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

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

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

Downstream Products

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

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.

N-Arylazetidines: Preparation through Anionic Ring Closure

We report herein an efficient synthesis of diversely substituted N-aryl-2-cyanoazetidines based on an anionic ring-closure reaction. These compounds can be prepared from β-amino alcohols in enantiomerically pure form through a three-step sequence involving (i) copper-catalyzed N-arylation, (ii) N-cyanomethylation of the secondary aniline, and (iii) one-pot mesylation followed by ring closure induced by a base. This high-yielding sequence gives access to azetidines with a predictable and adjustable substitution pattern and also with predictable diastereoselectivity. These compounds are susceptible to multiple further derivatizations through Suzuki coupling or nitrile transformation, thus appearing as valuable new scaffolds for medicinal chemistry. Their rigid shape, featuring an almost planar N-arylamine and a planar four-membered ring, was revealed by both AM1 calculations and X-ray crystallography.

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.

Highly Efficient Mechanochemical N-Arylation of Amino Alcohols and Diamines with Cu0 Powder

Cu0-catalysed arylations have rightly acquired great importance over the last decade. This paper reports the N-arylation of amino alcohols and diamines with iodobenzene derivatives in a planetary ball mill and an investigation into the procedure. This newly developed solvent-free protocol is fast, efficient and occurs under the mechanochemical activation of metallic copper powder. It does not require additional ligands and gives excellent yields. This paper aims to broaden the scope of mechanochemical Cu0-activation and so a new one-pot, two-step synthesis that combines CuAAC and N-arylation has been successfully performed and reported herein.

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.

Substrate-promoted copper-catalyzed N-arylation of amino alcohols with aryl iodides in water

An efficient method has been developed for the N-arylation of a variety of water-soluble amino alcohols (1.2 mmol) with aryl iodides (1.0 mmol) in water under CuI-catalyzed conditions. The reaction was conducted via substrate-promoted action and did not require an additional ligand or phase-transfer catalyst, and afforded the desired N-aryl amines in acceptable to excellent yields (64%-93%) under mild reaction conditions with a small excess of the amino alcohol.

Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides

A simple and mild method for the coupling of aryl halides with amino alcohols and diamines is described. The reactions can be performed under ligand-free and solvent-free conditions, and generate the products in good yield.

A new one-pot, four-component synthesis of 1,2-amino alcohols: TiCl 3/t-BuOOH-mediated radical hydroxymethylation of imines

(Chemical Equation Presented) An amine, an aldehyde, and methanol can be readily assembled in one pot under very mild conditions through a free-radical multicomponent reaction by using an aqueous acidic TiCl3/t-BuOOH system to afford 1,2-amino alcohols in fair to excellent yields.