3,5-Dimethoxybenzyl chloride

Base Information

• Chemical Name: 3,5-Dimethoxybenzyl chloride
• CAS No.: 6652-32-0
• Molecular Formula: C9H11ClO2
• Molecular Weight: 186.638
• Hs Code.: 2909309090
• European Community (EC) Number: 624-645-8
• DSSTox Substance ID: DTXSID50374304
• Nikkaji Number: J1.035.406D
• Wikidata: Q72467745
• Mol file: 6652-32-0.mol

Synonyms:3,5-Dimethoxybenzyl chloride;6652-32-0;1-(Chloromethyl)-3,5-dimethoxybenzene;MFCD00074902;Benzene, 1-(chloromethyl)-3,5-dimethoxy-;3,5-Dimethoxybenzylchloride;3,5-dimethoxy benzylchloride;3,5-dimethoxy-benzylchloride;3,5-dimethoxy benzyl chloride;3,5-dimethoxy- benzylchloride;SCHEMBL1279836;DTXSID50374304;CCAWDIFJOBKBSE-UHFFFAOYSA-N;1-Chloromethyl-3,5-dimethoxybenzene;3,5-Dimethoxybenzyl chloride, 99%;STL279749;AKOS000261560;AB02846;1-(chloromethyl)-3,5-dimethoxy-benzene;AC-16564;AS-30498;FT-0636226;A835482;AN-651/40724474;F2190-0275

Chemical Property of 3,5-Dimethoxybenzyl chloride

Chemical Property:

• Melting Point: 46-48 °C
• Refractive Index: 1.5230 (estimate)
• Boiling Point: 334.1 °C at 760 mmHg
• Flash Point: 113.5 °C
• PSA: 18.46000
• Density: 1.13 g/cm³
• LogP: 2.44260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 186.0447573
• Heavy Atom Count: 12
• Complexity: 118

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,5-Dimethoxybenzyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1)CCl)OC
• 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.

Technology Process of 3,5-Dimethoxybenzyl chloride

There total 7 articles about 3,5-Dimethoxybenzyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3,5-dimethoxybenzyl alcohol (705-76-0) → 3,5-dimethoxybenzylchloride (6652-32-0)

Guidance literature:

With pyridine; thionyl chloride; In diethyl ether; at 20 ℃; Cooling with ice;

DOI:10.1016/j.tetlet.2012.04.132

Reference yield: 95.0%

methyl 3,5-dimethoxybenzoate (2150-37-0) → 3,5-dimethoxybenzylchloride (6652-32-0)

Guidance literature:

methyl 3,5-dimethoxybenzoate; With lithium aluminium tetrahydride; In tetrahydrofuran;

With thionyl chloride; In tetrahydrofuran; diethyl ether;

DOI:10.1002/cjoc.201180279

Reference yield:

3,5-dimethoxybenzaldehdye (7311-34-4) → 3,5-dimethoxybenzylchloride (6652-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / BH₃*THF / tetrahydrofuran / 12 h

2: 70 percent / methanesulfonyl chloride; triethylamine

With borane-THF; methanesulfonyl chloride; triethylamine; In tetrahydrofuran;

DOI:10.1021/ja0499389

upstream raw materials:

3,5-dimethoxybenzyl alcohol

methyl 3,5-dimethoxybenzoate

3,5-dimethoxybenzaldehdye

3,5-dimethoxybenzoic acid

Downstream raw materials:

1-(iodomethyl)-3,5-dimethoxybenzene

1-(3,5-dimethoxyphenyl)-2-hydroxytridecane

2-(3,5-dimethoxyphenyl)-1-(4'-methyoxyphenyl)ethan-1-ol

1-(3,4-dimethoxyphenyl)-2-(3',5'-dimethoxyphenyl)ethan-1-ol

Refernces

• 1、 Ho?ek, Jan,Leláková, Veronika,Bobál, Pavel,Pí?ová, Hana,Gazdová, Markéta,Malaník, Milan,Jakubczyk, Karolina,Vesely, Ond?ej,Landa, P?emysl,Temml, Veronika,Schuster, Daniela,Prachyawarakorn, Vilailak,Pailee, Phanruethai,Ren, Gang,Zpurny, Filip,Oravec, Michal,?mejkal, Karel. "Prenylated Stilbenoids Affect Inflammation by Inhibiting the NF-κB/AP-1 Signaling Pathway and Cyclooxygenases and Lipoxygenase". . p. 1839 - 1848. Retrieved 2019/08/20.
• 2、 Semenova, Marina N.,Demchuk, Dmitry V.,Tsyganov, Dmitry V.,Chernysheva, Natalia B.,Samet, Alexander V.,Silyanova, Eugenia A.,Kislyi, Victor P.,Maksimenko, Anna S.,Varakutin, Alexander E.,Konyushkin, Leonid D.,Raihstat, Mikhail M.,Kiselyov, Alex S.,Semenov, Victor V.. "Sea Urchin Embryo Model As a Reliable in Vivo Phenotypic Screen to Characterize Selective Antimitotic Molecules. Comparative evaluation of Combretapyrazoles, -isoxazoles, -1,2,3-triazoles, and -pyrroles as Tubulin-Binding Agents". . p. 700 - 721. Retrieved 2019/01/03.