5417-17-4

Basic information

• Product Name: 2-Chloroveratraldehyde
• Synonyms: TIMTEC-BB SBB003539;LABOTEST-BB LT01147597;2-CHLORO-3,4-DIMETHOXYBENZALDEHYDE;2-CHLOROVERATRALDEHYDE;2-Chloro-3,4-dimethoxybenzalde;2-CHLORO-3,4-DIMETHOXYBENZALDE 98%;2-Chloro-3,4-dimethoxybenzaldehyde,98%;2‐Chlorovanillin methyl ether
• CAS NO: 5417-17-4
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.62
• EINECS: 226-515-2
• Product Categories: Benzaldehyde;(intermediate of fenoldopam);Fenoldopam
• Mol File: 5417-17-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 300.9 °C at 760 mmHg
• Flash Point: 130.8 °C
• Appearance: beige-yellow to beige crystalline powder
• Density: 1.245 g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Sensitive: Air Sensitive
• BRN: 2109344
• CAS DataBase Reference: 2-Chloroveratraldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroveratraldehyde(5417-17-4)
• EPA Substance Registry System: 2-Chloroveratraldehyde(5417-17-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5417-17-4(Hazardous Substances Data)

Usage

Description

2-Chloroveratraldehyde, also known as 2-Chloro-3,4-dimethoxybenzaldehyde, is a beige-yellow to beige crystalline powder with unique chemical properties. It is a valuable compound in the field of organic synthesis and pharmaceutical research due to its versatile reactivity and potential applications.

Uses

Used in Pharmaceutical Synthesis:
2-Chloroveratraldehyde is used as a reagent for the synthesis of the human TLR4 agonist euodenine A. This application is significant because TLR4 agonists have potential therapeutic applications in the treatment of various diseases, including cancer and inflammatory disorders.
Used in the Synthesis of PDE10A Inhibitors:
2-Chloroveratraldehyde is also used as a reagent in the synthesis of novel 2-methoxyacylhydrazones, which are potent and selective PDE10A inhibitors. These inhibitors have demonstrated activity in animal models of schizophrenia, making them a promising avenue for the development of new treatments for this mental health disorder.

InChI:InChI=1/C9H9ClO3/c1-12-7-4-3-6(5-11)8(10)9(7)13-2/h3-5H,1-2H3

Upstream product

• 93983-14-3 2-chloro-3,4-dimethoxybenzyl chloride 
• 82668-20-0 2-Chlorovanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 37687-57-3 2-chloro-3-hydroxy-4-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 68-12-2 N,N-dimethyl-formamide 
• 459410-39-0 2-chloro-1-iodo-3,4-dimethoxy-benzene 
• 52009-53-7 2-chloro-3,4-dimethoxy-benzoic acid 
• 621-59-0 isovanillin 
• 90282-99-8 3-chloro-1,2-dimethoxybenzene 
• 74-88-4 methyl iodide 
• 584-08-7 potassium carbonate 
• 70946-18-8 N,N-diethyl-3,4-dimethoxybenzamide 
• 1228657-94-0 C₁₃H₁₈ClNO₃ 

Downstream Products

• 119749-94-9 2-chloro-3,4-dimethoxy-1-(2-nitro-cis-propenyl)-benzene 
• 41122-35-4 (E)-2-chloro-3,4-dimethoxy-1-(2-nitrovinyl)benzene 
• 859739-05-2 1-(2-chloro-3,4-dimethoxy-phenyl)-2-nitro-ethanol 
• 37687-57-3 2-chloro-3-hydroxy-4-methoxybenzaldehyde 
• 52009-53-7 2-chloro-3,4-dimethoxy-benzoic acid 
• 99854-17-8 2-chloro-3,4-dimethoxy-trans-cinnamic acid 
• 32864-11-2 2-Chloro-3,4-dihydroxybenzaldehyde 
• 93983-13-2 2-chloro-3,4-dimethoxybenzyl alcohol 
• 67287-37-0 N-(2-Hydroxy-2-phenethyl)-N-<2-(2'-chlor-3',4'-dimethoxyphenyl)-ethyl>-amin 
• 67287-38-1 6-chloro-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Relevant articles and documents

Chemoselective zinc/HCl reduction of halogenated β-nitrostyrenes: Synthesis of halogenated dopamine analogues

A detailed account regarding the synthesis of 2- and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

Schwartz Reagents: Methods of In Situ Generation and Use

Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.

Aryl-substituted cycloalkanes and cycloalkenes and herbicidal use thereof

Disclosed are herbicidal aryl substituted cycloalkyl and aryl substituted cycloalkenyl compounds, herbicidal compositions, and herbicidal use of the compounds and compositions. The aryl substituent is selected from substituted phenyl, unsubstituted or substituted five-membered heterocycle, and unsubstituted or substituted six-membered heterocycle.