5460-32-2

Basic information

• Product Name: 3,4-DIMETHOXYIODOBENZENE
• Synonyms: 4-IODO-1,2-DIMETHOXY-BENZENE;3,4-DIMETHOXYIODOBENZENE;1,2-DIMETHOXY-4-IODOBENZENE;1-Iodo-3,4-dimethoxybenzene;Nsc25012;Benzene, 4-iodo-1,2-diMethoxy-
• CAS NO: 5460-32-2
• Molecular Formula: C₈H₉IO₂
• Molecular Weight: 264.06
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Iodine Compounds
• Mol File: 5460-32-2.mol
• Article Data: 52

Chemical Properties

• Melting Point: 35°C
• Boiling Point: 272.4°C at 760 mmHg
• Flash Point: 118.5°C
• Appearance: /
• Density: 1.6933 (estimate)
• Vapor Pressure: 0.0102mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3,4-DIMETHOXYIODOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYIODOBENZENE(5460-32-2)
• EPA Substance Registry System: 3,4-DIMETHOXYIODOBENZENE(5460-32-2)

Safety Data

• Hazardous Substances Data: 5460-32-2(Hazardous Substances Data)

Usage

General Description

3,4-Dimethoxyiodobenzene is a chemical compound that belongs to the group of iodobenzene derivatives. It is a clear, colorless to pale yellow liquid that is commonly used as a reagent in organic synthesis. 3,4-DIMETHOXYIODOBENZENE is known for its ability to undergo various chemical reactions, including Suzuki-Miyaura cross-coupling reactions and Sonogashira coupling reactions. It is also utilized as a versatile building block for the synthesis of various pharmaceuticals and biologically active compounds. Additionally, 3,4-Dimethoxyiodobenzene is considered to be an effective and mild electrophilic iodination reagent, making it a valuable tool in the field of medicinal chemistry and drug development.

InChI:InChI=1/C8H9IO2/c1-10-7-4-3-6(9)5-8(7)11-2/h3-5H,1-2H3

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 203861-62-5 2-methoxy-4-iodophenol 
• 74-88-4 methyl iodide 
• 90-05-1 2-methoxy-phenol 
• 6315-89-5 3,4-dimethoxyaniline 
• 1583285-88-4 3-(3,4-dimethoxyphenyl)-1,1,1,3,5,5,5-heptamethyltrisiloxane 
• 613-70-7 2-methoxyphenyl acetate 
• 1729-32-4 5-iodomethyl-dihydro-furan-2-one 
• 2859-78-1 4-Bromoveratrole 
• 64-17-5 ethanol 
• 7553-56-2 iodine 
• 160257-85-2 5-iodo-2-methoxyphenol 
• 77-78-1 dimethyl sulfate 
• 186581-53-3 diazomethane 

Downstream Products

• 118116-70-4 7-Diethylamino-3-(3,4-dimethoxy-phenyl)-4-methyl-chromen-2-one 
• 123251-37-6 1,2-dimethoxythioxanthen-9-one 
• 89978-46-1 4-bromo-5-iodoveratrole 
• 244037-28-3 1,2,4-trichloro-3-iodo-5,6-dimethoxybenzene 
• 51792-65-5 2-methyl-4-(3,4-dimethoxyphenyl)but-3-yn-2-ol 
• 71953-00-9 (2S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)propionic acid tert-butyl ester 
• 63914-27-2 [2-(3,4-dimethoxy-phenyl)-ethyl]-carbamic acid benzyl ester 
• 231935-01-6 ethyl 4-(3,4-dimethoxyphenyl)butanoate 
• 79238-81-6 4-[(3,4-dimethoxyphenyl)ethynyl]-1,2-dimethoxybenzene 

Relevant articles and documents

Electrochemical Generation of Hypervalent Bromine(III) Compounds

In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.

One-pot synthesis of unsymmetrical 1,3-butadiyne derivatives and their application in the synthesis of unsymmetrical 2,5-diarylthiophenes

A one-pot protocol was developed for the synthesis of unsymmetrical 1,3-butadiynes. The procedure is based on two sequential reactions: deprotection of R–C≡C–C≡C– C(Me)2OH derivatives in a retro-Favorskii reaction to furnish a terminal 1,3-butadiyne compound, which reacted with aryl iod-ides in a Sonogashira-type cross-coupling reaction catalyzed by Pd(PPh3)4 and CuI, using TBAOH as activator and toluene as solvent under reflux for 10 min. We also studied in situ thiocycli-zation of 1,3-butadiynes, leading to unsymmetrical 2,5-diaryl-thiophenes. The principal features of this method are operational simplicity, good substrate scope, very fast reaction, and high yields.

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.