2-Bromo-4,5-dimethoxybenzylamine

Base Information

• Chemical Name: 2-Bromo-4,5-dimethoxybenzylamine
• CAS No.: 89525-51-9
• Molecular Formula: C9H12 Br N O2
• Molecular Weight: 246.104
• ChEMBL ID: CHEMBL4590727
• DSSTox Substance ID: DTXSID50528365
• Nikkaji Number: J2.947.564D
• Wikidata: Q82397935
• Mol file: 89525-51-9.mol

Synonyms:2-BROMO-4,5-DIMETHOXYBENZYLAMINE;89525-51-9;(2-Bromo-4,5-dimethoxyphenyl)methanamine;CHEMBL4590727;DTXSID50528365;AKOS009132610;1-(2-Bromo-4,5-dimethoxyphenyl)methanamine;EN300-145897

Chemical Property of 2-Bromo-4,5-dimethoxybenzylamine

Chemical Property:

• PSA: 44.48000
• LogP: 2.62530
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.00514
• Heavy Atom Count: 13
• Complexity: 157

Purity/Quality:

99%min ^*data from raw suppliers

2-BROMO-4,5-DIMETHOXYBENZYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)CN)Br)OC

Technology Process of 2-Bromo-4,5-dimethoxybenzylamine

There total 6 articles about 2-Bromo-4,5-dimethoxybenzylamine 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: 93.0%

2-bromo-4,5-dimethoxybenzaldehyde (5392-10-9) → (2-bromo-4,5-dimethoxyphenyl)methanamine (89525-51-9)

Guidance literature:

2-bromo-4,5-dimethoxybenzaldehyde; With tert-butyldimethylsilane; methyl carbamate; trifluoroacetic acid; In acetonitrile; at 80 ℃; for 6h;

With water; lithium hydroxide; In tetrahydrofuran; methanol; at 80 ℃; for 16h;

DOI:10.1016/j.tet.2011.12.060

Reference yield: 83.0%

2-bromo-4,5-dimethoxybenzaldehyde oxime (198204-67-0) → (2-bromo-4,5-dimethoxyphenyl)methanamine (89525-51-9)

Guidance literature:

With hydrogenchloride; zinc; In tetrahydrofuran; water; Reflux;

DOI:10.3987/COM-13-S(S)62

Reference yield:

2-bromo-4,5-dimethoxybenzyl alcohol (54370-00-2) → (2-bromo-4,5-dimethoxyphenyl)methanamine (89525-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; phosphorus tribromide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: ammonia / ethanol; water / 4 h / 20 °C

With pyridine; ammonia; phosphorus tribromide; In ethanol; dichloromethane; water;

DOI:10.1021/ol403365

upstream raw materials:

2-bromo-4,5-dimethoxybenzaldehyde oxime

2-bromo-4,5-dimethoxybenzaldehyde

3,4-dimethoxy-benzaldehyde

2-bromo-4,5-dimethoxybenzyl alcohol

Downstream raw materials:

1-(2-bromo-4,5-dimethoxybenzyl)-5-(4-methylbenzyl)-3,4-dihydropyridin-2(1H)-one

8,9-dimethoxy-1-(4-methylbenzyl)-2,6-dihydropyrido[2,1-a]isoindol-4(3H)-one

N-(2-bromo-4,5-dimethoxybenzyl)-4-methylbenzenesulfonamide

2,3-dimethoxy-6-tosyl-5,6-dihydroindolo[1,2-a]quinazoline

Refernces

• 1、 Sato, Manabu,Azuma, Hiroki,Daigaku, Akihiro,Sato, Sota,Takasu, Kiyosei,Okano, Kentaro,Tokuyama, Hidetoshi. "Total Synthesis of (?)-Histrionicotoxin through a Stereoselective Radical Translocation–Cyclization Reaction". supporting information. p. 1087 - 1091. Retrieved 2017/01/18.
• 2、 Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai. "CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines". . p. 484 - 487. Retrieved 2014/04/03.