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
• Article Data: 32

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

Chemical Properties

Clear yellow liquid

Uses

2′-Iodoacetophenone (2-Iodoacetophenone) may be used in the synthesis of:indene derivativesdi-(o-acetylphenyl)acetyleneindenol derivative

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.

General Description

2′-Iodoacetophenone is a halogenated aromatic ketone.

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

Upstream product

• 609-67-6 2-Iodobenzoyl chloride 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 551-93-9 2-aminoacetophenone 
• 105-53-3 diethyl malonate 
• 98-86-2 acetophenone 
• 18282-40-1 1-ethyl-2-iodobenzene 
• 26260-02-6 2-iodobenzaldehyde 
• 187939-66-8 1-tert-butylperoxy-3,3-dimethyl-1H-1,2-benziodoxole 
• 122752-70-9 2-iodo-α-methyl-benzenemethanol 
• 2142-69-0 2-bromophenyl methyl ketone 
• 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 

Downstream Products

• 125575-51-1 (p-acetophenyl)-2 dimethyl2',4' methoxy-6' acetophenone 
• 125575-50-0 (o-acetylphenyl)-2 dimethyl-2',4' methoxy-6' acetophenone 
• 27513-86-6 1-(1,1-Diethoxy-ethyl)-2-iodo-benzene 
• 452962-75-3 1-(2-iodophenyl)-2-phenoxyethanone 
• 236737-79-4 ethyl (Z)-3-(2-iodophenyl)but-2-enoate 
• 236737-78-3 ethyl (E)-3-(2-iodophenyl)but-2-enoate 
• 380225-74-1 7-acetoxy-3-hydroxy-1-(2-iodophenyl)non-8-en-1-one 
• 92060-18-9 2-(2-iodophenyl)-1H-indole 
• 21503-19-5 1-(2-(phenylthio)phenyl)ethan-1-one 
• 58164-02-6 1-(tert-butyl)-3-iodobenzene 
• 137103-78-7 1-(2-(pyridin-2-yl)phenyl)ethan-1-one 
• 923722-94-5 N-(2-acetylphenyl)-3-methylbenzamide 

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.

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.

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.]