3-(Bromomethyl)-1,2,4,5-tetramethoxybenzene

Base Information

• Chemical Name: 3-(Bromomethyl)-1,2,4,5-tetramethoxybenzene
• CAS No.: 86489-89-6
• Molecular Formula: C11H15BrO4
• Molecular Weight: 291.142
• DSSTox Substance ID: DTXSID40441195
• Nikkaji Number: J1.278.149K
• Wikidata: Q82257846
• Mol file: 86489-89-6.mol

Synonyms:3-(BROMOMETHYL)-1,2,4,5-TETRAMETHOXYBENZENE;86489-89-6;DTXSID40441195;AMY15147;2,3,5,6-Tetramethoxybenzyl bromide;FD7116;A846941

Chemical Property of 3-(Bromomethyl)-1,2,4,5-tetramethoxybenzene

Chemical Property:

• Melting Point: 127℃
• Boiling Point: 340.937 °C at 760 mmHg
• Flash Point: 138.631 °C
• PSA: 36.92000
• Density: 1.355 g/cm³
• LogP: 2.61590
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 290.01537
• Heavy Atom Count: 16
• Complexity: 184

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C(=C1OC)CBr)OC)OC

Technology Process of 3-(Bromomethyl)-1,2,4,5-tetramethoxybenzene

There total 12 articles about 3-(Bromomethyl)-1,2,4,5-tetramethoxybenzene 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: 87.0%

(2,3,5,6-tetramethoxyphenyl)methanol (181819-59-0) → 3-(bromomethyl)-1,2,4,5-tetramethoxybenzene (86489-89-6)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at -7 ℃;

DOI:10.1021/jo9805192

Reference yield: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,2,4,5-tetramethoxybenzene (2441-46-5) → 3-(bromomethyl)-1,2,4,5-tetramethoxybenzene (86489-89-6)

Guidance literature:

With hydrogen bromide;

DOI:10.1002/(SICI)1521-3773(19991216)38:24<3710::AID-ANIE3710>3.0.CO;2-H

Reference yield: 16.0%

bromethyl methyl ether (13057-17-5) + 1,2,4,5-tetramethoxybenzene (2441-46-5) → 3-(bromomethyl)-1,2,4,5-tetramethoxybenzene (86489-89-6) + 1,4-bis(bromomethyl)-2,3,5,6-tetramethoxybenzene (86489-87-4)

Guidance literature:

In trifluoroacetic acid; for 22h; Ambient temperature; excess of bromomethyl methyl ether;

DOI:10.1016/S0040-4020(01)91854-X

upstream raw materials:

bromethyl methyl ether

1,2,4,5-tetramethoxybenzene

(2,3,5,6-tetramethoxyphenyl)methanol

formaldehyd

Downstream raw materials:

2,3,5,6-tetramethoxybenzaldehyde

ilimaquinone

[1R-(1α,2β,4aβ,8aα)]-3-[(decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl]-2,5-dimethoxy-2,5-cyclohexadiene-1,4-dione

[1R-(1β,2β,4aβ,8aα)]-3-(1,2,3,4,4a,7,8,8a-octahydro-1,2,4a,5-tetramethyl-1-naphthyl)methyl-2-hydroxy-5-methoxy-2,5-cyclohexadiene-1,4-dione

Refernces

• 1、 Filosa, Rosanna,Peduto, Antonella,Aparoy, Polamarasetty,Schaible, Anja M.,Luderer, Susann,Krauth, Verena,Petronzi, Carmen,Massa, Antonio,De Rosa, Mario,Reddanna, Pallu,Werz, Oliver. "Discovery and biological evaluation of novel 1,4-benzoquinone and related resorcinol derivatives that inhibit 5-lipoxygenase". . p. 269 - 279. Retrieved 2013/10/01.
• 2、 Stahl, Petra,Waldmann, Herbert. "Asymmetric synthesis of the nakijiquinones - Selective inhibitors of the Her-2/Neu protooncogene". . p. 3710 - 3713. Retrieved 2007/10/03.