4-Bromoveratrole

Base Information

• Chemical Name: 4-Bromoveratrole
• CAS No.: 2859-78-1
• Molecular Formula: C8H9BrO2
• Molecular Weight: 217.062
• Hs Code.: 29093038
• European Community (EC) Number: 220-677-8
• NSC Number: 36284
• UNII: 9GX67R5G8J
• DSSTox Substance ID: DTXSID1062673
• Nikkaji Number: J150.890C
• Wikidata: Q72513692
• Mol file: 2859-78-1.mol

Synonyms:4-Bromoveratrole;2859-78-1;4-Bromo-1,2-dimethoxybenzene;1-Bromo-3,4-dimethoxybenzene;3,4-Dimethoxybromobenzene;Benzene, 4-bromo-1,2-dimethoxy-;p-Bromoveratrole;3,4-Dimethoxyphenyl bromide;MFCD00008381;4-bromo-1,2-dimethoxy-benzene;9GX67R5G8J;4-bromanyl-1,2-dimethoxy-benzene;EINECS 220-677-8;NSC 36284;NSC-36284;AI3-21224;1,2-dimethoxy-4-bromobenzene;4-bromoveratrol;4-Bromocatechol Dimethyl Ether;4-Bromoveratrole, 98%;3,4-dimethoxybromo-benzene;UNII-9GX67R5G8J;SCHEMBL20509;4-Bromoguaiacol, methyl ether;DTXSID1062673;KBTMGSMZIKLAHN-UHFFFAOYSA-;NSC36284;AKOS000178813;AM61447;CS-W007396;AS-13440;SY004442;A5409;B1021;FT-0617929;EN300-35674;J-514847;W-107038;Z57462741;IS0

Chemical Property of 4-Bromoveratrole

Chemical Property:

• Appearance/Colour: colorless or light yellow transparent liquid
• Vapor Pressure: 0.113mmHg at 25°C
• Refractive Index: n20/D 1.573(lit.)
• Boiling Point: 255.5 °C at 760 mmHg
• Flash Point: 109 °C
• PSA: 18.46000
• Density: 1.412 g/cm³
• LogP: 2.46630
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in benzene, ether, toluene.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 215.97859
• Heavy Atom Count: 11
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

4-Bromo-1,2-dimethoxybenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)Br)OC
• Uses: 4-Bromoveratrole is a metabolite of bromobenzene, with a catechol moiety in the substructure. It also has use as a redox shuttle additive, essentially a component in lithium batteries that consumes excess current during overcharge. It is also used in the synthesis of the isoquinoline alkaloid (-)-mesembrine.
• Biological Functions: 4-Bromoveratrole has been shown that this molecule binds to the receptor for acetylcholine, which is found in the central nervous system and on muscles. The binding of 4-bromoveratrole to this receptor leads to the release of chloride ions from the cell, which increases the activity of acetylcholine. The detection sensitivity of 4-bromoveratrole in solution was determined by adding malonic acid or hydrochloric acid, which led to an increase in fluorescence intensity. This molecule also has fatty acid and hydroxyl groups that have been shown to have anti-inflammatory properties.

Technology Process of 4-Bromoveratrole

There total 16 articles about 4-Bromoveratrole 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: 100.0%

1,2-dimethoxybenzene (91-16-7) → 4-Bromoveratrole (2859-78-1)

Guidance literature:

With kaolin; sodium chlorite; manganese(III) acetylacetonate; sodium bromide; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1039/a804043e

Reference yield: 95.0%

2-bromo-4,5-dimethoxybenzoic acid (6286-46-0) → 4-Bromoveratrole (2859-78-1)

Guidance literature:

With silver(I) acetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 16h; Inert atmosphere;

DOI:10.1039/b912509d

Reference yield: 93.0%

1,2-dimethoxybenzene (91-16-7) → 1,2-dibromo-4,5-dimethoxybenzene (37895-73-1) + 4-Bromoveratrole (2859-78-1)

Guidance literature:

With oxygen; 1,1-dibromomethane; at 50 ℃; for 1h;

DOI:10.1002/asia.201200322

upstream raw materials:

1,2-dimethoxybenzene

bromocyane

pyridinium hydrobromide perbromide

1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione

Downstream raw materials:

2-(3,4-dimethoxyphenyl)ethyl alcohol

1,2-dimethoxy-4-phenoxybenzene

1,2-dimethoxy-4-(2-methoxy-phenoxy)-benzene

1-bromo-4,5-dimethoxy-2-nitro-benzene

Refernces

• 1、 Fedorova,Koshkin,Gromov,Avakyan,Nazarov,Brichkin,Vershinnikova,Nikolaeva,Chernych,Alfimov. "Crown-containing spironaphthoxazines and spiropyrans 3. Synthesis and investigation of the merocyanine form of crown-containing spirobenzothiazolinonaphthoxazine". . p. 1441 - 1450. Retrieved 2002.
• 2、 He, Xinxin,Wang, Xinyan,Tse, Ying-Lung Steve,Ke, Zhihai,Yeung, Ying-Yeung. "Bis-selenonium Cations as Bidentate Chalcogen Bond Donors in Catalysis". . p. 12632 - 12642. Retrieved 2021/10/21.
• 3、 Richards, Kenza,Petit, Eddy,Legrand, Yves-Marie,Grison, Claude. "Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids". supporting information. p. 809 - 814. Retrieved 2020/11/30.