4-Bromo-2,N,N-trimethylaniline

Base Information

• Chemical Name: 4-Bromo-2,N,N-trimethylaniline
• CAS No.: 50638-49-8
• Molecular Formula: C9H12BrN
• Molecular Weight: 214.105
• Hs Code.: 2921430090
• DSSTox Substance ID: DTXSID20466144
• Nikkaji Number: J1.625.193C
• Wikidata: Q82292627
• Mol file: 50638-49-8.mol

Synonyms:4-Bromo-N,N,2-trimethylaniline;4-BROMO-2,N,N-TRIMETHYLANILINE;50638-49-8;p-Brom-dimethyl-o-toluidin;SCHEMBL14808309;DTXSID20466144;4-bromanyl-N,N,2-trimethyl-aniline;MFCD07368223;AKOS016008631;AB31930;Benzenamine, 4-bromo-N,N,2-trimethyl-;BS-28618;CS-0205490;A828214

Chemical Property of 4-Bromo-2,N,N-trimethylaniline

Chemical Property:

• PSA: 3.24000
• LogP: 2.82350
• Storage Temp.: 2-8°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 213.01531
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

99%, ^*data from raw suppliers

4-Bromo-2,N,N-trimethylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)Br)N(C)C

Technology Process of 4-Bromo-2,N,N-trimethylaniline

There total 16 articles about 4-Bromo-2,N,N-trimethylaniline 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: 92.0%

N,N-dimethyl-o-toluidine (609-72-3) → 2-methyl-4-bromo-N,N-dimethylaniline (50638-49-8)

Guidance literature:

With N-Bromosuccinimide; ammonium acetate; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1039/c6cc04531f

Reference yield: 92.0%

2,4-dibromo-N,N-dimethylaniline (64230-27-9) + methyl iodide (74-88-4) → 2-methyl-4-bromo-N,N-dimethylaniline (50638-49-8)

Guidance literature:

With methyllithium; In various solvent(s); at 20 ℃;

DOI:10.1081/SCC-100104832

Reference yield: 51.0%

N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide (6852-47-7) → 2-methyl-4-bromo-N,N-dimethylaniline (50638-49-8)

Guidance literature:

N,N-dimethyl-N-(2'-methylphenyl)amine N-oxide; With sulfurous dibromide; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

With triethylamine; In tetrahydrofuran; at -78 - 23 ℃; for 0.75h; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.8b01590

upstream raw materials:

formaldehyd

2,4-dibromo-6-methylaniline

chloroform

N,N-dimethyl-o-toluidine

Downstream raw materials:

(4,5-Dibromo-2-methyl-phenyl)-dimethyl-amine

N⁴,N⁴,N^4',N^4',3,3'-hexamethyl-[1,1'-biphenyl]-4,4'-diamine

bis(n-butylsulfenyl)(N,N-dimethylamino)methylbenzene

N,N,2-trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Refernces

• 1、 -. "Novel monoacylglycerol lipase inhibitor as well as preparation method and application thereof". Paragraph 0239-0241. . Retrieved 2021/02/10.
• 2、 Yi, Yuan-Qiu-Qiang,Yang, Wen-Cheng,Zhai, Dan-Dan,Zhang, Xiang-Yu,Li, Shuai-Qi,Guan, Bing-Tao. "Nickel-catalyzed C-N bond reduction of aromatic and benzylic quaternary ammonium triflates". supporting information. p. 10894 - 10897. Retrieved 2016/09/09.