5798-79-8

Usage

Uses

Used in Riot Control and War Gas:
Bromobenzyl cyanide is used as a tear gas in riot control situations to disperse crowds and maintain public order. Its irritating properties make it effective for this application, causing temporary discomfort and disorientation when inhaled or when it comes into contact with the eyes.
Used in Agricultural Fungicides:
In the agricultural industry, Bromobenzyl cyanide is used as a fungicide to control certain fungal diseases of stone fruit, such as peaches, plums, and cherries. Its chemical properties allow it to effectively target and eliminate fungi that can damage or destroy crops, ensuring a healthy and productive harvest.

Production Methods

The preparation of bromophenylacetonitrile consists of three steps: chlorination of toluene to form benzyl chloride, (2) conversion of benzyl chloride to benzyl cyanide by action of sodium cyanide in alcoholic solution, and bromination of benzyl cyanide with bromide vapor in the presence of sunlight.

Hazard

Toxic, lacrimator.

Safety Profile

Poison by ingestion. Moderately toxic to humans by inhalation. When heated to decomposition it emits very toxic fumes of NOx, Br-, and CN-. See also NITRILES.

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

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 6362-63-6 ethyl 3-cyano-3-phenylpyruvate 
• 532-28-5 (RS)-mandelonitrile 
• 128-08-5 N-Bromosuccinimide 
• 140-29-4 phenylacetonitrile 
• 506-68-3 bromocyane 
• 141-52-6 sodium ethanolate 

Downstream Products

• 92042-94-9 (4-methyl-piperazin-1-yl)-phenyl-acetonitrile 
• 33268-46-1 2-(4-bromophenyl)-2-phenylacetonitrile 
• 82954-08-3 2-(2,5-dimethylphenyl)-2-phenylacetonitrile 
• 725257-38-5 (4-ethyl-phenyl)-phenyl-acetonitrile 
• 113061-96-4 [N-(2-diethylamino-ethyl)-anilino]-phenyl-acetonitrile 
• 2450-55-7 diphenyl fumarodinitrile 
• 7584-72-7 meso-2,3-diphenylsuccinic acid 
• 4591-16-6 diphenylfumaronitrile 
• 15146-07-3 meso-1,2-dicyano-1,2-diphenylethane 
• 4578-79-4 2-(4-methoxyphenyl)-2-phenylacetonitrile 
• 490-55-1 amiphenazole 
• 101283-04-9 (4-ethoxy-phenyl)-phenyl-acetonitrile 
• 37489-32-0 4-methoxy-7-phenyl-7H-pyrimido[4,5-b][1,4]thiazin-6-ylamine 
• 54867-46-8 N-(4-amino-5-phenyl-thiazol-2-yl)-acetamide 

Relevant academic research and scientific papers

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Sydney and Sydney keepinone compounds as well as preparation method and application thereof (by machine translation)

The compound disclosed by the invention has a broad-spectrum bactericidal activity, for various plant fungal diseases and a preparation method and application I of the compound, and has excellent control effect on cucumber downy mildew, cucumber anthracnose, wheat powdery mildew, rice sheath blight, cucumber gray mold alone or with other agents . The compound of the present invention has a broad spectrum of fungicidal activity . The compound of, the present, invention has a broad spectrum of bactericidal activity alone or in combination with other agents. The compound of the present invention has excellent control. effect. (by machine translation)

Access to β-Ketonitriles through Nickel-Catalyzed Carbonylative Coupling of α-Bromonitriles with Alkylzinc Reagents

Herein, we report a nickel-catalyzed carbonylative coupling of α-bromonitriles and alkylzinc reagents with near stoichiometric carbon monoxide to give β-ketonitriles in good yields. The reaction is catalyzed by a readily available and stable nickel(II) pincer complex. The developed protocol tolerates substrates bearing a variety of functional groups, which would be problematic or incompatible with previous synthetic methods. Additionally, we demonstrate the suitability of the method for carbon isotope labeling by the synthesis of 13C-labeled β-ketonitriles and their transformation into isotopically labeled heterocycles.

Insilco screening, and Synthesis of 5-hydroxy-2-phenyl-1-benzofuran- 3(2H)-one derivatives as novel potent leads as anti-cancer agents

Insilco technique in chemistry plays a major role in the development of new lead molecules. Computational tools docking, virtual screening, ADMET prediction are untilised in the identification of new lead molecules. A series of new benzofuranone derivatives IVA-F, containing a heterocyclic substituent linked to benzofuranone nucleus at C-2 were synthesized as potential antitumor agents. These products were synthesized starting with benzene 1.4 diol. The structures of all compounds were established on the basis of analytical and spectral data. The synthesized compounds were tested against human skin carcinoma cell line (G361) and all were found to be more potent of which compound IV B and IV F was the most active.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF SEVERE PAIN

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of severe pain may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of chronic pain, generalized pain disorders, leukemia, cancer, chronic pain, chemotherapy induced pain, epilepsy, migraine, neuropathic pain, post herpetic neuralgia, neuralgia, pain, drug addiction, detoxification of drugs, Alzheimer's disease, multiple sclerosis, multiple sclerosis, restless legs syndrome (RLS), cluster headache, depression, fibromyalgia, amyotrophic lateral sclerosis (ALS), convulsions, partial seizures, mood-stabilizing agent and bipolar disorder.

Systematic study on alkyl iodide initiators in living radical polymerization with organic catalysts

Several low-molar-mass alkyl iodides were studied as initiating dormant species in living radical polymerization with organic catalysts. Primary, secondary, and tertiary alkyl iodides with different stabilizing groups (ester, phenyl, and cyano groups) were systematically studied for the rational design of initiating alkyl iodides. The activation rate constants of these alkyl iodides were experimentally determined for quantitative comparison. These alkyl iodides were used in the polymerizations of methyl methacrylate and butyl acrylate to examine their initiation ability in these polymerizations. A telechelic polymer was prepared using an alkyl iodide with a functional group. Alkyl iodides with multi-initiating sites were also studied.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF SEVERE PAIN

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of severe pain may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of chronic pain, generalized pain disorders, leukemia, cancer, chronic pain, chemotherapy induced pain, epilepsy, migraine, neuropathic pain, post herpetic neuralgia, neuralgia, pain, drug addiction, detoxification of drugs, Alzheimer's disease, multiple sclerosis, multiple sclerosis restless legs syndrome (RLS), cluster headache, depression, fibromyalgia, amyotrophic lateral sclerosis (ALS), convulsions, partial seizures, mood-stabilizing agent and bipolar disorder.

Synthesis and structure-activity relationships of A novel class of dithiocarbamic acid esters as anticancer agent

Based on a novel lead compound 4-methylpiperazine-1-carbodithioic acid 3-cyano-3,3-diphenylpropyl ester 1, the systematic structural modification was carried out. All the synthesized compounds were evaluated for their in-vitro anticancer activities on four to six different cell lines at three different concentrations. Most of the tested compounds could selectively inhibit the growth of HL-60 and Bel-7402 cell lines at a medium concentration. Four compounds (3f, 3g, 3n, and 5) were selected for the IC50 test, and the results revealed that three compounds (3g, 3n, and 5) showed almost the same or a slightly weaker activity than compound 1 against HL-60, and three compounds (3f, 3g, and 3n) showed >2-fold higher potency than compound 1 against Bel-7402. The in-vivo efficacy of 3n · HCl was evaluated with transplanted hepatocyte carcinoma 22 as an in-vivo test model. It was found that 3n · HCl could inhibit significantly the growth of tumor, and that this effect was dose-dependent. Meanwhile, the compound 3n · HCl showed low toxicity compared with compound 1 · HCl as evidenced by the little body-weight loss. These results confirmed that compound 3n · HCl is more potent than the lead compound 1 · HCl. Preliminary structure-activity relationships indicated that: a) Both nitrile group and the cyclic amine containing at least two nitrogens were indispensable moieties to keep the activity; b) substitution of the piperazine ring is unfavorable for the improvement of activity; c) the suitable linker joining the piperazinyl dithiocarboxyl and diphenylacetonitril group should be ethylene; d) a non-coplanar arrangement of the two benzene rings appears to be essential for activity. Based on a novel lead compound 4-methyl-piperazine-1-carbodithioic acid 3-cyano-3,3-diphenyl-propyl ester 1, the systematic structural modification was carried out. Compounds 3g and 3n were found to show more potent biological activities than lead compound 1. Some useful SARs were revealed Copyright

An unexpected result of the reaction of benzothioamide derivatives with 2-aryl-2-bromoacetonitriles

Unexpectedly, in the reaction of 2-bromo-2-phenylacetonitrile derivatives with 2 mol-equiv. of benzothioamide in DMSO, 3,5-diaryl-1,2,4-thiadiazoles were obtained in excellent yields (83-90%) and in short reaction times (5-10 min). It is found that, in DMF, a quite different reaction takes place and 2,5-diaryl-1,3-thiazol-4-amines are formed as the main products. Copyright