91718-20-6

Basic information

• Product Name: 3-IODO-4-METHOXYBIPHENYL
• Synonyms: 3-IODO-4-METHOXYBIPHENYL;3-Iodo-4-methoxy-1,1′-biphenyl
• CAS NO: 91718-20-6
• Molecular Formula: C₁₃H₁₁IO
• Molecular Weight: 310.13
• Mol File: 91718-20-6.mol

Chemical Properties

• Melting Point: 89-91°C
• Boiling Point: 378°Cat760mmHg
• Flash Point: 182.4°C
• Appearance: /
• Density: 1.544g/cm³
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 3-IODO-4-METHOXYBIPHENYL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODO-4-METHOXYBIPHENYL(91718-20-6)
• EPA Substance Registry System: 3-IODO-4-METHOXYBIPHENYL(91718-20-6)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 91718-20-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-IODO-4-METHOXYBIPHENYL is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the creation of a range of organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, 3-IODO-4-METHOXYBIPHENYL is utilized as an intermediate, playing a crucial role in the development of new drugs and pharmaceuticals due to its unique chemical properties.
Used in Medicine:
3-IODO-4-METHOXYBIPHENYL is used as a precursor in the synthesis of medicinal compounds, contributing to the advancement of treatments for various diseases and conditions.
Used in Agriculture:
In agricultural applications, 3-IODO-4-METHOXYBIPHENYL is employed for its potential role in the development of agrochemicals, which can enhance crop protection and yield.
Used in Material Science:
3-IODO-4-METHOXYBIPHENYL is used in material science for its potential to contribute to the creation of new materials with specific properties, such as those with enhanced stability or reactivity.

InChI:InChI=1/C13H11IO/c1-15-13-8-7-11(9-12(13)14)10-5-3-2-4-6-10/h2-9H,1H3

Upstream product

• 613-37-6 4-methoxylbiphenyl 
• 92-69-3 4-Phenylphenol 
• 71031-48-6 2-iodo-4-phenylphenol 
• 74-88-4 methyl iodide 
• 21702-84-1 2,4-dibromoanisole 
• 177490-75-4 (5-Bromo-2-methoxy-phenyl)-chloromethoxymethyl-dimethyl-silane 
• 98-80-6 phenylboronic acid 

Downstream Products

• 71031-48-6 2-iodo-4-phenylphenol 

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.

Entry to 1,2,3,4-Tetrasubstituted Arenes through Addressing the " Meta Constraint" in the Palladium/Norbornene Catalysis

Arenes with four different contiguous substituents, i.e. 1,2,3,4-tetrasubstituted arenes, are commonly found in bioactive compounds, but they are nontrivial to access via conventional methods. Through addressing the "meta constraint" in the palladium/norbornene (Pd/NBE) cooperative catalysis, which is the difficulty of tolerating a sizable meta substituent in aryl halide substrates, here a modular and regioselective approach is realized for preparing 1,2,3,4-tetrasubstituted arenes. One key is the use of a C2-amide-substituted NBE, and a combined experimental and computational study reveals its role in promoting the NBE insertion and the ortho C-H metalation steps. The scope is broad: A variety of electrophiles and nucleophiles could be introduced to the ortho and ipso positions, respectively, with 1,4-disubstituted aryl halides, leading to diverse unsymmetrical contiguous tetrasubstituted arenes. Application of this approach has been demonstrated in streamlined syntheses of several bioactive compounds.

Protecting Group-Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions

Being able to utilize a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalization of complex organic molecules. However, protecting groups that have the ability to influence reaction regi

One-pot ortho-amination of aryl C-H bonds using consecutive iron and copper catalysis

A one-pot approach for ortho-coupling of arenes with non-actived N-nucleophiles has been developed using sequential iron and copper catalysis. Regioselective ortho-activation of anisoles, anilines and phenols was achieved through iron(iii) triflimide catalysed iodination, followed by a copper(i)-catalysed, ligand-assisted coupling reaction with N-heterocycle, amide and sulfonamide-based nucleophiles. The synthetic utility of this one-pot, two-step method for the direct amination of ortho-aryl C-H bonds was demonstrated with the late-stage functionalisation of 3,4-dihydroquinolin-2-ones. This allowed the preparation of a TRIM24 bromodomain inhibitor and a series of novel analogues.

Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction

A method for attaching haloarylsilanes to polymer support was developed. The polymer bound arylhalide were reacted with a variety of ArB(OH)2 under the Suzuki cross-coupling reaction conditions and the coupled resins were cleaved by different electrophiles to give ipso-substitution products in good yields.