6652-32-0

Basic information

• Product Name: 3,5-Dimethoxybenzyl chloride
• Synonyms: 1-(CHLOROMETHYL)-3,5-DIMETHOXYBENZENE;3,5-DIMETHOXYBENZYL CHLORIDE;3,5-Dimethyloxybenzylchloride;3,5-DiMethyoxy benzyl chloride;3,5-dimethoxybenzyl chlorid
• CAS NO: 6652-32-0
• Molecular Formula: C₉H₁₁ClO₂
• Molecular Weight: 186.64
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous;Methyl Halides;Phenyls & Phenyl-Het;Methyl Halides;Phenyls & Phenyl-Het
• Mol File: 6652-32-0.mol
• Article Data: 29

Chemical Properties

• Melting Point: 46-48 °C(lit.)
• Boiling Point: 115-118 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1631 (rough estimate)
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3,5-Dimethoxybenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dimethoxybenzyl chloride(6652-32-0)
• EPA Substance Registry System: 3,5-Dimethoxybenzyl chloride(6652-32-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6652-32-0(Hazardous Substances Data)

Usage

Description

3,5-Dimethoxybenzyl chloride is an organic compound characterized by the presence of two methoxy groups at the 3rd and 5th positions on a benzene ring, with a benzyl chloride functional group attached to the side chain. This chemical structure endows it with unique reactivity and properties, making it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
3,5-Dimethoxybenzyl chloride is used as a synthetic intermediate for the preparation of benzyl 7-(3,5-dimethoxyphenylacetoxy)octanoate, which is a precursor of curvularin. Curvularin is a natural product with potential biological activities, including anti-inflammatory and anticancer properties.
Used in Organic Synthesis:
3,5-Dimethoxybenzyl chloride is used as a reagent in the preparation of diethyl (3,5-dimethoxybenzyl) phosphonate through the Wittig-Horner reaction. This reaction is a widely used method for the synthesis of alkenes, which are important building blocks in the preparation of various organic compounds, including pharmaceuticals, agrochemicals, and materials. The introduction of the 3,5-dimethoxybenzyl moiety via this reaction can provide access to a range of novel compounds with potential applications in various fields.

Upstream product

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 

Downstream Products

• 29955-21-3 2-(3,5-dimethoxyphenyl)-1-phenylethanone 
• 331858-80-1 C₁₄H₂₁NO₃ 
• 232275-43-3 4-(3,5-dimethoxybenzyl)thiomorpholine 
• 151855-75-3 acetylamino-(3,5-dimethoxy-benzyl)-malonic acid diethyl ester 
• 1310538-28-3 C₁₉H₂₂O₅ 
• 1310538-29-4 C₁₉H₂₂O₅ 
• 1310538-30-7 C₁₈H₂₀O₄ 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 94608-23-8 (Z)-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene 
• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 441351-32-2 (Z)-4-hydroxy-3',5'-dimethoxystilbene 
• 80715-09-9 (E)-3,3',5,5'-tetramethoxystilbene 
• 125910-10-3 1,2-bis(3,5-dimethoxyphenyl)ethylene 

Relevant articles and documents

Stereoselective Total Synthesis of (-)-(2 S,4 R)-3′-Methoxyl Citreochlorol: Preparation and Use of New Proline-Based Auxiliary for Asymmetric Acetate Aldol Reaction

The first stereoselective total synthesis of (-)-(2S,4R)-3′-methoxy citreochlorol and (-)-(2S,4S)-3′-methoxy citreochlorol is demonstrated. A proline-based imidazolidinone was synthesized and used as chiral auxiliary for asymmetric acetate aldol reaction to generate initial chirality in the targeted molecule. Geminal dichloromethane functionality was introduced by the addition of in situ generated dichloromethyllithium to Weinreb's amide functional group.

Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase

Stilbenoids are important components of foods (e.g., peanuts, grapes, various edible berries), beverages (wine, white tea), and medicinal plants. Many publications have described the anti-inflammatory potential of stilbenoids, including the widely known trans-resveratrol and its analogues. However, comparatively little information is available regarding the activity of their prenylated derivatives. One new prenylated stilbenoid (2) was isolated from Artocarpus altilis and characterized structurally based on 1D and 2D NMR analysis and HRMS. Three other prenylated stilbenoids were prepared synthetically (9-11). Their antiphlogistic potential was determined by testing them together with known natural prenylated stilbenoids from Macaranga siamensis and Artocarpus heterophyllus in both cell-free and cell assays. The inhibition of 5-lipoxygenase (5-LOX) was also shown by simulated molecular docking for the most active stilbenoids in order to elucidate the mode of interaction between these compounds and the enzyme. Their effects on the pro-inflammatory nuclear factor-κB (NF-κB) and the activator protein 1 (AP-1) signaling pathway were also analyzed. The THP1-XBlue-MD2-CD14 cell line was used as a model for determining their anti-inflammatory potential, and lipopolysaccharide (LPS) stimulation of Toll-like receptor 4 induced a signaling cascade leading to the activation of NF-κB/AP-1. The ability of prenylated stilbenoids to attenuate the production of pro-inflammatory cytokines tumor necrosis factor-α (TNF-α) and interleukin-1β (IL-1β) was further evaluated using LPS-stimulated THP-1 macrophages.

Preparation method of resveratrol

The invention discloses a preparation method of resveratrol. The preparation method comprises that (1), 3, 5-dimethoxybenzhydrol is chloroformed under the action of triphosgene to form 3, 5-dimethoxybenzyl chloride, (2), 3, 5-dimethoxybenzyl chloride reacts with triphenylphosphine to produce phosphorus ylide, (3), phosphorus ylide and p-methoxybenzaldehyde form a cis-trans-isomer mixture of 3, 4',5-trimethoxydistyrene under the action of lithium hydroxide, (4), 3, 4', 5-trimethoxystilbene, aluminum and iodine are added to acetonitrile, the mixture is cooled to the room temperature so that yellow solids are separated, the yellow solids are filtered, the filtrate acetonitrile is directly recovered and recycled, 6N hydrochloric acid and ethyl acetate are added into the filter cake, the mixture is stood for layering, wherein the water layer contains ethyl acetate extract, the organic phases are mixed, the organic phases are washed through a saturated salt solution, anhydrous sodium sulfate is dried and filtered, the solvent is removed in vacuum through a water pump, and the organic phase is recrystallized through ethanol and water so that resveratrol is obtained. The preparation method utilizes easily available raw materials, is easy to operate and control, is environmentally friendly, produces easily purified products, has a high yield and is suitable for industrial production.