 861792-35-0 bis-(3-iodo-4-methoxy-phenyl)-methane 
• 14065-23-7 1-methoxy-2-[(4-methoxyphenyl)thio]benzene 
• 4877-93-4 2,2'-Dimethoxybiphenyl 
• 459423-07-5 7-(2-methoxyphenyl)benzo[d][1,3]dioxole-5-carbaldehyde 
• 92-18-2 N,N-diethyl-3-methoxyaniline 
• 100-66-3 methoxybenzene 
• 578-58-5 2-methylmethoxybenzene 
• 579-75-9 2-Methoxybenzoic acid 
• 93321-11-0 1-(2-methoxyphenyl)naphthalene 
• 873377-73-2 (2-methoxy-phenyl)-(3-methoxy-phenyl)-sulfide 
• 126770-56-7 1-methoxy-2-[(2-methoxyphenyl)sulfanyl]benzene 
• 855951-90-5 2-(8-nitro-[1]naphthyl)-anisole 
• 59345-33-4 2-Methoxyphenyl-4’-methylphenylsulfide 

Relevant articles and documents

Lithium cadmate-mediated deprotonative metalation of anisole: Experimental and computational study

Lithium cadmates bearing different ligands were compared with efficient (TMP)3CdLi (TMP = 2,2,6,6-tetramethylpiperidino) for their ability to deprotometalate anisole. The generated arylcadmates were evidenced using I 2. The results show that it is possible to replace only one of the TMP (with a piperidino, a diisopropylamino, a butyl, or a sec-butyl) without important yield drop. In the light of DFT calculations, reaction pathways were proposed for the deprotocadmations of anisole using a triamino, an alkyldiamino, and an aminodialkyl cadmate.

The synthesis of bromo and iodo trifunctionalised tribenzosilatranes

A reliable synthetic route towards selective derivatisation at the 6′,6″ and 6? positions of tribenzosilatranes with bromo or iodo groups has been developed. As these groups can be reacted further, this extends the chemistry associated with tribenzosilatranes. In this report we present a direct synthesis of bromo 8 and iodo 9 trisubstituted tribenzosilatranes. Commercially available o-anisidine 1 was transformed into the triarylamine 3 in a two-step sequence, which was halogenated to furnish the tribromo 4 or the triiodo 5 substituted triamines, respectively. Subsequent deprotection of the methyl ethers furnished the novel tripod ligands 6 and 7. A transilylation reaction in the last step led to the synthesis of the desired para-halogenated tribenzosilatranes 8 and 9.

TMP (2,2,6,6-tetramethylpiperidide)-aluminate bases: Lithium-mediated alumination or lithiation-alkylaluminium-trapping reagents?

The lithium TMP-aluminate bases "LiTMP·Al(iBu) 3" 1 and "LiTMP·Al(TMP)(iBu) 2" 2, where TMP is 2,2,6,6-tetramethylpiperidide, have recently come under the spotlight as "aluminating" reagents in that they can perform aluminium-hydrogen exchange on a wide variety of aromatic substrates. Previous studies have intimated that 1 existed as a single species in THF solution formulated as [(THF)·Li(μ-TMP)(μ-iBu)Al( iBu)2] 1·THF, having a contacted ion pair structure as evidenced by an X-ray crystallographic study of isolated crystals. But here using anisole as a case substrate it is revealed that pre-crystallised 1·THF cannot deprotonate anisole at all whether in hexane or THF solution contradicting earlier in situ applications of 1 which revealed near quantitative metallation of anisole. NMR spectroscopic studies of 1 made in situ in THF solution ascribe this reactivity distinction from 1·THF to complex equilibria involving five major species in LiTMP·THF, Al( iBu)3·THF, [{Li(THF)4} +{Al(TMP)(iBu)3}-] 1·(THF)4, [(THF)·Li(μ-TMP)(μ-OC4H 7)Al(iBu)2], 4, and (TMP)Al( iBu)2·THF. Reagent 2 in contrast is found to exist as only two separated homometallic species in LiTMP·THF and (TMP)Al( iBu)2·THF in THF solution. The constitutions of 1 and 2 in non-polar hexane solution are also revealed. With the aid of DFT calculations, discussion focuses on the fact that none of the aluminate species present in THF solutions of 1 or 2 can deprotonate/metallate anisole, instead the metallation processes appear to be LiTMP lithiations followed immediately by trapping by an alkylaluminium complex, in a metal exchange which drives the reaction to the product (arylaluminated) side. the Partner Organisations 2014.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust

Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.

Decarboxylative Suzuki-Miyaura coupling of (hetero)aromatic carboxylic acids using iodine as the terminal oxidant

A novel methodology for the decarboxylative Suzuki-Miyaura-type coupling has been established. This process uses iodine or a bromine source as both the decarboxylation mediator and the terminal oxidant, thus avoiding the need for stoichiometric amounts of transition metal salts previously required. Our new protocol allows for the construction of valuable biaryl architectures through the coupling of (hetero)aromatic carboxylic acids with arylboronic acids. The scope of this decarboxylative Suzuki reaction has been greatly diversified, allowing for previously inaccessible non-ortho-substituted aromatic acids to undergo this transformation. The procedure also benefits from low catalyst loadings and the absence of stoichiometric transition metal additives.

Mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen: Development of a base-catalyzed iododeboronation for radiolabeling applications

An investigation into the mechanism of Cu-catalyzed aryl boronic acid halodeboronation using electrophilic halogen reagents is reported. Evidence is provided to show that this takes place via a boronate-driven ipso-substitution pathway and that Cu is not required for these processes to operate: General Lewis base catalysis is operational. This in turn allows the rational development of a general, simple, and effective base-catalyzed halodeboronation that is amenable to the preparation of 125I-labeled products for SPECT applications.

Facile and practical synthesis of π-extended oxepins by benzannulation and intramolecular cyclization

π-Extended oxepins 1 and dimer 8 were synthesized by the benzannulation of the corresponding asymmetric diarylacetylene derivatives and 2-(phenylethynyl)benzaldehyde followed by the Cu-catalyzed intramolecular cyclization. The optical properties of the π-extended oxepins 1 and 8 are also investigated.