77287-58-2

Basic information

• Product Name: 2-Iodo-5-methoxybenzaldehyde
• Synonyms: 2-Iodo-5-methoxybenzaldehyde;2-Iodo-5-methoxybenzaldehyd
• CAS NO: 77287-58-2
• Molecular Formula: C₈H₇IO₂
• Molecular Weight: 262.04445
• Product Categories: Building Blocks;C2 to C8;Chemical Synthesis;Ethers;New Products for Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;aldehyde| alkyl Iodine
• Mol File: 77287-58-2.mol

Chemical Properties

• Melting Point: 110-115℃
• Appearance: White to off-white to yellow/Solid
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: 2-Iodo-5-methoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodo-5-methoxybenzaldehyde(77287-58-2)
• EPA Substance Registry System: 2-Iodo-5-methoxybenzaldehyde(77287-58-2)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• WGK Germany: 3
• Hazardous Substances Data: 77287-58-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodo-5-methoxybenzaldehyde is used as an intermediate in the synthesis of pharmaceuticals for its ability to undergo various organic transformations, making it a versatile building block in the development of new drugs.
Used in Organic Synthesis:
2-Iodo-5-methoxybenzaldehyde is used as a starting material for the synthesis of biologically active compounds due to its potential to participate in nucleophilic substitution and aromatic coupling reactions, contributing to the creation of novel organic compounds with potential applications.

Upstream product

• 6971-51-3 3-methoxybenzyl alcohol 
• 54413-93-3 2-iodo-5-methoxybenzoic acid 
• 6705-03-9 2-Amino-5-methoxybenzoic acid 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 150192-39-5 2-Bromo-5-methoxybenzyl alcohol 
• 591-31-1 3-methoxy-benzaldehyde 
• 139557-96-3 (2-iodo-5-methoxyphenyl)methanol 

Downstream Products

• 132901-31-6 4,4′-dimethoxy[1,1′-biphenyl]-2,2′-dicarbaldehyde 
• 118545-81-6 4,4'-bis-(2H-chromen-2-one) 
• 1235340-59-6 C₁₇H₁₄O₂S 
• 1416476-21-5 C₁₀H₁₁IO 
• 1416476-25-9 C₁₀H₁₁IO 

Relevant articles and documents

INHIBITORS OF PURINE NUCLEOSIDE PHOSPHORYLASE - SYNTHESIS AND USE THEREOF FOR TREATMENT OF T-CELL ACUTE LYMPHOBLASTIC LEUKEMIA AND LYMPHOMA

The present invention relates to new compounds of general formula I, their synthesis, their pharmaceutically acceptable salts, and their use in treatment of T-cell acute lymphoblastic leukemia and lymphoma.

Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process

A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.

One-pot synthesis of hypervalent diaryl(iodo)bismuthanes from o-carbonyl iodoarenes by zincation

Diaryl(iodo)bismuthanes possessing a hypervalent C=O???Bi-I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds under mild reaction conditions that do not need low temperature control. Furthermore, no intermediate triarylbismuthane precursor for the hypervalent iodobismuthane is necessary.

Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon. The electronic effects are studied in other contexts, including hydroacyloxylation and hydroamination, and similar trends in directionality are predominant although not uniformly observed.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Cu-Catalyzed Enantioselective Ring Opening of Cyclic Diaryliodoniums toward the Synthesis of Chiral Diarylmethanes

A Cu-catalyzed enantioselective desymmetrizing ring-opening reaction of six-membered cyclic diaryliodonium salts with carboxylic acids or thioacids is reported for the facile access to chiral diarylmethanes. A Cu/[cyclopropyl bis(oxazoline)] catalyst well

Palladium-Catalyzed, Norbornene-Mediated, ortho-Amination ipso-Amidation: Sequential C-N Bond Formation

A palladium-catalyzed, norbornene-mediated ortho- and ipso-C-N bond-forming Catellani reaction is reported. This reaction proceeds through a sequential intermolecular amination followed by intramolecular cyclization of a tethered amide. The products, ortho-aminated dihydroquinolinones, were generated in moderate to good yields and are present in bioactive molecules. This work highlights the challenge of competing intra- vs intermolecular palladium-catalyzed processes.

Total synthesis of selaginpulvilins A and C

An efficient formal total synthesis of two compounds from the selaginpulvilin family of natural products, selaginpulvilin A and C, has been successfully achieved. The tetradehydro Diels-Alder (TDDA) reaction between an enyne and alkyne has been utilized for the creation of the necessary fluorene skeleton. Attempts at the conversion of selaginpulvilin A to selaginpulvilin B, F and H were unsuccessful.

F- Nucleophilic-Addition-Induced [3 + 2] Annulation: Direct Access to CF3-Substituted Indenes

An efficient [3 + 2] annulation of (2,2-difluorovinyl)-2-iodoarenes and internal alkynes was developed for the synthesis of 1-(trifluoromethyl)-1H-indenes. The success of this strategy hinges upon a well-balanced process for the generation of two transient reactive species, specifically trifluoroethylsilver and alkenylpalladium intermediates, in the same molecule, as well as a smooth transmetalation step, which delicately joins together these two different metallic intermediates.