82504-06-1

Basic information

• Product Name: 3-Iodo-4-methoxybenzonitrile
• Synonyms: 3-Iodo-4-methoxybenzonitrile;4-Cyano-2-iodoanisole, 3-Iodo-p-anisonitrile
• CAS NO: 82504-06-1
• Molecular Formula: C₈H₆INO
• Molecular Weight: 259.04381
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Iodine Compounds
• Mol File: 82504-06-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 320.7±32.0 °C(Predicted)
• Appearance: /
• Density: 1.82±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-Iodo-4-methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-4-methoxybenzonitrile(82504-06-1)
• EPA Substance Registry System: 3-Iodo-4-methoxybenzonitrile(82504-06-1)

Safety Data

• Hazardous Substances Data: 82504-06-1(Hazardous Substances Data)

Upstream product

• 2296-23-3 2-iodo-4-cyanophenol 
• 74-88-4 methyl iodide 
• 5399-03-1 2-iodo-1-methoxy-4-nitrobenzene 
• 143-33-9 sodium cyanide 
• 874-90-8 4-methoxybenzonitrile 
• 77-78-1 dimethyl sulfate 
• 767-00-0 4-cyanophenol 

Downstream Products

• 565203-80-7 3-benzo[1,3]dioxol-5-yl-4-methoxy-benzonitrile 
• 565203-83-0 3',5'-dichloro-6-methoxy-biphenyl-3-carbonitrile 
• 152775-45-6 4-methoxy-3,5-dimethylbenzonitrile 
• 82504-10-7 Trimethylsilanyl-acetic acid (2R,4S,9aR)-4-(5'-formyl-4,5,2'-trimethoxy-biphenyl-2-yl)-octahydro-quinolizin-2-yl ester 
• 82504-08-3 6,4',5'-Trimethoxy-2'-((4S,9aR)-2-oxo-octahydro-quinolizin-4-yl)-biphenyl-3-carbonitrile 
• 82504-09-4 2'-((2R,4S,9aR)-2-Hydroxy-octahydro-quinolizin-4-yl)-6,4',5'-trimethoxy-biphenyl-3-carbaldehyde 
• 565203-90-9 trifluoro-methanesulfonic acid 2-benzo[1,3]dioxol-5-yl-4-cyano-phenyl ester 
• 565203-97-6 3-benzo[1,3]dioxol-5-yl-4-trimethylsilanylethynyl-benzonitrile 
• 565204-04-8 3-benzo[1,3]dioxol-5-yl-4-ethynyl-benzonitrile 
• 450842-25-8 3-(1,3-benzodioxol-5-yl)-4-hydroxybenzonitrile 

Relevant articles and documents

Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.

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.

The element effect in nucleophilic aromatic photosubstitution (S N2Ar*)

Photoreactions of 4-nitroanisole and the 2-halo-4-nitroanisoles (halogen == F, Cl, Br, I) with NaCN have been investigated. 4-Nitroanisole gave a novel, stable nitronate ion adduct (74%) with cyanide. For the five compounds, we report product distributions, Stern-Volmer kinetic plots, triplet lifetimes, and triplet yields, which afford rate constants for attack by the cyanide ion. Cyanide attack on the fluoride is diffusion controlled; the relative rates for attack at F, Cl, Br, and I are 27:2:2:1, respectively.