824-98-6

Basic information

• Product Name: 3-Methoxybenzyl chloride
• Synonyms: (3-Methoxyphenyl)methyl chloride;a-Chloro-m-methoxytoluene;1-Methoxy-3-(chloromethyl)benzene;3-Methoxy-1-(chloromethyl)benzene;3-Methoxybenzyl chloride,97%;3-Methoxybenzyl chlo;3-Methoxybenzyl chloride, 97% 5GR;1-(Chloromethyl)-3-methoxybenzene, 3-(Chloromethyl)phenyl methyl ether, 3-(Chloromethyl)anisole
• CAS NO: 824-98-6
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• EINECS: 212-541-1
• Product Categories: Chemical intermediate for Sarpogrelate hydrochloride
• Mol File: 824-98-6.mol
• Article Data: 32

Chemical Properties

• Melting Point: 101.67°C
• Boiling Point: 124 °C13 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: clear colorless to light yellow liquid
• Density: 1.078 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0284mmHg at 25°C
• Refractive Index: n20/D 1.544(lit.)
• Storage Temp.: Store at?0-5°C
• Sensitive: Moisture Sensitive
• BRN: 636684
• CAS DataBase Reference: 3-Methoxybenzyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxybenzyl chloride(824-98-6)
• EPA Substance Registry System: 3-Methoxybenzyl chloride(824-98-6)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 1
• F: 19-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 824-98-6(Hazardous Substances Data)

Usage

Description

3-Methoxybenzyl chloride, also known as m-anisyl chloride, is an organic compound with the chemical formula C8H9ClO2. It is a clear colorless to light yellow liquid that is soluble in organic solvents. It is an aromatic compound with a methoxy group attached to the benzene ring and a chlorine atom attached to the benzyl group. This unique structure makes it a versatile reagent in organic synthesis.

Uses

Used in Pharmaceutical Industry:
3-Methoxybenzyl chloride is used as a reagent for the synthesis of various pharmaceutical compounds. It is used in the alkylation of 8-benzyloxy-2(1H)-quinolinone in the presence of DMF and NaH, which is an important intermediate in the synthesis of certain drugs.
Used in Chemical Synthesis:
3-Methoxybenzyl chloride is used as a building block in the synthesis of various organic compounds. It is used in the synthesis of diarylmethanes via in situ organozinc-mediated, palladium-catalyzed cross-coupling between benzyl and aryl halide. This method allows for the formation of carbon-carbon bonds, which are essential in the synthesis of complex organic molecules.
Used in Organic Synthesis:
3-Methoxybenzyl chloride is used as a protecting group in organic synthesis. The methoxy group can be selectively removed under mild conditions, allowing for the controlled deprotection of the benzyl group. This makes it a useful reagent in the synthesis of complex organic molecules, where selective protection and deprotection of functional groups are necessary.

InChI:InChI=1/C8H9ClO/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,6H2,1H3

Upstream product

• 6971-51-3 3-methoxybenzyl alcohol 
• 59276-28-7 m-anisaldehyde dimethyl acetal 
• 51755-56-7 (3-methoxybenzyl)trimethylsilane 
• 1801-77-0 oxovanadium(V) ethoxydichloride 
• 1515-82-8 1-methoxy-3-(methoxymethyl)benzene 
• 100-83-4 meta-hydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 191402-51-4 5-(1-Chloro-2,2,2-trifluoro-ethyl)-2-methoxy-benzonitrile 
• 65108-13-6 C₈H₉O⁽¹⁺⁾ 
• 7782-50-5 chlorine 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 42051-04-7 3-methoxybenzyl tosylate 
• 421-50-1 1,1,1-trifluoro-2-propanone 
• 66192-25-4 2-bromo-5-methoxybenzyl chloride 

Downstream Products

• 92902-76-6 bis-(2-chloro ethyl)-(3-methoxy-benzyl)-amine 
• 20056-57-9 1-methoxy-3-pentylbenzene 
• 19924-43-7 3-methoxyphenylacetonitrile 
• 1798-09-0 m-methoxyphenylacetic acid 
• 148234-87-1 bis-(3-methoxy-benzyl)-methyl-amine 
• 36707-27-4 1,2-bis(3-methoxyphenyl)ethane 
• 55142-92-2 5-(3-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine 
• 66325-64-2 3'-methoxybenzylcyclohexanol 
• 35107-77-8 3-methoxybenzyldimethylsilane 
• 189812-98-4 [4-(3-Methoxy-phenyl)-but-1-ynyl]-trimethyl-silane 
• 65354-70-3 2-(m-Methoxyphenyl)isopropylidenecyclopropane 
• 65354-64-5 2-(m-Methoxyphenyl)-3,3-dimethylmethylenecyclopropane 
• 155820-00-1 1-methoxy-3-tert-pentylbenzene 
• 40463-03-4 2-methyl-4-(m-methoxyphenyl)-1-butene 

Relevant articles and documents

In vitro study and structure-activity relationship analysis of stilbenoid derivatives as powerful vasorelaxants: Discovery of new lead compound

The development of vasorelaxant as the antihypertensive drug is important as it produces a rapid and direct relaxation effect on the blood vessel muscles. Resveratrol (RV), as the most widely studied stilbenoid and the lead compound, inducing the excellent vasorelaxation effect through the multiple signalling pathways. In this study, the in vitro vascular response of the synthesized trans-stilbenoid derivatives, SB 1-8e were primarily evaluated by employing the phenylephrine (PE)-precontracted endothelium-intact isolated aortic rings. Herein we report trans-3,4,4′-trihydroxystilbene (SB 8b) exhibited surprisingly more than 2-fold improvement to the maximal relaxation (Rmax) of RV. This article also highlights the characterization of the aromatic protons in terms of their unique splitting patterns in 1H NMR.

Ionic-Liquid-Supported 1,3-Dimethylimidazolidin-2-one: Application as a Reusable Halogenation Reagent

We describe the synthesis of ionic-liquid-supported 1,3-dimethylimidazolidin-2-one, together with the halogenation of alcohols in a reaction system in which this reagent is combined with oxalyl chloride. A new method was established that does not require additives such as bases, and which permits the ready isolation and purification of the product. Good conversions were obtained, and good reusability of the reagent was observed.

Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols

Cinnarizine, cyclizine, buclizine, and meclizine belong to a family of antihistamines that resemble each other in terms of a 1-diphenylmethylpiperazine moiety. We present the development of a four-step continuous process to generate the final antihistamines from bulk alcohols as the starting compounds. HCl is used to synthesize the intermediate chlorides in a short reaction time and excellent yields. This methodology offers an excellent way to synthesize intermediates to be used in drug synthesis. Inline separation allows the collection of pure products and their immediate consumption in the following steps. Overall isolated yields for cinnarizine, cyclizine, and a buclizine derivative are 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1. The incredible bulk: Bulk alcohols are converted continuously into chlorides using HCl in a microflow. A reaction network that consists of four steps and two inline separations leads to the continuous preparation of cinnarizine, cyclizine, and a buclizine derivative with yields of 82, 94, and 87 %, respectively. The total residence time for the four steps is 90 min with a productivity of 2 mmol h-1.