4592-94-3

Usage

Purification Methods

The nitrile is purified by dissolving in slightly alkaline H2O (charcoal), filtering and acidifying with HCl to give colourless needles (m 162-163o). It recrystallises from EtOH. With Me2SO4/KOH at 130o it gives 4-bromo-methoxycinnamylnitrile m 58.5-59.5o (from high boiling pet ether) [Fuson & Wolf J Am Chem Soc 61 1940 1939, Grathaus & Dains J Am Chem Soc 58 1334 1936]. [Beilstein 10 III 2998.]

InChI:InChI=1/C9H6BrNO/c10-8-3-1-7(2-4-8)9(12)5-6-11/h1-4H,5H2

Upstream product

• 151-50-8 potassium cyanide 
• 99-73-0 para-bromophenacyl bromide 
• 143-33-9 sodium cyanide 
• 99-90-1 para-bromoacetophenone 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 75-05-8 acetonitrile 
• 57-12-5 cyanide^(1-) 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 586-76-5 4-Bromobenzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 14063-78-6 3-(4-bromophenyl)-3-chloroprop-2-enal 
• 936368-52-4 (Z)-3-(4-bromophenyl)-3-chloro-2-propenenitrile 
• 5467-74-3 4-Bromophenylboronic acid 
• 109-77-3 malononitrile 

Downstream Products

• 74101-19-2 5-(4-bromo-phenyl)-2-[4-(4-chloro-phenyl)-thiazol-2-yl]-2H-pyrazol-3-ylamine 
• 74101-15-8 5-(4-bromo-phenyl)-2-[4-(4-bromo-phenyl)-thiazol-2-yl]-2H-pyrazol-3-ylamine 
• 65984-59-0 3-(4-bromophenyl)-3-hydroxypropanenitrile 
• 198709-47-6 5-(4-Bromo-phenyl)-2-(3-methyl-quinoxalin-2-yl)-2H-pyrazol-3-ylamine 
• 304018-33-5 2-amino-3-(4-bromo-benzoyl)-4,7-dihydro-5H-thieno[2,3-c]pyridine-6-carboxylic acid benzyl ester 
• 52200-18-7 2-(4-bromobenzoyl)-3-dimethylaminoacrylonitrile 
• 634915-15-4 4,6-dichloro-2-(3'-hydroxy-3'-phenylpropylamino)pyrimidine 
• 634915-19-8 2,4-dichloro-6-(3'-hydroxy-3'-phenylpropylamino)pyrimidine 
• 634915-20-1 6-[3'-(4''-bromophenyl)-3'-hydroxypropylamino]-2,4-dichloropyrimidine 
• 634915-16-5 2-[3'-(4''-bromophenyl)-3'-hydroxypropylamino]-4,6-dichloropyrimidine 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel 5-phenyl-1H-pyrazole derivatives as potential BRAFV600E inhibitors

A series of novel 5-phenyl-1H-pyrazole derivatives (5a-5u) containing niacinamide moiety were synthesized and evaluated for biological activity as potential BRAFV600E inhibitors. Among them, compound 5h exhibited the most potent inhibitory activity with an IC50 value of 0.33 μM for BRAFV600E. Antiproliferative assay results indicated that compound 5h has better antiproliferative activity against WM266.4 and A375 in vitro with IC50 value of 2.63 and 3.16 μM, respectively, being comparable with the positive control vemurafenib. Molecular docking of 5h into the BRAFV600E active site was performed to determine the probable binding mode. Furthermore, molecular docking and 3D QSAR study by means of DS 3.5 (Discovery Studio 3.5, Accelrys, Co. Ltd) explored the binding modes and the structure and activity relationship (SAR) of these derivatives.

Synthesis and biological evaluation of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives as potential BRAFV600E inhibitors

A series of novel N-(5-phenyl-1H-pyrazol-3-yl)benzenesulfonamide derivatives (5a–5l) were synthesized and developed as potential BRAFV600E inhibitors. Among them, compound 5l exhibited the most potent inhibitory activity with an IC50

Synthesis of Pyrazole Compounds by Using Sonication Method

A simple method for the synthesis of pyrazoles derivatives carried out by cyclization of cyanide with hydrazine hydrate by using sonication method. All the prepared compounds were characterized by 1H, 13C NMR and IR Spectroscopy.

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.).

Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives

A set of new dihydro-1H-pyrazolo[1,3-b]pyridine and pyrazolo[1,3-b]pyridine embelin derivatives was synthesized through a multicomponent reaction from natural embelin, 3-substituted-5-aminopyrazoles and aldehydes. The synthesized compounds were evaluated against three hematologic tumor cell lines, HEL (acute erythroid leukemia), K-562 (chronic myeloid leukemia) and HL-60 (acute myeloid leukemia), and five breast cancer cell lines (SKBR3, MCF-7, MDA-MB-231, BT-549, HS-578T). The primate non-malignant kidney Vero cell line was used as the control of cytotoxicity. From the obtained results, some structure–activity relationships were out-lined. Furthermore, in silico prediction of physicochemical properties and ADME parameters were determined for the derivatives with the best antiproliferative values.

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Selective Synthesis of β-Ketonitriles via Catalytic Carbopalladation of Dinitriles

A practical, convenient, and highly selective method of synthesizing β-ketonitriles from the Pd-catalyzed addition of organoboron reagents to dinitriles has been developed. This method provides excellent functional-group tolerance, a broad scope of substrates, and the convenience of using commercially available substrates. The method is expected to show further utility in future synthetic procedures.

AMIDE COMPOUND HAVING BET PROTEOLYSIS-INDUCING ACTION AND MEDICINAL APPLICATION THEREOF

The present invention aims to provide a compound that: has an excellent cytotoxic action on cancer cells, excellent induction of BET protein degradation in cancer cells, and an excellent binding-inhibiting action on BET protein and acetylated histone; and is effective as an anti-cancer agent, a BET protein degradation-inducing agent, or a BET protein inhibiting agent. A compound indicated in general formula (I) or a pharmacologically acceptable salt thereof. {In the formula, each symbol is as outlined in the Description.}

One-Pot Four-Component Coupling Approach to Polyheterocycles: 6 H-Furo[3,2- f]pyrrolo[1,2- d][1,4]diazepine

A novel polyheterocyclic chemical space, 6H-furo[3,2-f]pyrrolo[1,2-d][1,4]diazepine, was generated by a one-pot four-component coupling reaction where multiple bonds (three C-C, one C-O, and one C-N) were formed through a domino sequence. Two heterocyclic rings (furan and diazepine) were sequentially constructed from the monocyclic pyrrole derivative under environment-friendly reaction conditions to furnish the tricyclic fused scaffold.

Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives

A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.