16532-79-9

Usage

Uses

Used in Pharmaceutical Research:
4-Bromophenylacetonitrile is used as a chemical model for the study and analysis of human buccal absorption of pharmaceuticals. This application helps researchers understand the absorption process and develop more effective drug delivery systems.
Used in Polymer Synthesis:
In the field of polymer chemistry, 4-Bromophenylacetonitrile is used in the synthesis of new fluorene-based alternating polymers and light-emitting copolymers, such as poly(N 4,N 4-bis-(4-phenyl)-N 4,N 4′-bis-[4-(2-ethylhexyloxy)phenyl]-biphenyl-4,4′-diamine-co-1,2-bis(4′-phenyl)-1-(9′′,9′′-dihexyl-3-fluorenyl)ethane). These materials have potential applications in the development of organic light-emitting diode (OLED) technology.
Used in OLED Material Synthesis:
4-Bromophenylacetonitrile is also used in the synthesis of N-methyl-3,4-bis(4-(N-(1-naphthyl)phenylamino)phenyl)maleimide, a novel non-doped red organic light-emitting diode (OLED) material. This material contributes to the advancement of OLED technology and its applications in display and lighting industries.

Safety Profile

Poison by intravenous route. See also BROMIDES and NITRILES. When heated to decomposition it emits very toxic fumes of Br-, NOx, and CN-.

InChI:InChI=1/C8H6BrN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 106-49-0 p-toluidine 
• 151-50-8 potassium cyanide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 106-38-7 para-bromotoluene 
• 143-33-9 sodium cyanide 
• 589-17-3 p-bromobenzyl chloride 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 55883-45-9 4-bromobenzyliodide 
• 501325-59-3 1-((allylsulfonyl)methyl)-4-bromobenzene 
• 2942-58-7 diethyl cyanophosphonate 
• 100-44-7 benzyl chloride 
• 773837-37-9 sodium cyanide 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 

Downstream Products

• 96463-58-0 2-(4-bromo-phenyl)-3c-(5-bromo-[2]thienyl)-acrylonitrile 
• 102661-91-6 4-(4-bromo-benzyl)-quinoline 
• 107413-80-9 2-(4-bromo-phenyl)-3c-(4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-acrylonitrile 
• 14062-25-0 Ethyl 4-bromophenylacetate 
• 115080-37-0 2-(4-bromo-phenyl)-3-(4-isopropyl-phenyl)-3-phenyl-acrylonitrile 
• 74860-13-2 4-bromobenzeneacetamide 
• 6186-21-6 α-acetyl-α-(p-bromophenyl)acetonitrile 
• 73918-56-6 4-Bromophenethylamine 
• 82193-93-9 (2E)-2,3-bis(4-bromophenyl)-2-butenedinitrile 
• 147111-30-6 2-(4-bromophenyl)ethanethioamide 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 133132-70-4 (Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl) acrylonitrile 
• 102027-28-1 2,2-bis-[2-(4-bromo-phenyl)-acetylamino]-1,1,1-trichloro-ethane 

Relevant academic research and scientific papers

Radical trifunctionalization of hexenenitrile via remote cyano migration

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Photobleaching Efficiency Parallels the Enhancement of Membrane Damage for Porphyrazine Photosensitizers

Photostability is considered a key asset for photosensitizers (PS) used in medical applications as well as for those used in energy conversion devices. In light-mediated medical treatments, which are based on PS-induced harm to diseased tissues, the photoinduced cycle of singlet oxygen generation has always been considered to correlate with PS efficiency. However, recent evidence points to the fundamental role of contact-dependent reactions, which usually cause PS photobleaching. Therefore, it seems reasonable to challenge the paradigm of photostability versus PS efficiency in medical applications. We have prepared a series of Mg(II) porphyrazines (MgPzs) having similar singlet oxygen quantum yields and side groups with different electron-withdrawing strengths that fine-tune their redox properties. A detailed investigation of the photobleaching mechanism of these porphyrazines revealed that it is independent of singlet oxygen, occurring mainly via photoinduced electron abstraction of surrounding electron rich molecules (solvents or lipids), as revealed by the formation of an air-stable radical anion intermediate. When incorporated into phospholipid membranes, photobleaching of MgPzs correlates with the degree of lipid unsaturation, indicating that it is caused by an electron abstraction from the lipid double bond. Interestingly, upon comparing the efficiency of membrane photodamage between two of these MgPzs (with the highest and the lowest photobleaching efficiencies), we found that the higher the rate of PS photobleaching the faster the leakage induced in the membranes. Our results therefore indicate that photobleaching is a necessary step toward inflicting irreversible biological damage. We propose that the design of more efficient PS for medical applications should contemplate contact-dependent reactions as well as strategies for PS regeneration.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Design and synthesis of a magnetic hierarchical porous organic polymer: A new platform in heterogeneous phase-transfer catalysis

Recyclable phase transfer catalysts containing magnetic nanoparticles (MNPs) have been known as a major trend towards sustainable catalysts. In this study, a novel class of magnetic porous polymer on the basis of calix[4]resorcinarene was synthesized starting from silica-coated Fe3O4 core-shell nanoparticles. This compound was found as an efficient phase transfer catalyst to the conversion of benzyl halides into benzyl azides and cyanides in good yields. The catalyst could be used at least for five consecutive cycles without appreciable loss in the catalytic activity.

Crown ether functionalized magnetic hydroxyapatite as eco-friendly microvessel inorganic-organic hybrid nanocatalyst in nucleophilic substitution reactions: an approach to benzyl thiocyanate, cyanide, azide and acetate derivatives

In this paper, high catalytic activity of 4′,4″-diformyl dibenzo-18-crown-6 anchored onto the functionalized magnetite hydroxyapatite (γ-Fe2O3@HAp–Crown) as a new, versatile and magnetically recoverable catalyst, was prepared. It evaluated as phase-transfer catalyst and molecular host system for nucleophilic substitution reactions of benzyl halides with thiocyanate, cyanide, azide and acetate anions in water. No evidence for the formation of by-products was observed and the products obtained in pure form without further purification. The nanocomposite was easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The synthesized nanocomposite was characterized by several techniques such as FT-IR, TGA-DTG, EDX, XRD, BET, FE-SEM, TEM and VSM.

HEPATITIS C VIRUS INHIBITORS AND USES THEREOF IN PREPARATION OF DRUGS

A series of hepatitis C virus (HCV) inhibitors and compositions and applications thereof in the preparation of drugs for treating chronic HCV infection. Especially, a series of compounds that are used as NS5A inhibitors, and compositions and uses thereof in the preparations of drugs.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.