4-Bromo-N-ethyl-N-methylaniline

Base Information

• Chemical Name: 4-Bromo-N-ethyl-N-methylaniline
• CAS No.: 67274-54-8
• Molecular Formula: C9H12BrN
• Molecular Weight: 214.105
• DSSTox Substance ID: DTXSID90518861
• Wikidata: Q82381704
• Mol file: 67274-54-8.mol

Synonyms:4-Bromo-N-ethyl-N-methylaniline;67274-54-8;SCHEMBL1433223;N-ethyl-4-bromo-N-methylaniline;DTXSID90518861;DBMDDFTYMKZYTR-UHFFFAOYSA-N

Chemical Property of 4-Bromo-N-ethyl-N-methylaniline

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 213.01531
• Heavy Atom Count: 11
• Complexity: 108

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(C)C1=CC=C(C=C1)Br

Technology Process of 4-Bromo-N-ethyl-N-methylaniline

There total 10 articles about 4-Bromo-N-ethyl-N-methylaniline 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: 99.0%

N-(4-bromo-phenyl)-N-methylacetamide (50438-47-6) → 4-bromo-N-methyl-N-ethylaniline (67274-54-8)

Guidance literature:

With Triethoxysilane; sodium triethylborohydride; In hexane; at 80 ℃; for 6h; Schlenk technique; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1021/acs.joc.9b02211

Reference yield: 99.0%

N-(4-bromo-phenyl)-N-methylacetamide (50438-47-6) → 4-bromo-N-methylaniline (6911-87-1,211060-12-7) + 4-bromo-N-methyl-N-ethylaniline (67274-54-8)

Guidance literature:

With triethyl borane; Triethoxysilane; sodium hydroxide; In hexane; at 80 ℃; for 6h; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;

Reference yield: 69.0%

N-Ethylmethylamine (624-78-2) + 1,4-bromoiodobenzene (589-87-7) → 4-bromo-N-methyl-N-ethylaniline (67274-54-8)

Guidance literature:

With potassium phosphate; copper(ll) bromide; 1,1'-bi-2-naphthol; In N,N-dimethyl-formamide; at 70 ℃; for 48h;

upstream raw materials:

N-methyl-N-ethylaniline

N-ethyl-N-(4-bromo-phenyl)-glycine nitrile

(4-Bromo-phenyl)-ethyl-methyl-amine; compound with bromine

sulfuric acid

Downstream raw materials:

(4-Bromo-phenyl)-ethyl-methyl-amine; compound with bromine

Refernces

• 1、 Yao, Wubing,He, Lili,Han, Deman,Zhong, Aiguo. "Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines". . p. 14627 - 14635. Retrieved 2019/12/02.
• 2、 Pan, Yixiao,Luo, Zhenli,Han, Jiahong,Xu, Xin,Chen, Changjun,Zhao, Haoqiang,Xu, Lijin,Fan, Qinghua,Xiao, Jianliang. "B(C6F5)3-Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane". supporting information. p. 2301 - 2308. Retrieved 2019/01/30.