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

Uses

3,5-Dimethoxybenzyl chloride was used in preparation of benzyl 7-(3,5-dimethoxyphenylacetoxy)octanoate, a precursor of curvularin. It was also used in the preparation of diethyl (3,5-dimethoxybenzyl) phosphonate via Wittig-Horner reaction.

Upstream product

• 17275-82-0 ethyl 3,5-dimethoxybenzoate 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 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 
• 168697-62-9 1-(3,5-dimethoxyphenyl)-2-hydroxytridecane 
• 185249-89-2 2-(3,5-dimethoxyphenyl)-1-(4'-methyoxyphenyl)ethan-1-ol 
• 185249-90-5 1-(3,4-dimethoxyphenyl)-2-(3',5'-dimethoxyphenyl)ethan-1-ol 
• 163683-23-6 1-(3,5-dimethoxyphenyl)-heptadecane-2-one 
• 185249-85-8 2-(3,5-dimethoxyphenyl)-1-phenylethan-1-ol 
• 232275-43-3 4-(3,5-dimethoxybenzyl)thiomorpholine 
• 21956-56-9 (E)-3,5-dimethoxystilbene 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 114701-80-3 (E)-5-(3,5-dimethoxystyryl)benzo[d][1,3]dioxole 
• 387372-17-0 Resveratrol-3-O-glucuronide 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 42206-94-0 triacetyl-trans-resveratrol 
• 861446-14-2 (E)-4-(3-acetoxy-5-hydroxystyryl)phenyl acetate 

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.

Parallel in vitro and in silico investigations into anti-inflammatory effects of non-prenylated stilbenoids

Stilbenoids represent a large group of bioactive compounds, which occur in food and medicinal plants. Twenty-five stilbenoids were screened in vitro for their ability to inhibit COX-1, COX-2 and 5-LOX. Piceatannol and pinostilbene showed activity comparable to the zileuton and ibuprofen, respectively. The anti-inflammatory potential of stilbenoids was further evaluated using THP-1 human monocytic leukemia cell line. Tests of the cytotoxicity on the THP-1 and HCT116 cell lines showed very low toxic effects. The tested stilbenoids were evaluated for their ability to attenuate the LPS-stimulated activation of NF-κB/AP-1. Most of the tested substances reduced the activity of NF-κB/AP-1 and later attenuated the expression of TNF-α. The effects of selected stilbenoids were further investigated on inflammatory signaling pathways. Non-prenylated stilbenoids regulated attenuation of NF-?B/AP-1 activity upstream by inhibiting the phosphorylation of MAPKs. A docking study used to in silico analyze the tested compounds confirmed their interaction with NF-?B, COX-2 and 5-LOX.

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.