2142-70-3

Basic information

• Product Name: 2'-Iodoacetophenone
• Synonyms: 2'-IODOACETOPHENONE;2-IODOACETOPHENONE;O-IODOACETOPHENONE;2''-IODOACETOPHENONE 97%;2'-Iodoacetophenone, 98+%;2'-IODOACETOPHENONE, 99+%;1-(2-iodophenyl)ethanone;1-(2-Iodophenyl)ethan-1-one
• CAS NO: 2142-70-3
• Molecular Formula: C₈H₇IO
• Molecular Weight: 246.05
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);Adehydes, Acetals & Ketones;Iodine Compounds;C7 to C8;Carbonyl Compounds;Ketones
• Mol File: 2142-70-3.mol

Chemical Properties

• Boiling Point: 139-140°C 12mm
• Flash Point: 218 °F
• Appearance: Clear yellow/Liquid
• Density: 1.72 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00779mmHg at 25°C
• Refractive Index: n20/D 1.618(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive: Light Sensitive
• BRN: 2325078
• CAS DataBase Reference: 2'-Iodoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Iodoacetophenone(2142-70-3)
• EPA Substance Registry System: 2'-Iodoacetophenone(2142-70-3)

Safety Data

• Hazard Codes: C
• Statements: 36/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2142-70-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2'-Iodoacetophenone is used as a synthetic intermediate for the production of a range of pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 2'-Iodoacetophenone is used as a building block for the synthesis of various organic compounds. Its reactivity and functional groups make it a valuable precursor in the creation of complex molecules.
Used in Synthesis of Indene Derivatives:
2'-Iodoacetophenone is used as a starting material for the synthesis of indene derivatives, which are important compounds in the chemical industry with applications in the production of dyes, pigments, and pharmaceuticals.
Used in Synthesis of Di-(o-acetylphenyl)acetylene:
This halogenated aromatic ketone is also utilized in the synthesis of di-(o-acetylphenyl)acetylene, a compound that finds use in the development of advanced materials and has potential applications in the electronics and materials science industries.
Used in Synthesis of Indenol Derivatives:
Furthermore, 2'-Iodoacetophenone is employed in the synthesis of indenol derivatives, which are valuable intermediates in the production of various organic compounds, including those with potential applications in the fragrance and flavor industries.

Preparation

2'-Iodoacetophenone can be synthesized by diazotization of 2-acetylaniline. To a solution of p-TsOH (22.80 g, 120 mmol) in CH3CN (160 mL) was added an aromatic amine (40 mmol). The resulting amine salt suspension was cooled to 0-5°C. A solution of NaNO2 (5.52 g, 80 mmol) in H2O (12 mL) and KI (16.6 g, 100 mmol) in H2O (12 mL) were added sequentially. The reaction mixture was stirred for 10 minutes, then allowed to warm to ambient temperature and stirred until all the amine was consumed. To the reaction mixture were then added H2O (700 mL), NaHCO3 (1M; until pH=9-10) and Na2S2O3 (2M, 80 mL). The reaction mixture was extracted with EtOAc and purified by column chromatography (hexanes:EtOAc, 9:1 v/v) to give 2'-iodoacetophenone:yellow oil in 94% yield.

Reactions

2'-Iodoacetophenone is a bioactive molecule that reacts with boronic acids to form aryl boronic acid derivatives. This reaction can be carried out in chlorobenzene or dihedral solvents, and it is scalable and applicable to a variety of boronic acids. The product of this reaction is an organocatalyst for the synthesis of bioactive molecules. 2'-Iodoacetophenone also reacts with dipole-containing additives to form dichlorodiphenyldichloroethane, which has been used as a fungicide, insecticide, and herbicide.

InChI:InChI=1/C8H7IO/c1-6(10)7-4-2-3-5-8(7)9/h2-5H,1H3

Upstream product

• 551-93-9 2-aminoacetophenone 
• 615-42-9 1,2-Diiodobenzene 
• 108-24-7 acetic anhydride 
• 2142-69-0 2-bromophenyl methyl ketone 
• 18282-40-1 1-ethyl-2-iodobenzene 
• 1885-29-6 anthranilic acid nitrile 
• 133776-41-7 anthranilic acid N-methoxy-N-methylamide 
• 887144-97-0 Togni's reagent 
• 1391728-13-4 1-fluoro-3,3-dimethyl-1,3-dihydro-1λ³-benzo[d][1,2]iodaoxole 
• 1610538-81-2 3-hydroxy-1-(2-iodophenyl)-3-methylbutan-1-one 
• 98-86-2 acetophenone 
• 118-92-3 anthranilic acid 
• 88-67-5 2-Iodobenzoic acid 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 62680-67-5 2,2'-Diiod-α-methyl-cis-stilben 
• 62680-66-4 2,2'-Diiod-α-methyl-trans-stilben 
• 20914-06-1 2,2-dichloro-1-(2-iodophenyl)ethan-1-one 
• 125575-53-3 dimethyl-2',4' methoxy-6' (o-methoxyphenyl)-2 acetophenone 
• 125575-50-0 (o-acetylphenyl)-2 dimethyl-2',4' methoxy-6' acetophenone 
• 99233-97-3 2-<(2-Acetylphenyl)phenylamino>benzoesaeure-methylester 
• 78430-78-1 2-[4-(2-Acetyl-phenoxy)-phenyl]-propionic acid methyl ester 
• 99233-98-4 2-<(2-Acetylphenyl)(4-methylphenyl)amino>benzoesaeure-methylester 
• 99234-02-3 2-(2-Acetylphenylseleno)benzoesaeure-methylester 
• 144427-99-6 1-(2-iodophenyl)-1-methyloxirane 
• 117417-04-6 1-[2-(2t-bromo-vinyl-(r))-phenyl]-ethanone-⁽¹⁾ 
• 108059-69-4 2-((2-acetylphenyl)thio)benzoic acid 
• 113258-84-7 2-bromo-1-(2-iodophenyl)ethanone 
• 58164-02-6 1-(tert-butyl)-3-iodobenzene 

Relevant articles and documents

Mechanistic insight into the thermal activation of Togni's trifluoromethylation reagents

Herein we investigate the propensity of hypervalent iodine based electrophilic trifluoromethylating agents to undergo thermally induced fragmentation of the F3C-I-O motif. For the first time we are able to observe a dissociative electron transfer mechanism using mass spectroscopy techniques to generate and trap CF3 radicals. Consistent with this mechanism, alkyl radical elimination from these reagents is in full support of an intermediate cyclic iodanyl radical and a reagent-specific temperature of maximum radical production was found to correlate with reported solution phase reactivity.

Direct synthesis of 1-naphthylamines enabled by 6-endo-dig cyclization strategy using copper catalysis

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N-Heterocyclic Iod(az)olium Salts – Potent Halogen-Bond Donors in Organocatalysis

This article describes the application of N-heterocyclic iod(az)olium salts (NHISs) as highly reactive organocatalysts. A variety of mono- and dicationic NHISs are described and utilized as potent XB-donors in halogen-bond catalysis. They were benchmarked in seven diverse test reactions in which the activation of carbon- and metal-chloride bonds as well as carbonyl and nitro groups was achieved. N-methylated dicationic NHISs rendered the highest reactivity in all investigated catalytic applications with reactivities even higher than all previously described monodentate XB-donors based on iodine(I) and (III) and the strong Lewis acid BF3.

Single Cu(I)-Photosensitizer Enabling Combination of Energy-Transfer and Photoredox Catalysis for the Synthesis of Benzo[ b]fluorenols from 1,6-Enynes

An efficient, mild, and atom-economical synthesis of benzo[b]fluorenols from 1,6-enynes has been developed under photocatalytic conditions. A single P/N heteroleptic Cu(I)-photosensitizer might exhibit both energy-transfer and photoredox catalytic activities in the formation of benzo[b]fluorenols.

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Rhodium-catalyzed cycloisomerization of ester-tethered 1,6-diynes with cyclopropanol moiety leading to tetralone/exocyclic diene hybrid molecules

The rhodium-catalyzed cycloisomerization of ester-tethered 1,6-diynes bearing a cyclopropanol moiety produced tetralone/exocyclic diene hybrid molecules with thermodynamically unfavorable alkene geometry. The results of control experiments and density functional theory calculations suggest that the ester tether plays an important role in the efficiency of E/Z isomerization processes. This journal is

Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications

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One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization

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Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes

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Rapid construction of cyclopenta[: B] naphthalene frameworks from propargylic alcohol tethered methylenecyclopropanes

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