55110-99-1

Basic information

• Product Name: 2-(4-bromophenylamino)ethan-1-ol
• Synonyms: 2-(4-bromophenylamino)ethan-1-ol
• CAS NO: 55110-99-1
• Molecular Weight: 216.077
• Mol File: 55110-99-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-(4-bromophenylamino)ethan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-bromophenylamino)ethan-1-ol(55110-99-1)
• EPA Substance Registry System: 2-(4-bromophenylamino)ethan-1-ol(55110-99-1)

Safety Data

• Hazardous Substances Data: 55110-99-1(Hazardous Substances Data)

Usage

Structure

2-(4-bromophenylamino)ethan-1-ol, N-(4-bromophenyl)-2-hydroxyethylamine

Classification

Primary amine, alcohol

Physical appearance

Off-white to light brown powder

Molecular weight

214.07 g/mol

Uses

Synthesis of pharmaceuticals and organic compounds, reagent in organic chemistry for various reactions (e.g. formation of amides, esters, and other functional groups)

Versatility

Presence of bromine and amino group makes it a building block for the synthesis of complex organic molecules.

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 106-40-1 4-bromo-aniline 
• 915712-34-4 (4-bromo-phenylimino)-acetic acid ethyl ester 
• 589-87-7 1,4-bromoiodobenzene 
• 141-43-5 ethanolamine 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 75-21-8 oxirane 

Downstream Products

• 223555-95-1 3?(4?bromophenyl)oxazolidin?2?one 
• 1219725-81-1 1-(4-(1H-pyrazol-4-yl)phenyl)-1-(2-hydroxyethyl)-3-(3-methoxybenzyl)urea 
• 774604-41-0 (4-bromo-phenyl)-(2-hydroxy-ethyl)-carbamic acid benzyl ester 
• 80077-18-5 N-[3-(4-Bromo-phenyl)-[1,3,2]oxazaphospholidin-2-yl]-N',N'-dimethyl-benzene-1,4-diamine 
• 1606589-19-8 C₁₇H₂₆BrNO₂Si 
• 1338326-88-7 4-bromo-N-[2-[tert-butyl(dimethyl)silyl]oxyethyl]aniline 
• 1606589-30-3 C₁₁H₁₂BrNO₂ 
• 1606589-42-7 C₁₁H₁₀BrNO₂ 
• 1606589-54-1 1-(4-bromophenyl)-4-hydroxy-3-methylenepyrrolidin-2-one 
• 80077-22-1 3-(4-Bromo-phenyl)-2-chloro-[1,3,2]oxazaphospholidine 

Relevant articles and documents

Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides

An efficient and highly practical procedure is reported for the Ullmann-Goldberg-type copper-catalyzed amination of aryl iodides. By using a combination of copper iodide and proline in the presence of an excess of an amine, a wide range of aryl iodides can be readily aminated at room temperature. The reaction proceeds well regardless of the electronic properties of the starting aryl iodide and the amination products can be obtained without the need for purification by column chromatography in most cases. Owing to its efficiency and the mildness of the reaction conditions, this amination could also be extended to the amination of complex aryl iodides at room temperature.

BmimOAc ionic liquid: A highly efficient catalyst for synthesis of 3-aryl-2-oxazolidinones by direct condensation of 2-(arylamino) alcohols with diethyl carbonate

An efficient convenient procedure for the synthesis of 3-aryl-2-oxazolidinones from 2-(arylamino) alcohols and diethyl carbonate (DEC) catalyzed by ionic liquids is described. The effects of reaction time, amount of catalyst and temperature were investigated. Excellent yields of products were obtained under the optimized reaction conditions, when using BmimOAc as a catalyst. An intermediate ethyl 2-(phenyl amino) ethyl carbonate was isolated and characterized. 1H NMR spectroscopy and DFT calculations indicated that BmimOAc cooperatively activate the substrates through hydrogen bonding with its anion and cation sites. According to these results, a possible reaction mechanism was discussed.

Synthesis and biological evaluation of urea derivatives as highly potent and selective rho kinase inhibitors

RhoA and its downstream effector ROCK mediate stress fiber formation and cell contraction through their effects on the phosphorylation of myosin light chain (MLC). Inhibition of the RhoA/ROCK pathway has proven to be a promising strategy for several indications such as cardiovascular disease, glaucoma, and inflammatory disease. In 2010, our group reported urea-based ROCK inhibitors as potential antiglaucoma agents. These compounds showed potent IC50 values in enzymatic and cell-based assays and significant intraocular pressure (IOP)-lowering effects in rats (～7 mmHg).(22) To develop more advanced ROCK inhibitors targeting various potential applications (such as myocardial infarction, erectile dysfunction, multiple sclerosis, etc.) in addition to glaucoma, a thorough SAR for this urea-based scaffold was studied. The detailed optimization process, counter-screening, and in vitro and in vivo DMPK studies are discussed. Potent and selective ROCK inhibitors with various in vivo pharmacokinetic properties were discovered.