5438-36-8

Basic information

• Product Name: 5-IODOVANILLIN
• Synonyms: TIMTEC-BB SBB006927;OTAVA-BB BB0107930009;4-hydroxy-3-iodo-5-methoxy-benzaldehyd;AKOS B004179;AKOS BBS-00004640;5-IODOVANILLIN;4-HYDROXY-5-IODO-3-METHOXYBENZALDEHYDE;4-HYDROXY-3-IODO-5-METHOXYBENZALDEHYDE
• CAS NO: 5438-36-8
• Molecular Formula: C₈H₇IO₃
• Molecular Weight: 278.04
• EINECS: 226-617-7
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C8;Carbonyl Compounds
• Mol File: 5438-36-8.mol
• Article Data: 43

Chemical Properties

• Melting Point: 183-185 °C(lit.)
• Boiling Point: 304℃
• Flash Point: 138℃
• Appearance: Light yellow/Fine Crystalline Powder
• Density: 1.909
• Vapor Pressure: 0.000498mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 6.34±0.23(Predicted)
• Sensitive: Light Sensitive
• BRN: 2049762
• CAS DataBase Reference: 5-IODOVANILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: 5-IODOVANILLIN(5438-36-8)
• EPA Substance Registry System: 5-IODOVANILLIN(5438-36-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5438-36-8(Hazardous Substances Data)

Usage

Description

5-Iodovanillin is a light yellow fine crystalline powder, which is a derivative of vanillin with an added iodine atom at the 5th position. This modification gives it unique chemical properties that make it useful in various applications.

Uses

Used in Chemical Synthesis:
5-Iodovanillin is used as a synthetic intermediate for the production of various compounds. Its chemical properties allow it to be a versatile building block in the synthesis of different molecules.
Used in Pharmaceutical Industry:
5-Iodovanillin is used as a key component in the synthesis of the platelet activating factor (PAF) antagonist L-659,989. This application is significant because PAF antagonists have potential therapeutic uses in treating various conditions, such as asthma, allergies, and cardiovascular diseases.
Used in Analytical Chemistry:
5-Iodovanillin has been used in the characterization of 5-Iodoacetovanillone, which is another compound with potential applications in various fields. This use highlights the importance of 5-Iodovanillin in the analysis and understanding of related chemical structures.

Preparation

synthesize 5-iodovanillin from vanillin

InChI:InChI=1/C8H7IO3/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-4,11H,1H3

Upstream product

• 71017-38-4 N-iodo-benzamidine 
• 121-33-5 vanillin 
• 37987-21-6 4-hydroxy-3-iodo-5-methoxybenzyl alcohol 
• 89942-36-9 2-iodo-4-hydroxy-3-methoxybenzaldehyde 

Downstream Products

• 109961-94-6 2-iodo-6-methoxy-4-methoxymethyl-phenol 
• 3934-87-0 5-hydroxyvanillin 
• 32024-15-0 3,4-dimethoxy-5-iodobenzaldehyde 
• 73664-55-8 4-hydroxy-3-iodo-5-methoxy-benzaldehyde-oxime 
• 486994-14-3 4-(acetyloxy)-3-iodo-5-methoxybenzaldehyde 
• 73664-56-9 4-hydroxy-3-iodo-5-methoxy-benzaldehyde-semicarbazone 
• 134-96-3 syringic aldehyde 
• 6958-25-4 5-Iod-vanillin-octadecylthiosemicarbazon 
• 23561-45-7 4-<4-Acetoxy-3-jod-5-methoxy-benzyliden>-2-methyl-oxazolon-(5) 
• 113790-67-3 1-(3-methoxy-5-methylsulfonyl-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione 
• 152489-33-3 Phenylsulfanyl-acetic acid [1-(4-hydroxy-3-iodo-5-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide 
• 85418-20-8 Hydroxy-(4-hydroxy-3-iodo-5-methoxy-phenyl)-acetonitrile 

Relevant articles and documents

An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine

An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.

Regioselective Halogenation of Arenes and Heterocycles in Hexafluoroisopropanol

Regioselective halogenation of arenes and heterocycles with N-halosuccinimides in fluorinated alcohols is disclosed. Under mild condition reactions, a wide diversity of halogenated arenes are obtained in good yields with high regioselectivity. Additionally, the versatility of the method is demonstrated by the development of one-pot sequential halogenation and halogenation-Suzuki cross-coupling reactions.

Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues

Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99% ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.