52692-09-8

Basic information

• Product Name: 4-Iodo-2-nitroanisole
• Synonyms: 4-IODO-2-NITROANISOLE;4-iodo-1-methoxy-2-nitrobenzene
• CAS NO: 52692-09-8
• Molecular Formula: C₇H₆INO₃
• Molecular Weight: 279.03
• Mol File: 52692-09-8.mol

Chemical Properties

• Melting Point: 96-98°C
• Boiling Point: 330.8 °C at 760 mmHg
• Flash Point: 153.9 °C
• Appearance: /
• Density: 1.893g/cm³
• Vapor Pressure: 0.000313mmHg at 25°C
• Refractive Index: 1.629
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Iodo-2-nitroanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodo-2-nitroanisole(52692-09-8)
• EPA Substance Registry System: 4-Iodo-2-nitroanisole(52692-09-8)

Safety Data

• Statements: 23/24/25
• Safety Statements: 36/37-45
• Hazardous Substances Data: 52692-09-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H6INO3/c1-12-7-3-2-5(8)4-6(7)9(10)11/h2-4H,1H3

Upstream product

• 91-23-6 2-Nitroanisole 
• 696-62-8 para-iodoanisole 
• 364-75-0 1-fluoro-4-iodo-2-nitro-benzene 
• 124-41-4 sodium methylate 
• 186581-53-3 diazomethane 
• 21784-73-6 4-iodo-2-nitrophenol 
• 7697-37-2 nitric acid 
• 352-34-1 4-fluoro-1-iodobenzene 
• 364-76-1 4-Fluoro-3-nitroaniline 
• 4920-80-3 3-methoxy-2-nitrobenzoic acid 
• 577-72-0 4-methoxy-3-nitroaniline 

Downstream Products

• 119-27-7 2,4-dinitroanisole 
• 77770-09-3 3-amino-4-methyloxyphenyliodide 
• 851218-51-4 ethyl 3-(4-methoxy-3-nitrophenyl)propynoate 
• 1242653-18-4 5-(cyclohexylidene(4-methoxy-3-nitrophenyl)methyl)-1,2,3-trimethoxybenzene 
• 1242653-21-9 5-(cyclopentylidene(4-methoxy-3-nitrophenyl)methyl)-1,2,3-trimethoxybenzene 
• 1242653-31-1 1,2,3-trimethoxy-5-(1-(4-methoxy-3-nitrophenyl)-2-methylprop-1-en-1-yl)benzene 
• 1070195-65-1 1-(4'-methoxy-3'-nitrophenyl)-1-(3'',4'',5''-trimethoxyphenyl)ethylene 
• 1334752-47-4 2-methoxy-5-(4,5,6-trimethoxy-indol-1-yl)-phenylamine 
• 1370263-13-0 1,2,3-trimethoxy-5-[(4-methoxy-3-nitrophenyl)sulfanyl]benzene 
• 1370263-14-1 2-methoxy-5-[(3,4,5-trimethoxyphenyl)sulfanyl]aniline 
• 1608474-81-2 3,4,5-trimethoxy-N-(4-methoxy-3-nitrophenyl)-N-methylaniline 
• 1608474-82-3 4-methoxy-N-methyl-N-(3,4,5-trimethoxyphenyl)benzene-1,3-diamine 

Relevant articles and documents

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

Method for synthesizing m-iodonitrobenzene compound

Provided is a method for synthesizing m-iodonitrobenzene; in the presence of oxygen gas, a palladium catalyst, a copper additive, a bismuth reagent and potassium phosphate, an o-nitrobenzoic acid compound and metal iodide are subjected to a substitution reaction in an organic solvent to form a corresponding m-iodonitrobenzene compound, wherein a metal in the metal iodide is an alkali metal or an alkaline earth metal. The method has obvious advantages of cheap and easily obtained reaction raw materials (including o-nitrobenzoic acid and MI), small amount of the metal catalyst, minimum environmental pollution with oxygen gas as an oxidant, good tolerance on various functional groups on an aromatic ring and the like. The method can be widely applied in the fields of synthesis of drugs, materials, natural products and the like in industrial and academic circles.

Transition-metal-free hydrogenation of aryl halides: From alcohol to aldehyde

A transition-metal-and catalyst-free hydrogenation of aryl halides, promoted by bases with either aldehydes or alcohols, is described. One equivalent of benzaldehyde affords an equal yield as that of 0.5 equiv of benzyl alcohol. The kinetic study reveals that the initial rate of PhCHO is much faster than that of BnOH, in the ratio of nearly 4:1. The radical trapping experiments indicate the radical nature of this reaction. Based on the kinetic study, trapping and KIE experiments, and control experiments, a tentative mechanism is proposed. As a consequence, a wide range of (hetero)aryl iodides and bromides were efficiently reduced to their corresponding (hetero)arenes. Thus, for the first time, aldehydes are directly used as hydrogen source instead of other well-established alcohol-hydrogen sources.

Gold(I)-catalyzed iodination of arenes

A wide variety of electron-rich arenes were efficiently converted into the corresponding iodinated compounds via a gold(I)-catalyzed reaction under mild conditions. Georg Thieme Verlag Stuttgart. New York.

Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity

We have devised a procedure for the synthesis of analogs of combretastatin A-4 (CA-4) containing sulfur and selenium atoms as spacer groups between the aromatic rings. CA-4 is well known for its potent activity as an inhibitor of tubulin polymerization, a

Negishi cross-coupling reaction as a route to isocombretastatins

A series of isocombretastatins A has been synthesized by a new method based on the Negishi cross-coupling reaction in 19-84% yields. Five of the synthesized compounds exhibit high cytotoxic activity in nanomolar concentrations (IC50 = 1-100 n) towards Jurkat, K562, Colo357, and A549 cell lines. Georg Thieme Verlag Stuttgart · New York.

Novel water-soluble anticancer agents derived from 4-arylcoumarins

Novel 4-arylcoumarin derivatives were obtained. They are water-soluble analogs of the well-known anticancer drug combretastatin A-4. The key step of the synthesis involves the Suzuki-Miyaura cross-coupling. The water-soluble salts obtained exhibit conside

New method of synthesis and biological evaluation of some combretastatin A-4 analogues

A series of novel combretastatin A-4 analogues was synthesized in 36-64% yields by Negishi cross-coupling reaction under mild conditions. The prepared compounds exhibit good cytotoxicity against HBL100 epithelial cell lines (IC50=0.022-10.31 ). Georg Thieme Verlag Stuttgart · New York.

Aromatic nitration under neutral conditions using N-bromosuccinimide/ silver(I) nitrate

The use of N-bromosuccinimide and silver nitrate as a convenient reagent system for the nitration of aromatic compounds under neutral and environmentally safer reaction conditions is described.

Nitration of aromatic compounds under neutral conditions using the Ph 2PCl/I2/AgNO3 reagent system

Aromatic compounds were nitrated efficiently under essentially neutral conditions by employing Ph2PCl in the presence of I2 and AgNO3. This method minimizes waste products compared to traditional methods and gives the corresponding mononitro derivatives in good to excellent yields in dichloromethane at room temperature.